cas 14436-32-9, 9-Decenoic acid | Articles data

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Synthesis of highly fluorinated fatty acid esters of glycerol:glycerol tripalmitate-F39
Glycerol tripalmitate-F39 has been prepared from glycerol and the acid chloride of RF-palmitic acid-F13 via a solid phase aluminum oxide catalyzed reaction. The product has been characterized by electrospray mass spectrometry and 1H, 19F and 13C NMR methods. A second, less efficient synthesis is reported in which a chain elongation strategy is employed after reaction of glycerol with the acid chloride of 9-decenoic acid.
Rastegar, Majid F.,Buchanan, Gerald W.,Bouffard, Melanie C.
p. 1042 - 1045
(2006)
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Synthesis of site-specifically13C labeled linoleic acids
Soybean lipoxygenase-1 (SLO-1) catalyzes the C–H abstraction from the reactive carbon (C-11) in linoleic acid as the first and rate-determining step in the formation of alkylhydroperoxides. While previous labeling strategies have focused on deuterium labeling to ascertain the primary and secondary kinetic isotope effects for this reaction, there is an emerging interest and need for selectively enriched13C isotopologues. In this Letter, we present synthetic strategies for site-specific13C labeled linoleic acid substrates. We take advantage of a Corey–Fuchs formyl to terminal13C-labeled alkyne conversion, using13CBr4as the labeling source, to reduce the number of steps from a previous fatty acid13C synthetic labeling approach. The labeled linoleic acid substrates are useful as nuclear tunneling markers and for extracting active site geometries of the enzyme–substrate complex in lipoxygenase.
Offenbacher, Adam R.,Zhu, Hui,Klinman, Judith P.
p. 4537 - 4540
(2016)
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EXTRAHEPATIC DELIVERY
One aspect of the present invention relates to a compound comprising an antisense strand which is complementary to a target gene; a sense strand which is complementary to said antisense strand; and one or more lipophilic monomers, containing one or more lipophilic moieties, conjugated to one or more positions on at least one strand, optionally via a linker or carrier. Another aspect of the invention relates to a method of gene silencing, comprising administering to a cell or a subject in need thereof a therapeutically effective amount of the lipophilic monomer-conjugated compound.
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Paragraph 0566; 0656

(2021/05/15)

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.
Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information
p. 709 - 713
(2019/01/25)

One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols
Herein, we report the nor-AZADO-catalyzed exhaustive aerobic oxidations of 1,2-diols to α-keto acids. Combining oxidation with transamination using dl-2-phenylglycine led to the synthesis of free α-amino acids (AAs) in one pot. This method enables the rapid and flexible preparation of a variety of valuable unnatural AAs, such as fluorescent AAs, photoactivatable AAs, and other functional AAs for bioorthogonal reactions.
Inada, Haruki,Furukawa, Keisuke,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information
p. 15105 - 15108
(2019/12/26)

RENEWABLY DERIVED POLYAMIDES AND METHODS OF MAKING THE SAME
Methods of making polyamides from renewable materials, such as natural oils, are generally disclosed herein. In some embodiments, the polyamides are nylon-10. In some such embodiments, nylon-10 is made by polymerizing 10-aminodecanoic acid, or esters thereof. In some further such embodiments, the 10-aminodecanoic acid monomers (or esters thereof) are derived from natural oils via the metathesis of unsaturated fatty acid moieties of the natural oil.
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Paragraph 0083

(2018/05/23)

METHOD OF SYNTHESISING AMINO ACID BY METATHESIS, HYDROLYSIS, THEN HYDROGENATION
A method of synthesising an amino acid from an unsaturated fatty compound I that includes at least the following steps: cross-metathesis with a short unsaturated compound II, one of compounds I or II comprising a nitrile function and the other of these compounds II or I an ester function, so as to obtain and recover at least one monounsaturated nitrile ester NEU; hydrolysis of the NEU in unsaturated acid nitrile NAU; hydrogenation of the NAU to saturated amino acid AA; and then purification of the AA, if applicable, in particular by crystallisation. Also, a polymer obtained by polymerisation using the amino acid synthesised according to the method.
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Paragraph 0182-0186

(2016/03/05)

Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes
The biocatalytic oxidative tandem decarboxylation of C7–C18dicarboxylic acids to terminal C5–C16dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene; scale-up allowed the isolation of 1,15-hexadecadiene and 1,11-dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.
Dennig, Alexander,Kurakin, Sara,Kuhn, Miriam,Dordic, Andela,Hall, Mélanie,Faber, Kurt
supporting information
p. 3473 - 3477
(2016/07/29)

Ring-closing metathesis based total synthesis of ciliatamides A and B and their structural confirmation
Protecting group dependant ring-closing metathesis based approach to the total synthesis of the revised structures of ciliatamides A and B has been described. The current synthetic strategy utilizes the amino acid as starting material to introduce both the stereogenic centers. However, usage of non-racemizing reagents (EDC·HCl, HATU/NMM); for amide coupling and Grubbs' second generation catalyst for caprolactam ring synthesis makes the present approach more convenient to get the correct conclusion on absolute stereochemistry. Thus, on the basis of similar optical rotation values with the Lindsley's reported data, this synthesis further supported for the actual stereochemistry of both ciliatamides A and B is (R,R).
Avula, Krishnakumari,Mohapatra, Debendra K.
supporting information
p. 1715 - 1717
(2016/04/04)

METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS
The invention relates to a method for preparing a compound of formula (I), wherein n is an integer from 1 to 21,said method comprises reacting a light olefin fraction, in the presence of a metathesis catalyst, with a compound having from 10 to 24 carbon atoms, of the following formula (II): wherein, n is an integer from 1 to 21,R corresponds to a hydrogen atom or an alkyl or alkenyl chain from 1 to20 carbon atoms optionally substituted by at least one hydroxyl group, said compound of formula (II) being used alone or in a mixture of compounds of formula (II).
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Paragraph 0071-0081

(2015/12/07)

GLYCITAN ESTERS OF UNSATURATED FATTY ACIDS AND THEIR PREPARATION
A method is disclosed for making an unsaturated glycitan ester by reacting intramolecular condensates of glycitols having four or more carbons with a metathesis-derived unsaturated fatty acid in the presence of an alkaline catalyst and under conditions sufficient to form the aforesaid unsaturated glycitan fatty ester. A composition is also disclosed comprising a compound of the following structure: wherein R1 is hydrogen, alkyl, aryl or (CH2)1-9—COOR5; wherein R5 is wherein R2, R3 and R4 are hydrogen, or —(O)C—(CH2)m—CH═CH—R1 or —(CH2CH2O)nH or mixtures thereof; wherein m is 1 to 9; and wherein n is 1 to 100.
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Paragraph 0089; 0090

(2014/09/30)

ESTERAMINES AND DERIVATIVES FROM NATURAL OIL METATHESIS
Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.
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Page/Page column 22

(2012/05/20)

Selective oxoammonium salt oxidations of alcohols to aldehydes and aldehydes to carboxylic acids
The oxidation of alcohols to aldehydes using stoichiometric 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in CH2Cl2 at room temperature is a highly selective process favoring reaction at the carbinol center best able to accommodate a positive charge. The oxidation of aldehydes to carboxylic acids by 1 in wet acetonitrile is also selective; the rate of the process correlates with the concentration of aldehyde hydrate. A convenient and high yield method for oxidation of alcohols directly to carboxylic acids has been developed.
Qiu, Joseph C.,Pradhan, Priya P.,Blanck, Nyle B.,Bobbitt, James M.,Bailey, William F.
supporting information; experimental part
p. 350 - 353
(2012/03/09)

Enzyme-substrate complementarity governs access to a cationic reaction manifold in the P450BM3-catalysed oxidation of cyclopropyl fatty acids
The products of cytochrome P450BM3-catalysed oxidation of cyclopropyl-containing dodecanoic acids are consistent with the presence of a cationic reaction intermediate, which results in efficient dehydrogenation of the rearranged probes by the enzyme. These results highlight the importance of enzyme-substrate complementarity, with a cationic intermediate occurring only when the probes used begin to diverge from ideal substrates for this enzyme. This also aids in reconciling literature reports supporting the presence of cationic intermediates with certain cytochrome P450 enzyme/substrate pairs.
Cryle, Max J.,Hayes, Patricia Y.,De Voss, James J.
supporting information
p. 15994 - 15999
(2013/02/21)

METHOD FOR SYNTHESISING 9-AMINONONANOIC ACID OR THE ESTERS THEREOF FROM NATURAL UNSATURATED FATTY ACIDS
The invention relates to a method for synthesizing 9-aminononanoic acid or the esters thereof from natural unsaturated fatty acids, comprising at least one step of metathesis of the natural fatty acid and an oxidation step by oxidative cleaving. Said synthetic method uses widely available renewable starting materials and hence economical.
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Page/Page column 6

(2011/05/08)

TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates
We present a simple, mild, and highly effective method for the direct conversion of primary alcohols to carboxylic acids. TPAP serves as the catalyst, and NMO?H2O plays a dual role, acting as the co-oxidant and as a reagent for aldehyde hydrate stabilization. This previously unknown stabilizing effect of geminal diols by N-oxides is the key for the efficiency of the overall transformation.
Schmidt, Andrea-Katharina C.,Stark, Christian B. W.
supporting information; experimental part
p. 4164 - 4167
(2011/10/08)

METHOD FOR THE SYNTHESIS OF DIACIDS OR DIESTERS FROM NATURAL FATTY ACIDS AND/OR ESTERS
The invention relates to a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x—COOR, in which n is an integer between 5 and 14, R is either H or an alkyl radical of 1 to 4 carbon atoms, from natural long-chain monounsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule of the general formula CH3—(CH2)n—CHR1—CH2—CH═CH—(CH2)p—COOR, in which R is H or an alkyl radical with 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are equal or different and are indices between 2 and 11. The method comprises: during a first step, converting the natural fatty acid or ester by pyrolysis or by ethenolysis, into a ω-monounsaturated fatty acid or ester of the general formula CH2═CH—(CH2)m—COOR, in which m is equal to p or p+1, depending on the nature of the processed fatty acid/ester and the conversion used; during a second step, submitting the product thus obtained to a metathesis or homometathesis reaction for obtaining a compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)m—COOR, or cross-metathesis with a compound of formula R2OOC—(CH2)r—CH═CH—R3, in which R2 is either H or an alkyl radical front with 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R3 is H, CH3 or COOR2, thus defining a cyclic or molecule or not, in order to obtain an unsaturated compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)r—COOR2, and during a third step, converting the unsaturated compound into a saturated compound by hydrogenation of the double bond.
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Page/Page column 6

(2010/12/29)

2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone
Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) such as5-Me-IBX (1g), 5-MeO-IBX (1h), and 4,5-Me2-IBX were superior to IBX 1a as catalysts for the oxidation of alcohols with Oxone (a trad emark of DuPont) under nonaqueous conditions, although Oxone was almost insoluble in most organic solvents. The catalytic oxidation proceeded more rapidly and cleanly in nitromethane. Furthermore, 2-iodoxybenzenesulfonic acid (IBS, 6a) was much more active than modified IBXs. Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with Oxone in nonaqueous nitromethane, acetonitrile, or ethyl acetate in the presence of 0.05-5molpercentof 6a, which was generated in situ from 2-iodobenzenesulfonic acid (7a) or its sodium salt. Cycloalkanones could be further oxidized to α,β- cycloalkenones or lactones by controlling the amounts of Oxone under the same conditions as above. When Oxone was used under nonaqueous conditions, Oxone wastes could be removed by simple filtration. Based on theoretical calculations, we considered that the relatively ionic character of the intramolecular hypervalent iodine-OSO2 bond of IBS might lower the twisting barrier of the alkoxyperiodinane intermediate 16.
Uyanik, Muhammet,Akakura, Matsujiro,Ishihara, Kazuaki
supporting information; experimental part
p. 251 - 262
(2009/06/28)

Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus
The four major components present in scent gland extracts of the male Costa Rica longwing butterflies Heliconius cydno and Heliconius pachinus were identified as 12- and 14-membered macrolides containing a C18-carbon skeleton. By use of micro-reactions and spectrometric examinations, structural proposals were made and subsequently proven by synthesis, using ring-closing-metathesis as the key steps. These macrolides, (9Z,11E,13S)- octadeca-9,11-dien-13-olide (5, S-coriolide), (9Z,11E,13S,15Z)-octadeca-9,11,15- trien-13-olide (6), (9Z,13S)-octadec-9-en-13-olide (13), and (9Z,11S)-octadec-9-en-11-olide (25), are biosynthetically obviously derived from oleic, linoleic, and linolenic acids. Their absolute configurations were determined by gas chromatographic investigations on chiral phases, showing all to possess (S)-configuration. The Royal Society of Chemistry.
Schulz, Stefan,Yildizhan, Selma,Stritzke, Katja,Estrada, Catalina,Gilbert, Lawrence E.
p. 3434 - 3441
(2008/09/19)

Oxidation of alcohols with catalytic amounts of IBX
Herein we present a catalytic IBX-based method for the oxidation of alcohols. Using this system a variety of benzylic alcohols were transformed to aldehydes in good yields whereas secondary alcohols were easily converted to ketones. Primary aliphatic alcohols were oxidised to the corresponding carboxylic acids. 2-lodobenzoic acid can also be used instead of IBX. Georg Thieme Verlag Stuttgart.
Schulze, Agnes,Giannis, Athanassios
p. 257 - 260
(2007/10/03)

Concise total synthesis of (+)-carpamic acid
We report herein an efficient enantioselective synthesis of (+)-carpamic acid, with nine steps as the longest linear sequence, the key strategy being based on a novel sequence of a cross-metathesis (CM) reaction and a subsequent cyclizing reductive amination to form the piperidine ring.
Randl, Stefan,Blechert, Siegfried
p. 1167 - 1169
(2007/10/03)

Asymmetric dihydroxylation of vinyl sulfones: Routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones
The asymmetric dihydroxylation of α,β-unsaturated sulfones under Sharpless conditions affords enantioenriched α-hydroxyaldehydes in a complex mixture of dimeric species. These mixtures undergo olefination generating the corresponding α,β-unsaturated esters or furan-2(5H)-ones with high levels of enantiomeric excess. The application of this method for the rapid stereoselective synthesis of the furanone natural products; quercus lactone and maritolide, are described.
Evans, Paul,Leffray, Mélanie
p. 7973 - 7981
(2007/10/03)

High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
A method of preparing a catalyst of the formula comprising:reacting a compound of the formula (XX1MLnL1m)p with a phosphorane of the formula wherein:M is Os or Ru;R and R1 are either the same or different and are(a) hydrogen,(b) a group selected from C2-C20 alkenyl, C2-C20 alkynyl, C1-C20 alkyl, aryl, C1-C20 carboxylate, C2-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl, or C1-C20 alkylsulfinyl, or(c) one of the groups listed in (b) substituted with C1-C5 alkyl, halogen, C1-C5 alkoxy, unsubstituted phenyl, halogen substituted phenyl, C1-C5 alkyl substituted phenyl, or C1-C5 alkoxy substituted phenyl;R4, R5, and R6 are either the same or different and are each unsubstituted or substituted hydrocarbon wherein the hydrocarbon is selected from the group consisting of aryl, C1-C6 alkyl, C1-C6 alkoxy, and phenoxy and the hydrocarbon substitution is selected from the group consisting of halogen, C1-C3 alkyl, C1-C3 alkoxy, unsubstituted phenyl, halogen substituted phenyl, C1-C5 alkyl substituted phenyl, and C1-C5 alkoxy substituted phenyl;X and X1 are either the same or different and are any anionic ligand;L is any neutral electron donor;L1 is a trialkylphosphine ligand where at least one of the alkyl groups is a secondary alkyl or a cycloalkyl;n and m are independently 0-4, provided n+m=2, 3 or 4; andp is an integer equal to or greater than 1.
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Page 16-17

(2010/01/31)

IBX-mediated oxidation of primary alcohols and aldehydes to form carboxylic acids
Under mild conditions and without the use of toxic metals, the oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids with 1-hydroxy-1,2-benziodoxole-3(1H)-one-1-oxide (IBX) proceeds in the presence of 1-hydroxypyridine or N-hydroxysuccinimide (see scheme). The reaction tolerates a wide variety of functional groups.
Mazitschek, Ralph,Muelbaier, Marcel,Giannis, Athanassios
p. 4059 - 4061
(2007/10/03)

Cyclization of 9-Substituted Decanoic Acid Derivatives to 9-Decanolide and 9-Decanelactam
Several standard and some novel cyclization reactions have been applied to 9-substituted decanoic acids to establish which are the optimum procedures for lactonization and lactamization at 80 deg C under identical high-dilution conditions.The methods of Galli-Mandolini and Kellogg (cyclization of 9-bromodecanoate ion), Gerlach (cyclization of S-2-pyridyl 9-hydroxydecanethioate in the presence of AgClO4), and Yamaguchi (activation of the carboxyl group as a mixed anhydride) in the presence of an excess of DMAP appear to be the most useful for the preparation of the 10-membered lactone, phoracantolide I, under these conditions.Analogously, treatment of S-2-pyridyl 9-azidodecanethionate with Sn(SePh)3(1-) afforded the best yield of the 10-membered lactam.The mixed anhydrides RCOOCOAr (Ar = 2,4,6-trichlorophenyl) are more reactive than thioesters RCOSPy (Py = 2-pyridyl) with benzyl alcohol or benzylamine; it is confirmed that the addition of DMAP activates the reaction of alcohols with mixed anhydrides much more than with pyridyl thioesters, while the addition of Ag(1+) strongly activates RCOSPy in relation to either RCOOCOAr or RCOOSO2Mes.
Bartra, Marti,Vilarrasa, Jaume
p. 5132 - 5138
(2007/10/02)

Ant venom alkaloids from Monomorium species: Natural insecticides
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Bacos,Basselier,Celerier,Lange,Marx,Lhommet,Escoubas,Lemaire,Clement
p. 3061 - 3064
(2007/10/02)

THE PHOTOCHEMISTRY OF α-OXIMINO KETONES. 2-OXIMINOCYCLODODECANONE
Irradiation of (E)-2-oximinocyclododecanone (12) in methanol with a medium pressure mercury lamp gives (Z)-2-oximinocyclododecanone (13), 12-hydroxybicyclododecan-11-one oxime (14), (2-oxocyclodecane)acetonitrile (17), and methyl 10-undecenoate (18).The nitrile 17 has been shown to be formed from the oxime 14 on irradiation of the latter in methanol or on treatment with acetic anhydride in pyridine.It is proposed that the ester 18 arises, like oxime 14, via γ-H-abstraction by the O atom of the CO group of the α-oximino ketone 12, and that the primary photochemical processes under the conditions used are limited to geometrical isomerization about the C=N bond and such γ-H-abstraction.
Yates, Peter,Wong, James,McLean, Stewart
p. 3357 - 3364
(2007/10/02)

THE SYNTHESIS OF PGF1α BY RE-STRUCTURING OF CASTOR OIL
Castor oil has been transformed - via methyl ricinoleate - to PGF1α by strategy wherein 16 of the 18 carbons of the castor oil backbone are incorporated in the C-20 PGF1α, involving, inter alia, a novel procedure for the regiospecific functionalisation of terminal olefins, a novel degradation of aldehyde to lower acid and strategies useful for the generation of the highly functionalised prostanoid system, which specially illustrate the utility of MEM protecting group in diverse types of chemical transformations.Additionally, this work describes the preparation of synthons having potential utility and the synthesis of novel homo-PGF1α.
Ranganathan, D.,Ranganathan, S.,Mehrotra, M. M.
p. 1869 - 1876
(2007/10/02)