141540-20-7

Basic information

• Product Name: Acetic acid, (diethoxyphosphinyl)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester
• CAS NO: 141540-20-7
• Molecular Formula: C16H31O5P
• Molecular Weight: 334.393
• Mol File: 141540-20-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Acetic acid, (diethoxyphosphinyl)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, (diethoxyphosphinyl)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(141540-20-7)
• EPA Substance Registry System: Acetic acid, (diethoxyphosphinyl)-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester(141540-20-7)

Safety Data

• Hazardous Substances Data: 141540-20-7(Hazardous Substances Data)

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 2216-51-5 (-)-menthol 
• 3095-95-2 diethylphosphonoacetic acid 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 
• 122-52-1 triethyl phosphite 

Downstream Products

• 1420377-65-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2R,4S)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 1420377-68-9 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2R)-1-(diethoxyphosphoryl)-2-methylcyclohex-3-ene-1-carboxylate 
• 1542432-75-6 (2E,4E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-5-phenylpenta-2,4-dienoate 
• 1542432-73-4 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate 
• 1420376-95-9 3,5-dinitro-benzoic acid 2-(diethoxy-phosphoryl)-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 1420376-92-6 3,5-dinitro-benzoic acid 1-(diethoxy-phosphoryl)-2-methyl-cyclohex-3-enylmethyl ester 
• 1420376-77-7 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2S,4R)-2-(diethoxyphosphoryl)bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 1420376-83-5 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1S,2S)-1-(diethoxyphosphoryl)-2-methylcyclohex-3-enecarboxylate 
• 1420376-59-5 2-(diethoxy-phosphoryl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 2216-51-5 (-)-menthol 
• 1420376-89-1 (2-formyl-bicyclo[2.2.1]hept-5-en-2-yl)-phosphonic acid diethyl ester 

Relevant articles and documents

A selective C-H insertion/olefination protocol for the synthesis of α-methylene-γ-butyrolactone natural products

A regio- and stereoselective one-pot C-H insertion/olefination protocol has been developed for the late stage installation of α-methylene-γ-butyrolactones into conformationally restricted cyclohexanol-derivatives. The method has been successfully applied in the total synthesis of eudesmanolide natural product frameworks, including α-cyclocostunolide.

Lewis acid mediated asymmetric Diels-Alder reactions of chiral 2-phosphonoacrylates

2-Phosphonoacrylates containing four chiral alcohol auxiliaries were efficiently prepared and evaluated in Lewis acid mediated Diels-Alder reactions. Under the activation of SnCl4, all reactions performed in CH 2Cl2 at -65 °C exclusively afforded the endo (endo-to-carboxylate) cycloadducts with dr's ranging from 50:50 to >99:1. The best facial selectivity was obtained from the substrate bearing a (-)-phenylmenthyl group, to give adducts as (dr >99:1) or almost as (dr = 99:1) single diastereomers. Detailed strategies for the structural elucidation of the cycloadducts as well as a rationalization of the observed stereoselectivity are described.

Stereochemical considerations on the stereoselective cyclopropanation reactions of 3-aryl-2-phosphonoacrylates induced by the (-)-8-phenylmenthyl group as a chiral auxiliary

The cyclopropanation of (-)-8-phenylmenthyl (E)-3-aryl-2-phosphonoacrylates E-3a-d with dimethyloxosulfonium methylide and diazomethane affords the corresponding trans cyclopropane derivatives as the major diastereomers with high diastereoselectivity. On