CONOCARPAN

Base Information

• Chemical Name: CONOCARPAN
• CAS No.: 221666-27-9
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.34
• Mol file: 221666-27-9.mol

Synonyms:Phenol,4-[(2S,3S)-2,3-dihydro-3-methyl-5-(1E)-1-propenyl-2-benzofuranyl]- (9CI)

Chemical Property of CONOCARPAN

Chemical Property:

• PSA: 29.46000
• LogP: 4.66250

Purity/Quality:

98%min ^*data from raw suppliers

Conocarpan ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CONOCARPAN

There total 38 articles about CONOCARPAN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(2R,3S)-3-methyl-5-[(E)-propen-1-yl]-2-(4-triisopropylsilyloxyphenyl)-2,3-dihydrobenzofuran (1158723-06-8) → (-)-epi-conocarpan (221666-27-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 23 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/jo900502d

Reference yield: 85.0%

(E)-1-(4-hydroxyphenyl)propene (20649-39-2) → (±)-conocarpan (221666-27-9)

Guidance literature:

With ammonium cerium (IV) nitrate; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tet.2012.11.006

Reference yield: 85.0%

2-(4-methoxyphenyl)-3-methyl-5-(1-propenyl)-cis-2,3-dihydrobenzofuran → (+/-)-epi-conocarpan (221666-27-9)

Guidance literature:

With n-butyllithium; diphenylphosphane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)02860-5

upstream raw materials:

toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester

toluene-4-sulfonic acid 4-[(R)-1-(4-formyl-2-iodophenoxy)allyl]phenyl ester

toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

(2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester

Downstream raw materials:

C₃₆H₃₆O₄

C₃₆H₃₆O₄

Refernces

• 1、 Silva, Allan R.,Polo, Ellen C.,Martins, Nelson C.,Correia, Carlos Roque D.. "Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan". . p. 346 - 365. Retrieved 2018/01/26.
• 2、 Chen, Cheng-Yi,Weisel, Mark. "Concise asymmetric synthesis of (+)-conocarpan and obtusafuran". . p. 189 - 192. Retrieved 2013/02/26.