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Cas Database

80868-49-1

80868-49-1

Identification

  • Product Name:(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

  • CAS Number: 80868-49-1

  • EINECS:

  • Molecular Weight:352.517

  • Molecular Formula: C24H32O2

  • HS Code:

  • Mol File:80868-49-1.mol

Synonyms:

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Relevant articles and documentsAll total 6 Articles be found

Mixed-Ligand Arenechromium Carbonyl Complexes as Electronic Modulators

Jones, Graham B.,Chapman, Brant J.,Mathews, Jude E.

, p. 2928 - 2938 (1998)

A number of mixed ligand η6 arenechromium carbonyl complexes have been prepared and investigated for their ability to effect electronic modulation of arene chemistry. In the case of an aniline-derived system, the arenechromium carbonyl complex is able to modulate the inductive capacity of the aniline nitrogen atom and thus, regulate its anchimeric ability. In the case of 8-phenylmenthol and benzyloxazolidinone derivatives, modulation of arene π basicity is achieved, and results suggest that important vinylarene π-π interactions exist in acrylate derivatives of these chiral auxiliary systems.

AlPO4-Catalysed Asymmetric Diels-Alder Reactions of Cyclopentadiene with Chiral Acrylates

Cativiela, Carlos,Fraile, Jose M.,Garcia, Jose I.,Mayoral, Jose A.,Campelo, Juan M.,et al.

, p. 2507 - 2512 (2007/10/02)

Reactions of cyclopentadiene with several chiral acrylates are studied and compared with the same reactions catalysed by Zn(II)-exchanged K10 montmorillonite.In general, amorphous AlPO4 is a more efficient catalyst than the clay.In particular, the reaction of cyclopentadiene with (-)-8-phenylmenthyl acrylate leads to 74percent diastereomeric excess (d.e.) in methylene chloride at low temperatures.This result constitutes the highest asymmetric induction described to date for solid-catalysed asymmetric Diels-Alder reaction.When the reactions are carried out in the absence of a solvent a noticeable decrease in selectivity is observed, probably due to an extensive competition of non-catalysed reaction.

Fluorinated alcohols as solvents for Diels-Alder reactions of chiral acrylates

Cativiela,Garcia,Mayoral,Royo,Salvatella

, p. 1613 - 1618 (2007/10/02)

Fluorinated alcohols increase the rates of endo/exo selectivities of the Diels-Alder reactions of cyclopentadiene with (-)-menthyl and (-)-8-phenylmenthyl acrylates. The use of fluorinated alcohols also increases the diastereofacial selectivity in the reactions of (-)-menthyl acrylate, but decreases it when the dienophile is (-)-8-phenylmenthyl acrylate. These facts are accounted for by the conformational preferences of the dienophile in non-HBD solvents and by the tendency of fluorinated alcohols to shift the conformational equilibrium towards the s-trans conformation.

Asymmetric syntheses with a new optically active perhydronaphthalene based chiral auxiliary

Hamon,Holman,Massy-Westropp

, p. 9593 - 9604 (2007/10/02)

(1R,4aS,8S,8aS)-8-(5'-Methoxy-2'-methylphenyl)-8-methyldecahydro-1-nap hthalenol 3a is a highly efficient chiral auxiliary in the Diels-Alder addition of its acrylate ester 5 and in the DIBAL-H and Grignard reactions of its phenylglyoxylate ester 7.

Preparation of 8-Phenylmenthol and Its Diastereomer, 2-epi,ent-8-Phenylmenthol. A Caveat

Whitesell, James K.,Liu, Chi-Ling,Buchanan, Charles M.,Chen, Hwang-Hsing,Minton, Mark A.

, p. 551 - 553 (2007/10/02)

-

Process route upstream and downstream products

Process route

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate
80868-49-1,100101-46-0

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 91 percent / Et3N / CH2Cl2 / -10 - 25 °C
2: 97 percent / BF3*Et2O / CH2Cl2 / 4 h / 0 °C
With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; 1: Esterification / 2: Cyclization;
(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate
80868-49-1,100101-46-0

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions
Conditions Yield
With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 4h;
97%
(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol
100101-42-6

(1S,2R,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexanol

(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
80868-49-1,100101-46-0

(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 91 percent / 4-(dimethylamino)pyridine, triethylamine / CH2Cl2 / 1.5 h / 0 °C
2: 1.) titanium tetrachloride / 1.) dichloromethane, 0 deg C, 45 min, 2.) 4 h
With dmap; titanium tetrachloride; triethylamine; In dichloromethane;
(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
80868-49-1

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
155898-96-7

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

Conditions
Conditions Yield
With titanium tetrachloride; In dichloromethane; at 0 ℃; Product distribution; 1.) 45 min, 2.) 5 h;
With titanium tetrachloride; Multistep reaction; 1.) dichloromethane, 0 deg C, 45 min, 2.) 4 h;
With titanium tetrachloride; In dichloromethane; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 1.) 45 min, 2.) 5 h;
cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

(1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate
100020-75-5

(1S,2R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl acrylate

(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
80868-49-1,100101-46-0

(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate
100101-46-0

(1S,2R,5R,2'S)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl endo-2-bicyclo<2.2.1>heptanecarboxylate

Conditions
Conditions Yield
With titanium tetrachloride; Multistep reaction. Yields of byproduct given; 1.) dichloromethane, 0 deg C, 45 min, 2.) 4 h;
With titanium tetrachloride; Yield given. Multistep reaction; 1.) dichloromethane, 0 deg C, 45 min, 2.) 4 h;
(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate
80868-49-1,100101-46-0

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
80868-49-1

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
155898-96-7

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

Conditions
Conditions Yield
With titanium tetrachloride; In toluene; at -20 ℃; for 3.5h; Product distribution; variation of Lewis acid, solvent, temperature, reaction time;
titanium tetrachloride; In toluene; at -20 ℃; for 3.5h; Yield given. Yields of byproduct given;
aluminium trichloride; In toluene; at -20 ℃; for 3.5h; Yield given. Yields of byproduct given;
(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate
80868-49-1,100101-46-0

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
80868-49-1

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
155898-96-7

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

Conditions
Conditions Yield
With titanium tetrachloride; In toluene; at -20 ℃; for 3.5h; Product distribution; variation of Lewis acid, solvent, temperature, reaction time;
titanium tetrachloride; In toluene; at -20 ℃; for 3.5h; Yield given. Yields of byproduct given;
aluminium trichloride; In toluene; at -20 ℃; for 3.5h; Yield given. Yields of byproduct given;
(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
80868-49-1

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate
155898-96-7

(1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (S)-endo-2-bicyclo<2.2.1>hept-5-enecarboxylate

(1S,2R,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(1S,2R,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(1R,2S,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(1R,2S,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Conditions
Conditions Yield
monoaluminum phosphate; In dichloromethane; at 20 ℃; for 16h; Product distribution; sev. chiral acrylates, other cat., other temp.; asymmetric Diels-Alder reactions;
With ethylaluminum dichloride; In dichloromethane; at 0 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
In methanol; water; for 120h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate
80868-49-1,100101-46-0

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 91 percent / Et3N / CH2Cl2 / -10 - 25 °C
2: 97 percent / BF3*Et2O / CH2Cl2 / 4 h / 0 °C
With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; 1: Esterification / 2: Cyclization;
(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate
80868-49-1,100101-46-0

5-methyl-2-(1-methyl-1-phenylethyl)cyclohexylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions
Conditions Yield
With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 4h;
97%

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