cas 20238-83-9, 3-(4-HYDROXY-PHENYL)-PROPIONALDEHYDE

Articles about 20238-83-9Total 19 be found

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Hydroformylation of monosubstituted alkenes catalyzed by W-Rh bimetallic complex
By using a heterobimetallic catalyst, (CO)4(PEtPh 2)-W(μ-PPh2)Rh(CO)(PPh3), chemoselective hydroformylation of monosubstituted alkenes proceeds efficiently at room temperature under atmospheric pressure of CO/H
Yamane, Motoki,Yukimura, Noriaki,Ishiai, Hiroshi,Narasaka, Koichi
p. 540 - 541
(2006)
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Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst
This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.
Chen, Fen-Er,Gao, Peng,Ke, Miaolin,Liang, Guanfeng,Ru, Tong
(2021/08/26)

Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles
Pd(0) nanoparticles ca. 2 nm in diameter were obtained by the reduction of PdCl2 and Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium. The stability of Pd(0) NPs was evidenced in recycling experiments. Similar Heck coupling results were also obtained with the palladium compounds PdCl2(cod) and Pd(OAc)2 under the same conditions.
Tarnowicz, Stanis?awa,Alsalahi, Waleed,Mieczyńska, Ewa,Trzeciak, Anna M.
p. 5605 - 5612
(2017/08/26)

Switchable Site-Selective Catalytic Carboxylation of Allylic Alcohols with CO2
A switchable site-selective catalytic carboxylation of allylic alcohols has been developed in which CO2 is used with dual roles, both facilitating C?OH cleavage and as a C1 source. This protocol is characterized by its mild reaction conditions, absence of stoichiometric amounts of organometallic reagents, broad scope, and exquisite regiodivergency which can be modulated by the type of ligand employed.
van Gemmeren, Manuel,B?rjesson, Marino,Tortajada, Andreu,Sun, Shang-Zheng,Okura, Keisho,Martin, Ruben
supporting information
p. 6558 - 6562
(2017/05/29)

Organocatalytic, Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa-Michael Addition Sequence
An unprecedented enantioselective oxa-Michael reaction of α-tertiary alcohols using cinchona-alkaloid-based chiral bifunctional squaramide catalysts is reported. An oxidative dearomatization of phenol followed by an enantioselective oxa-Michael addition s
Reddy, Reddy Rajasekhar,Gudup, Satish Sonbarao,Ghorai, Prasanta
p. 15115 - 15119
(2016/11/25)

Enantioselective β-Alkylation of Aldehydes through an Organocatalyzed C-C Bond-Scission Reaction
A novel organocatalyzed C-C bond-scission reaction of saturated aldehydes containing a suitable leaving group at the β-position was used for the in situ formation of iminium intermediates, which were then captured by nucleophiles to achieve a direct enantioselective β-alkylation of aldehydes. Within short reaction times, the corresponding β-alkylated aldehyde products were obtained in high yields (48-87%) and with excellent enantioselectivities (84-98%).
Huang, Huicai,Abbaraju, Santhi,Zhao, John C.-G.
supporting information
p. 1379 - 1382
(2016/06/01)

H-type zeolite-catalyzed 1,4-addition of benzene derivatives to labile acrolein
The 1,4-addition of benzene derivatives to acrolein is a straightforward way to synthesize 3-arylpropanals. A survey of acid catalysts for the 1,4-addition of methoxy-substituted benzenes to acrolein revealed that H-Beta and H-Y were the most suitable catalysts. We hypothesized three side-reactions: (1) the double 1,4-addition of acrolein to the starting benzene derivatives, (2) the Friedel-Crafts-type alkylation to the desired product, and (3) the self-polymerization of acrolein. The type (3) side-reaction was inhibited by two different methods which kept the concentration of acrolein low in the reaction mixture or in the zeolite pores. First, acrolein monomers were in situ generated through the gradual monomerization of an acrolein cyclic trimer. Second, using a reaction solvent lowered the acrolein concentration in the zeolite pores due to the competitive adsorption. We discovered that the content of monomeric acrolein in a solvent was closely related to the polarity of the solvent. Actually, both methods improved the yields for the 1,4-additions of 1,3-dimethoxybenzene to acrolein. Other electron-rich benzene derivatives, such as phenol and N, N-dimethylaniline, were also applicable to the 1,4-addition reactions.
Hayashi, Daijiro,Narisawa, Tomoyuki,Masui, Yoichi,Onaka, Makoto
p. 460 - 471
(2016/04/26)

One-Pot, Enantioselective Synthesis of 2,3-Dihydroazulen-6(1H)-one: A Concise Access to the Core Structure of Cephalotaxus Norditerpenes
A one-pot enantioselective synthesis of cis-substituted 2,3-dihydroazulen-6(1H)-one is described. In this cascade reaction, an organocatalyzed asymmetric Michael reaction furnishes a highly optically pure nitrobutylphenol intermediate, which is converted into an annulated tropone species by sequential oxidative dearomatization, conjugate addition, electrocyclic ring opening and nitrous acid elimination in the same reaction vessel. Both aliphatic and aromatic nitroalkenes are good substrates for the one-pot reaction, and this protocol appears to be general for various phenylpropionaldehydes as well. In the case of asymmetrically substituted phenylpropionaldehydes, the regioselectivity is likely determined by both the steric and electronic properties of the substituents. This methodology is successfully applied to the synthesis of the tricyclic core structure of Cephalotaxus norditerpenes.
Yongsheng, Zheng,Ghazvini Zadeh, Ebrahim H.,Yuan, Yu
p. 2115 - 2119
(2016/05/09)

Scope and mechanism in palladium-catalyzed isomerizations of highly substituted allylic, homoallylic, and alkenyl alcohols
Herein we report the palladium-catalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols by means of a single catalytic system. The operationally simple reaction protocol is applicable to a broad range of substrates and displays a wide functional group tolerance, and the products are usually isolated in high chemical yield. Experimental and computational mechanistic investigations provide complementary and converging evidence for a chain-walking process consisting of repeated migratory insertion/β-H elimination sequences. Interestingly, the catalyst does not dissociate from the substrate in the isomerization of allylic alcohols, whereas it disengages during the isomerization of alkenyl alcohols when additional substituents are present on the alkyl chain.
Larionov, Evgeny,Lin, Luqing,Gune, Laure,Mazet, Clment
supporting information
p. 16882 - 16894
(2015/01/09)

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF
The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.
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(2014/10/15)

Highly chemo- and regioselective reaction of hydroxybenzenes in acidic ionic liquid
Highly chemo- and regioselective reaction of hydroxybenzenes with α,β-unsaturated compounds in acidic ionic liquid l-butyl-3- methylimidazolium hydrogen sulphate ([BMIM]HSO4) was reported for the first time. A series of oxa-Michael adducts and Friedel-Crafts alkylated products were synthesized with good yields. The acidic ionic liquid could be easily recycled for at least 5 times with only minor loss in activity.
Guo, Hui,Zhuang, Yu Wei,Cao, Jian,Zhang, Guo Bao
p. 2594 - 2596
(2013/10/22)

METHOD FOR PRODUCING A CROSS-COUPLING PRODUCT OF A BENZENOID DIAZONIUM SALT
The invention relates to a method for producing a cross-coupling product of a benzenoid dizonium salt according to the general formula (I), wherein the groups R1, R2, R3, R4, and R5 represent hydrogen, halogen, an alkyl, alkenyl, aryl, alkoxy, aryloxy, nitro, cyano, hydroxy, acetyl, and/or diazo groups independently of each, and X represents BF4, Cl, F, SO3CH3, CO2CH3, PF6, ClO2CH3, or CIO4, comprising the following steps: (a) providing a benzenoid amide, which with the exception of the diazo function has the same substituents R1, R2, R3, R4, and R5 as the benzenoid diazonium salt of the general formula (I), and hydrolytically cleaving the amide to form an amine or providing a corresponding amine, (b) diazotizing the amine thus obtained or provided with a nitrite, and (c) subsequently reacting the benzenoid diazonium salt with a coupling partner in the presence of a catalyst to form a cross-coupling product, wherein the coupling parter is represented by the general formula (II), R6, R7, and R8 are the same or different and represent hydrogen, carboxyalkyl groups, carboxyaryl groups, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, wherein the groups can each contain Si, N, S, O, and or halogen atoms, or R6 and R7 with the double bound form an aromatic ring, which can be provided with R8 and one to four further substituents, independently of each other, selected from the group comprising a straight-chain or branched (C1-C6) alkyl group, a (C3-C7) cycloalkyl group, a straight-chain or branched (C1-C6) alkenyl group, a straight-chain or branched (C1-C6) alkyoxy group, halogen, the hydroxy group, an amino, di(C1-C6) alkylamino, nitro, acetyl, cyan, benzyl, 4-methoxybenzyl, 4-nitrobenzyl, phenyl, and 4-methoxyphenyl group and represents Y=H, —B(OR)2, —SnR3, —ZnR, —SiR3, or Mg (halogen), and wherein at least the steps (b) and (c) are performed without intermediate isolation of an intermediate product. According to said method, cross-couplings can be performed more simply and with improved yield without the hydroxyl group in aromatic reactants containing hydroxyl groups having to be provided with a protective group.
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Paragraph 0049; 0050; 0051; 0052; 0053

(2013/03/26)

A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwort Plagiochasma appendiculatum
Alkenal double bond reductases (DBRs) catalyze the NADPH-dependent reduction of the α,β-unsaturated double bond of many secondary metabolites. Two alkenal double bond reductase genes PaDBR1 and PaDBR2 were isolated from the liverwort species Plagiochasma appendiculatum. Recombinant PaDBR2 protein had a higher catalytic activity than PaDBR1 with respect to the reduction of the double bond present in hydroxycinnamyl aldehydes. The residue at position 56 appeared to be responsible for this difference in enzyme activity. The functionality of a C56 to Y56 mutation in PaDBR1 was similar to that of PaDBR2. Further site-directed mutagenesis and structural modeling suggested that the phenol ring stacking between this residue and the substrate was an important determinant of catalytic efficiency.
Wu, Yifeng,Cai, Yuanheng,Sun, Yi,Xu, Ruixue,Yu, Haina,Han, Xiaojuan,Lou, Hongxiang,Cheng, Aixia
p. 3122 - 3128
(2013/09/23)

Pd-catalyzed arylation reactions with phenol diazonium salts: Application in the synthesis of diarylheptanoids
The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O- methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement.
Schmidt, Bernd,Hoelter, Frank,Kelling, Alexandra,Schilde, Uwe
supporting information; experimental part
p. 3357 - 3365
(2011/06/28)

Nornicotine-organocatalyzed aqueous reduction of α,β-unsaturated aldehydes
Nornicotine, a native component of tobacco and minor nicotine metabolite, was found to catalyze the chemoselective reduction of α,β-unsaturated aldehydes under homogeneous aqueous conditions. The Royal Society of Chemistry.
Brogan, Andrew P.,Dickerson, Tobin J.,Janda, Kim D.
p. 4952 - 4954
(2008/09/17)

Solid-Liquid Biphasic Hydroformylation of Olefins Catalyzed by Rhodium Carhonyl Complexes
Some polymer-anchored alkenes have been hydroformylated by carrying out the reaction in a high-pressure reactor equipped with a suitably designed vial. The solid substrates are converted to the corresponding oxo-aldehydes in high yields. In all cases the regioselectivity was strongly shifted towards the linear aldehyde when the rhodium carbonyl complex was modified with xantphos (3:1 or 4:1 P/Rh molar ratio). Treatment with 5% of trifluoroacetine acid in dichloromethane at room temperature removed quantitatively the oxo-product from the polymer support, which can be purified and reused.
Marchetti,Botteghi,Paganelli,Taddei
p. 1229 - 1236
(2007/10/03)

Bioactive pseudopeptidic analogues and cyclostereoisomers of osteogenic growth peptide C-terminal pentapeptide, OGP(10-14)
The osteogenic growth peptide (OGP) is a key factor in the mechanism of the systemic osteogenic response to local bone marrow injury. When administered in vivo, OGP stimulates osteogenesis and hematopoiesis. The C-terminal pentapeptide OGP(10-14) is the minimal amino acid sequence that retains the full OGP-like activity. Apparently, it is also the physiologic active form of OGP. Residues Tyr10, Phe12, Gly13, and Gly14 of OGP are essential for the OGP(10-14) activity. The present study explored the functional role of the peptide bonds, carboxyl and amino terminal groups, and conformational freedom in OGP(10-14). Transformations replacing the peptide bonds with surrogates such as ψ(CH2NH), ψ(CONMe), and ψ(CH2CH2) demonstrated that amide bonds do not contribute significantly to OGP(10-14) bioactivity. End-to-end cyclization yielded the fully bioactive cyclic pentapeptide c(Tyr-Gly-Phe-Gly-Gly). The retroinverso analogue c(Gly-Gly-phe-Gly-tyr), a cyclostereoisomer of c(Tyr-Gly-Phe-Gly-Gly), is at least as potent as the parent cyclic pentapeptide. The unique structure-activity relations revealed in this study suggest that the spatial presentation of the Tyr and Phe side chains has a major role in the productive interaction of OGP(10-14) and its truncated and conformationally constrained analogues with their cognate cellular target.
Chen, Yu-Chen,Muhlrad, Andras,Shteyer, Arie,Vidson, Marina,Bab, Itai,Chorev, Michael
p. 1624 - 1632
(2007/10/03)

THE BIOSYNTHESIS OF SCELETIUM ALKALOIDS IN SCELETIUM SUBVELUTINUM L. BOLUS
Six Sceletium (Mesembrine) alkaloids (1)-(6) are identified, together with N,N-dimethyltyramine (10), as constituents of Sceletium subvelutinum.The alkaloids (1)-(6) incroporate label from tyramine and 3-(-4-hydroxyphenyl)propionic acid (13) as expected; notably 3-(-4-hydroxyphenyl)propanal (15) is a more efficient alkaloid precursor than is the acid (13) and the aldehyde is deduced to be a key intermediate in the biosynthesis of Sceletium alkaloids.The N-methylamine (21) is an important late intermediate in the biosynthesis of Sceletium alkaloids, or is closely related to that intermediate.The amine (2) is less efficiently incorporated than (22)=(21) is.
Herbert, Richard B.,Kattah, Abdullah E.
p. 7105 - 7118
(2007/10/02)