130092-20-5

Basic information

• Product Name: TRANS-4-CYCLOHEXYL-L-PROLINE
• Synonyms: DL-Proline,4-cyclohexyl-, trans-
• CAS NO: 130092-20-5
• Molecular Formula: C11H19NO2
• Molecular Weight: 197.27
• Mol File: 130092-20-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 343.919°C at 760 mmHg
• Flash Point: 161.797°C
• Appearance: /
• Density: 1.114g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: TRANS-4-CYCLOHEXYL-L-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-CYCLOHEXYL-L-PROLINE(130092-20-5)
• EPA Substance Registry System: TRANS-4-CYCLOHEXYL-L-PROLINE(130092-20-5)

Safety Data

• Hazardous Substances Data: 130092-20-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H19NO2/c13-11(14)10-6-9(7-12-10)8-4-2-1-3-5-8/h8-10,12H,1-7H2,(H,13,14)/t9-,10+/m1/s1

Upstream product

• 1521-51-3 rac-3-bromocyclohexene 
• 55629-96-4 ethyl 4-phenyl-2-oxobut-3-enoate 
• 103201-82-7 trans-4-cyclohexyl-L-prolinol 
• 394734-77-1 N-Boc-4-cyclohexyl-L-proline 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 88043-21-4 (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 103667-54-5 (R)-tetrahydro-3-phenyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one 
• 62400-75-3 pyroglutamol 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 78464-03-6 N-(benzyloxycarbonyl)-cis-4-hydroxy-trans-4-phenyl-L-proline 
• 82087-66-9 N-(benzyloxycarbonyl)-3,4-dehydro-4-phenyl-L-proline 
• 103290-40-0 cis-4-phenyl-L-proline 

Downstream Products

• 83624-20-8 (2S,4R)-4-Cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid 
• 95399-71-6 Fosinoprilat 

Relevant articles and documents

Preparation method of antihypertensive medicine key intermediate of trans-4-cyclohexyl-L-proline

The invention discloses a preparation method of trans-4-cyclohexyl-L-proline. The method comprises the following steps of (1) under the effect of an acid-binding agent, 4S-hydroxy-N-Boc-L-proline ester 6 and sulfonyl chloride are subjected to condensation to generate sulphonate 5, wherein R is C1-4 alkyl; (2) under the effects of a copper catalyst, lithium salt and organic alkali, the sulphonate 5and cyclohexylmagnesium bromide take nucleophilic substitution to generate a compound 4; (3) the compound 4 is hydrolyzed by lithium hydroxide to obtain (4S)-N-Boc-4-cyclohexyl-L-proline (a compound3); (4) the compound 3 is subjected to Boc removal under the condition of hydrochloric acid or trifluoroacetic acid/methylene dichloride; a target product 2 is prepared. The preparation method has thebeneficial effects that the target product structure and chirality are introduced through sulphonate and Grignard reagent nucleophilic substitution; the defects of the existing noble metal reductionmethod are overcome; the operation of the method is simple; the conditions are mild; the yield is good; the chemical purity and the optical purity are very high; the preparation method is suitable forindustrial production.

A practical synthesis of optically active δ-nitro-α-ketoesters and 4-cyclohexyl-proline catalyzed by chiral squamides

Inexpensive and readily available squamides derived from 9-amino-9-deoxyepiquinine or 9-amino-9-deoxyepiquinidine were found to be superior catalysts for the asymmetric conjugate additions of t-butyl nitroacetate to β,γ-unsaturated-α-ketoesters. After the subsequent decarboxylation with silica gel, a variety of δ-nitro-α-ketoesters were obtained in good yields and with excellent enantioselectivities. The products were further transformed into ethyl 4-aryl-prolinate via a cascade nitro reduction and amination. A new synthesis of (2S,4S)-4-cyclohexyl-proline was also developed. A practical synthesis of optically active δ-nitro-α-ketoesters and 4-aryl-proline derivatives is described.

Process for preparing (trans)-4-substituted-dl-proline derivatives

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