349078-99-5

Basic information

• Product Name: (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-en-1-ol
• Synonyms: (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-en-1-ol
• CAS NO: 349078-99-5
• Molecular Weight: 292.419
• Mol File: 349078-99-5.mol

Chemical Properties

• CAS DataBase Reference: (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-en-1-ol(349078-99-5)
• EPA Substance Registry System: (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-en-1-ol(349078-99-5)

Safety Data

• Hazardous Substances Data: 349078-99-5(Hazardous Substances Data)

Upstream product

• 349078-95-1 (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-enoic acid 
• 349078-78-0 Acetic acid (Z)-(R)-3-(3,4-dimethoxy-phenyl)-1,4-dimethyl-pent-2-enyl ester 
• 349078-89-3 (4E,3R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enol 
• 349078-97-3 methyl (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-enoate 
• 349078-91-7 (4E,3R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enyl tosylate 
• 349078-93-9 (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-enenitrile 
• 349078-87-1 methyl (4E,3R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoate 
• 349078-84-8 (E,R)-(-)-3-(3,4-dimethoxyphenyl)-3-isopropylhex-4-enoic acid 

Downstream Products

• 349079-03-4 (4S)-(-)-4-(3,4-dimethoxyphenyl)-4-formyl-5-methylhexyl acetate 
• 255721-21-2 (4S)-(-)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl acetate 
• 38176-01-1 (2R)-(+)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile 
• 36622-26-1 (2S)-(-)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile 
• 36622-29-4 (S)-verapamil 
• 36770-70-4 (2R)-(+)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile 
• 36770-70-4 (2S)-(-)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile 
• 38321-02-7 dexverapamil 
• 349079-01-2 (5E,4R)-(-)-4-(3,4-dimethoxyphenyl)-4-isopropylhept-5-enyl acetate 

Relevant articles and documents

Synthesis of the Verapamil Intermediate through the Quaternary Carbon-Constructing Allylic Substitution

In the present study, the key secondary allylic picolinate was synthesized via Pd(PPh 3) 4 -catalyzed coupling of the TBS ether of (R, Z)-4-iodo-5-methylhex-3-en-2-ol with allyl-MgBr. Allylic substitution of the picolinate with the copper reagent derived from 3,4-(MeO) 2 C 6 H 3 MgBr and Cu(acac) 2 in a 2:1 ratio afforded the anti S N 2′ product with complete chirality transfer and 91% regioselectivity. Synthetic manipulation of the olefin moiety led to the nitrile group, generating the intermediate for the synthesis of (S)-verapamil.

Enzyme-mediated synthesis of (S)- And (R)-verapamil

A lipase-mediated synthesis of (S)- And (R)-verapamil is described. The key steps of the synthetic sequence are the enantioselective acetylation, mediated by Lipase PS, of allylic alcohol (Z)-(±)-2, affording the acetate derivative (Z,R)-(-)-3 (ee 92%) and the Ireland-Claisen rearrangement of this latter and of its enantiomer (Z,S)-(+)-3 (ee 92%) to afford acid derivatives (E,R)-(-)-4 (ee 94%) and (E,S)-(+)-4 (ee 93%), precursors of (S)- and (R)-verapamil, respectively.