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128-50-7

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128-50-7 Usage

Description

NOPOL, also known as 10-Hydroxymethylene-2-Pinene, is a naturally occurring compound found in carrots. It is characterized by its mild, woody, camphoraceous odor and possesses unique chemical properties that make it a versatile substance with various applications across different industries.

Uses

Used in the Flavor and Fragrance Industry:
NOPOL is used as a key ingredient in the flavor and fragrance industry for its distinct and pleasant odor. Its woody and camphoraceous scent adds depth and complexity to perfumes, colognes, and other fragrance products.
Used in the Pharmaceutical Industry:
NOPOL is used as a potential therapeutic agent in the pharmaceutical industry due to its unique chemical properties. It can be further researched and developed for various medicinal applications, such as treating specific health conditions or as a component in the formulation of new drugs.
Used in the Agricultural Industry:
NOPOL, being a natural compound, can be utilized in the agricultural industry as a component in the development of eco-friendly and sustainable pest control solutions. Its unique properties may offer an alternative to traditional chemical pesticides, promoting a more environmentally friendly approach to crop protection.
Used in the Cosmetics Industry:
In the cosmetics industry, NOPOL can be used as a natural additive for various cosmetic products, such as creams, lotions, and shampoos. Its pleasant odor and potential therapeutic properties can enhance the sensory experience and provide additional benefits to users.
Used in the Food and Beverage Industry:
NOPOL can be employed in the food and beverage industry as a natural flavoring agent, adding a unique taste and aroma to various products. Its woody and camphoraceous scent can be used to enhance the flavor profile of beverages, confectioneries, and other food items.

Check Digit Verification of cas no

The CAS Registry Mumber 128-50-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 8 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 128-50:
(5*1)+(4*2)+(3*8)+(2*5)+(1*0)=47
47 % 10 = 7
So 128-50-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3/t9-,10-/m1/s1

128-50-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name NOPOL

1.2 Other means of identification

Product number -
Other names 6,6-dimethyl-2-norpinene-2-ethano

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:128-50-7 SDS

128-50-7Synthetic route

formaldehyd
50-00-0

formaldehyd

Beta-pinene
177698-19-0

Beta-pinene

nopol
128-50-7

nopol

Conditions
ConditionsYield
With iron(III) phosphate In acetonitrile at 80℃; for 4h; Prins condensation;100%
With mesoporous SnSBA-15(5) In toluene at 89.84℃; for 6h; Prins reaction;96.7%
at 150℃;61%
benzyl nopyl ether

benzyl nopyl ether

nopol
128-50-7

nopol

Conditions
ConditionsYield
With hydrogen; benzyl bromide; Pd<*>MCM-48 In methanol under 760.051 Torr;95%
With Na2K-SG(I) In tetrahydrofuran at 20℃; Inert atmosphere;
2-<2-(methoxymethoxy)ethyl>-6,6-dimethylbicyclo<3.1.1>hept-2-ene
77661-66-6

2-<2-(methoxymethoxy)ethyl>-6,6-dimethylbicyclo<3.1.1>hept-2-ene

nopol
128-50-7

nopol

Conditions
ConditionsYield
zirconium(IV) chloride In isopropyl alcohol for 4h; Heating;93%
tert-butyl-[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-dimethyl-silane

tert-butyl-[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-dimethyl-silane

nopol
128-50-7

nopol

Conditions
ConditionsYield
With zirconium(IV) chloride In acetonitrile at 20℃; for 0.333333h;87%
nopyl acetate
128-51-8

nopyl acetate

nopol
128-50-7

nopol

Conditions
ConditionsYield
With lithium aluminium tetrahydride86%
(saponification);
[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-trimethyl-silane
69978-56-9

[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-trimethyl-silane

nopol
128-50-7

nopol

Conditions
ConditionsYield
With tris paraperiodate In benzene for 0.166667h; Heating;85%
4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-phenyl-methyl}-biphenyl
693272-53-6

4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-phenyl-methyl}-biphenyl

nopol
128-50-7

nopol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 7h;83%
4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-diphenyl-methyl}-biphenyl
693272-54-7

4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-diphenyl-methyl}-biphenyl

nopol
128-50-7

nopol

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 3h;82%
6,6-dimethyl-2-[2-(3-methyl-but-2-enyloxy)-ethyl]-bicyclo[3.1.1]hept-2-ene

6,6-dimethyl-2-[2-(3-methyl-but-2-enyloxy)-ethyl]-bicyclo[3.1.1]hept-2-ene

nopol
128-50-7

nopol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 1.5h;78%
Conditions
ConditionsYield
With Cr and Fe containing metal organic framework MIL-101; air In acetonitrile at 80℃; for 30h; Catalytic behavior; Reagent/catalyst;A 63.75%
B 21.25%
6,6-dimethyl-2-(p-tolylsulphonylethyl)bicyclo<3.1.1>hept-2-ene
74892-00-5, 103364-60-9

6,6-dimethyl-2-(p-tolylsulphonylethyl)bicyclo<3.1.1>hept-2-ene

A

2-ethylene-6,6-dimethylbicyclo<3.1.1>hept-2-ene
473-00-7

2-ethylene-6,6-dimethylbicyclo<3.1.1>hept-2-ene

B

1-ethyl-4-isopropylbenzene
4218-48-8

1-ethyl-4-isopropylbenzene

C

nopol
128-50-7

nopol

cis-2-hydroxy-8,8-dimethyltricyclo<5.1.1.02,5>nonane
110259-86-4, 127380-71-6

cis-2-hydroxy-8,8-dimethyltricyclo<5.1.1.02,5>nonane

E

trans-3-hydroxy-6,6-dimethylnopinane-2-spiro-1'-cyclopropane
35117-82-9, 127380-70-5, 127380-72-7

trans-3-hydroxy-6,6-dimethylnopinane-2-spiro-1'-cyclopropane

Conditions
ConditionsYield
With lithium aluminium tetrahydride; sodium acetate; acetic acid Mechanism;
6,6-dimethyl-2-(p-tolylsulphonylethyl)bicyclo<3.1.1>hept-2-ene
74892-00-5, 103364-60-9

6,6-dimethyl-2-(p-tolylsulphonylethyl)bicyclo<3.1.1>hept-2-ene

A

1-ethyl-4-isopropylbenzene
4218-48-8

1-ethyl-4-isopropylbenzene

B

nopol
128-50-7

nopol

cis-2-hydroxy-8,8-dimethyltricyclo<5.1.1.02,5>nonane
110259-86-4, 127380-71-6

cis-2-hydroxy-8,8-dimethyltricyclo<5.1.1.02,5>nonane

D

trans-3-hydroxy-6,6-dimethylnopinane-2-spiro-1'-cyclopropane
35117-82-9, 127380-70-5, 127380-72-7

trans-3-hydroxy-6,6-dimethylnopinane-2-spiro-1'-cyclopropane

Conditions
ConditionsYield
With lithium aluminium tetrahydride; sodium acetate; acetic acid 1.) 70 deg C, 12 h, 2.) ether; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;
Beta-pinene
177698-19-0

Beta-pinene

nopol
128-50-7

nopol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 180 - 220 °C
2: (saponification)
View Scheme
formaldehyd
50-00-0

formaldehyd

Beta-pinene
177698-19-0

Beta-pinene

A

camphene
79-92-5

camphene

B

nopol
128-50-7

nopol

Conditions
ConditionsYield
With zirconia pillared zirconium phosphate ZrO2-ZrP-a-150 In toluene at 80℃; for 4h; Reagent/catalyst;
Dimethoxymethane
109-87-5

Dimethoxymethane

nopol
128-50-7

nopol

2-<2-(methoxymethoxy)ethyl>-6,6-dimethylbicyclo<3.1.1>hept-2-ene
77661-66-6

2-<2-(methoxymethoxy)ethyl>-6,6-dimethylbicyclo<3.1.1>hept-2-ene

Conditions
ConditionsYield
zirconium(IV) chloride at 20℃; for 6.5h;97%
nopol
128-50-7

nopol

1-bromo-2-(6,6-dimethylbicyclo[3.1.1.]hept-2-en-2-yl)ethane

1-bromo-2-(6,6-dimethylbicyclo[3.1.1.]hept-2-en-2-yl)ethane

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; Cooling with ice;96%
With phosphorus tribromide In petroleum
nopol
128-50-7

nopol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl methanesulfonate

[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 24.3h;95%
nopol
128-50-7

nopol

bis(β-trimethylsilylethanesulfonyl)imide
548462-13-1

bis(β-trimethylsilylethanesulfonyl)imide

C21H43NO4S2Si2

C21H43NO4S2Si2

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 50℃; Mitsunobu reaction;93%
nopol
128-50-7

nopol

2-(6,6-Dimethylbicyclo<3.1.1>hept-2-ene)acetaldehyde
30897-75-7

2-(6,6-Dimethylbicyclo<3.1.1>hept-2-ene)acetaldehyde

Conditions
ConditionsYield
With zinc bismuthate In toluene for 2.5h; Heating;90%
With sodium hydrogencarbonate; Dess-Martin periodane at 0℃; for 4h;75%
nopol
128-50-7

nopol

dihydronopol
4747-61-9

dihydronopol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 20℃; Solvent; Reagent/catalyst;88.9%
With hydrogen; nickel
nopol
128-50-7

nopol

4-phenylbenzhydrol
7598-80-3

4-phenylbenzhydrol

4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-phenyl-methyl}-biphenyl
693272-53-6

4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-phenyl-methyl}-biphenyl

Conditions
ConditionsYield
With ytterbium(III) triflate In dichloromethane at 20℃; for 5h;85%
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

nopol
128-50-7

nopol

2,4,6-Tris-[2-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-[1,3,5]triazine

2,4,6-Tris-[2-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-[1,3,5]triazine

Conditions
ConditionsYield
With sodium85%
nopol
128-50-7

nopol

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

2-[2-(4-methoxy-benzyloxy)-ethyl]-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene

2-[2-(4-methoxy-benzyloxy)-ethyl]-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
With ytterbium(III) triflate In dichloromethane at 20℃; for 24h; Etherification;83%
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

nopol
128-50-7

nopol

1,3,5-Tris-[2-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethyl]-[1,3,5]triazinane-2,4,6-trione

1,3,5-Tris-[2-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethyl]-[1,3,5]triazinane-2,4,6-trione

Conditions
ConditionsYield
With sodium hydride81%
nopol
128-50-7

nopol

dimethyl sulfate
77-78-1

dimethyl sulfate

2-(2-methoxyethyl)-6,6-dimethylbicyclo<3.1.1>hept-2-ene
81991-72-2

2-(2-methoxyethyl)-6,6-dimethylbicyclo<3.1.1>hept-2-ene

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In hexane; water for 4h;80%
nopol
128-50-7

nopol

1-(4-methoxyphenyl)-1-phenylmethanol
720-44-5

1-(4-methoxyphenyl)-1-phenylmethanol

2-{2-[(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene

2-{2-[(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene

Conditions
ConditionsYield
With ytterbium(III) triflate In dichloromethane at 20℃; for 0.5h;76%
nopol
128-50-7

nopol

4-biphenylyldiphenylmethanol
38696-14-9

4-biphenylyldiphenylmethanol

4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-diphenyl-methyl}-biphenyl
693272-54-7

4-{[2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-diphenyl-methyl}-biphenyl

Conditions
ConditionsYield
With ytterbium(III) triflate In dichloromethane for 12h; Heating;76%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

nopol
128-50-7

nopol

2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl 4-nitrobenzoate
79552-27-5

2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl 4-nitrobenzoate

Conditions
ConditionsYield
With sodium carbonate; palladium; silver(l) oxide at 80℃; for 48h; Molecular sieve;75%
Ru((CH3C6H4CH(CH3)2)Cl2(P(C6H5)2CH2CH2Si(CH3)2H))
151753-29-6

Ru((CH3C6H4CH(CH3)2)Cl2(P(C6H5)2CH2CH2Si(CH3)2H))

nopol
128-50-7

nopol

Ru((CH3C6H4CH(CH3)2)Cl2(P(C6H5)2CH2CH2Si(CH3)2OC11H17))

Ru((CH3C6H4CH(CH3)2)Cl2(P(C6H5)2CH2CH2Si(CH3)2OC11H17))

Conditions
ConditionsYield
In dichloromethane a stirred soln. of Ru-compd. is treated with nopol for 36 h (N2);65%
nopol
128-50-7

nopol

methyl hypofluorite
36336-08-0

methyl hypofluorite

2-((1R,2S,3S,5R)-2-Fluoro-3-methoxy-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl)-ethanol

2-((1R,2S,3S,5R)-2-Fluoro-3-methoxy-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl)-ethanol

Conditions
ConditionsYield
In methanol; dichloromethane; acetonitrile40%
nopol
128-50-7

nopol

A

2-ethylene-6,6-dimethylbicyclo<3.1.1>hept-2-ene
473-00-7

2-ethylene-6,6-dimethylbicyclo<3.1.1>hept-2-ene

B

1-ethyl-4-isopropylbenzene
4218-48-8

1-ethyl-4-isopropylbenzene

Conditions
ConditionsYield
With acetic acid In methanol at 62.5℃;A 31%
B 6%
hexafluoropropene-diethylamine adduct
309-88-6

hexafluoropropene-diethylamine adduct

nopol
128-50-7

nopol

2,3,3,3-Tetrafluoro-propionic acid 2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethyl ester

2,3,3,3-Tetrafluoro-propionic acid 2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane Ambient temperature;30%
2-(N,N-dimethylamino)ethyl bromide
5459-68-7

2-(N,N-dimethylamino)ethyl bromide

nopol
128-50-7

nopol

{2-[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-yl)-ethoxy]-ethyl}-dimethyl-amine
53207-04-8

{2-[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-yl)-ethoxy]-ethyl}-dimethyl-amine

Conditions
ConditionsYield
(i) NaNH2, (ii) H2, Pt; Multistep reaction;
Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

nopol
128-50-7

nopol

[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-trimethyl-silane
69978-56-9

[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethoxy]-trimethyl-silane

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In benzene

128-50-7Downstream Products

128-50-7Related news

Nanosized sulfated zinc ferrite as catalyst for the synthesis of NOPOL (cas 128-50-7) and other fine chemicals09/30/2019

A nanosized highly ordered mesoporous zinc ferrite (ZnFe 2 O 4 ; ZF) was synthesized via co-precipitation method, further sulfated with ammonium sulfate solution to obtain sulfated ZF (SZF) and have been used for the synthesis of nopol by Prins condensation of β-pinene and paraf...detailed

Kinetics of the NOPOL (cas 128-50-7) synthesis by the Prins reaction over tin impregnated MCM-41 catalyst09/29/2019

The kinetics of the nopol synthesis by Prins condensation of β-pinene and paraformaldehyde over Sn-MCM-41 synthesized by impregnation was evaluated using the initial reaction rate method. The reaction rate equation obtained from a kinetic model based on the Langmuir–Hinshelwood formalism with ...detailed

Mixed Oxides of Hydrotalcites as Catalysts for NOPOL (cas 128-50-7) Epoxidation10/01/2019

Mixed oxides catalysts derived from Mg/Al hydrotalcite-type materials with molar ratios of 1, 2, 3 and 4 were synthesized, characterized and tested in nopol epoxidation. A combined oxidant of hydrogen peroxide and acetonitrile was used in the presence of acetone and water as solvents. Catalysts ...detailed

Transformations of epoxide derived from NOPOL (cas 128-50-7) over askanite-bentonite clay09/27/2019

Transformations of epoxide derived from nopol in the presence of natural askanite-bentonite clay were studied. The major products of the isomerization in the cold are diols possessing a p-menthane skeleton, which are readily converted into bicyclic ethers when the reaction is carried out at room...detailed

Alleviating patch overfitting with automatic test generation: a study of feasibility and effectiveness for the NOPOL (cas 128-50-7) repair system09/25/2019

Among the many different kinds of program repair techniques, one widely studied family of techniques is called test suite based repair. However, test suites are in essence input-output specifications and are thus typically inadequate for completely specifying the expected behavior of the program...detailed

128-50-7Relevant articles and documents

Condensation reactions assisted by acidic hydrogen bonded hydroxyl groups in solid tin(ii)hydroxychloride

Marakatti, Vijaykumar S.,Shanbhag, Ganapati V.,Halgeri, Anand B.

, p. 10795 - 10800 (2013)

Tin(ii)hydroxychloride is reported as a heterogeneous Bronsted acid catalyst. Sn(OH)Cl was synthesized by a precipitation method and characterized by XRD, FT-IR, 1H MAS NMR, SEM, TG-DTA and N2 sorption. The acidity measurements of tin(ii)hydroxychloride by FT-IR pyridine adsorption and 1H MAS NMR showed the presence of Bronsted acidity. The Bronsted acidity can be attributed to strong hydrogen bonding between the -OH and Cl groups. Sn(OH)Cl showed high activity for important condensation reactions such as the Prins condensation, Claisen-Schmidt condensation and ketalization. The catalytic activity of Sn(OH)Cl was compared with that of SnO, SnO2 and Sn2(OH)2O. The catalyst was recycled three times with a negligible decrease in activity. The Royal Society of Chemistry 2013.

Exploring the catalytic performance of a series of bimetallic MIL-100(Fe, Ni) MOFs

Giménez-Marqués, Mónica,Santiago-Portillo, Andrea,Navalón, Sergio,álvaro, Mercedes,Briois, Valérie,Nouar, Farid,Garcia, Hermenegildo,Serre, Christian

, p. 20285 - 20292 (2019)

A series of mixed-metal FeIII/NiII metal-organic frameworks (MOFs) of the MIL-100 type containing different metal ratios have been synthesized de novo, following an approach that requires tuning of the FeIII/NiII reactivity. The resulting heterometallic MIL-100(Fe, Ni) materials maintain thermal, chemical and structural stability with respect to the parent MIL-100(Fe) MOF as can be deduced from various techniques. The nature and the oxidation state of the accessible metal cations have been evaluated by in situ infrared spectroscopy and extended X-ray absorption fine structure measurements. The obtained mixed-metal MOFs and the parent material have been evaluated as heterogeneous catalysts in a model acid-catalyzed reaction, i.e., the Prins reaction. It is found that the catalytic activity improves by more than one order of magnitude upon incorporation of NiII, with a complete selectivity for the formation of nopol. This increase in the catalytic activity upon incorporation of NiII correlates with the enhancement in the Lewis acidity of the material as determined by CO adsorption. The heterometallic MOF can be recycled without observation of metal leaching, while maintaining the crystal structure under the reaction conditions.

Well ordered two-dimensional SnSBA-15 catalysts synthesized with high levels of tetrahedral tin for highly efficient and clean synthesis of nopol

Selvaraj,Choe

, p. 186 - 191 (2010)

Highly ordered two-dimensional SnSBA-15 molecular sieve catalysts with different concentrations of tin species have been synthesized using Pluronic P123 as a structure directing agent under pH-adjusting direct hydrothermal method and have been used for synthesis of nopol by Prins condensation of β-pinene with paraformaldehyde. The influence of various reaction parameters on this reaction has been investigated. The Prins condensation reaction has also been carried out with different solvents for finding the best solvent with a good catalytic activity. In addition, the Prins condensation of β-pinene with paraformaldehyde in the presence of propyl cyanide with water has been carried out for the synthesis of nopol, and in this condition the catalytic activity of the catalyst used was not seriously affected. On the basis of all catalytic results, SnSBA-15(5) is found to be a highly active, water-resistant and recyclable heterogeneous catalyst for selective synthesis of nopol.

Synthesis, antifungal activity and 3D-QSAR study of novel nopol-based 1,3,4-thiadiazole–thioether compounds

Wang, Xiu,Duan, Wen-Gui,Lin, Gui-Shan,Chen, Ming,Lei, Fu-Hou

, p. 4029 - 4049 (2021/06/21)

A series of novel nopol derivatives containing 1,3,4-thiadiazole–thioether moiety were synthesized from β-pinene, which is a natural, abundant and renewable biomass resource. Their structures were characterized by FT-IR, 1H NMR, 13C NMR, ESI–MS and elemental analysis. In vitro antifungal activity of the target compounds was preliminarily evaluated against eight tested plant pathogens, including Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis and Colleterichum orbicalare. The bioassay results revealed that, at the concentration of 50?μg/mL, all the target compounds showed certain inhibition activity against the eight tested fungi. Compounds 5f (R = m–OCH3), 5i (R = m–F) and 5r (R = m–I) had excellent inhibition rates of 77.8%, 88.9% and 77.8%, respectively, against P. piricola, showing much better antifungal activity than that of the positive control chlorothalonil. Meanwhile, compound 5?m (R = p–Cl) displayed antifungal activity of 80.7% against R. solani. Furthermore, the analysis of three-dimensional quantitative structure–activity relationship (3D-QSAR) was performed for the relationship between the structures of the target compounds and their antifungal activity against P. piricola by CoMFA method. A reasonable CoMFA model (n = 6; q2 = 0.597; r2 = 0.985) was established.

Design, synthesis and application of pinenyl chiral olefin and carbene ligand

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Paragraph 0031; 0035-0037, (2020/11/10)

The invention discloses design, synthesis and application of pinenyl chiral olefin and carbene ligands. According to the carbene ligand, pinene or 9-anthraceneformaldehyde is taken as a chiral source,a corresponding bromide is obtained through a two-step reaction, then benzimidazole is taken as an initial raw material, reacts with one molecule of bromide and then reacts with the other molecule ofbromide to form a salt, and corresponding pinenyl chiral olefin and carbene ligands are obtained; the carbene ligand is used as a chiral catalyst to perform asymmetric 1, 4-addition reaction, and hasfavorable selectivity.

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