BICYCLO[2,21]HEPTANE-2,3-DICARBOXYLIC ACID MONOMETHYL ESTER

Base Information

• Chemical Name: BICYCLO[2,21]HEPTANE-2,3-DICARBOXYLIC ACID MONOMETHYL ESTER
• CAS No.: 76232-01-4
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Hs Code.: 2918990090
• Mol file: 76232-01-4.mol

Synonyms:Bicyclo[2.2.1]heptane-2,3-dicarboxylicacid, monomethyl ester (9CI)

Chemical Property of BICYCLO[2,21]HEPTANE-2,3-DICARBOXYLIC ACID MONOMETHYL ESTER

Chemical Property:

• Vapor Pressure: 5.27E-05mmHg at 25°C
• Refractive Index: 1.523
• Boiling Point: 323.6°C at 760 mmHg
• Flash Point: 127.2°C
• PSA: 63.60000
• Density: 1.278g/cm³
• LogP: 0.90630

Purity/Quality:

99% ^*data from raw suppliers

3-(Methoxycarbonyl)bicyclo[2.2.1]heptane-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BICYCLO[2,21]HEPTANE-2,3-DICARBOXYLIC ACID MONOMETHYL ESTER

There total 20 articles about BICYCLO[2,21]HEPTANE-2,3-DICARBOXYLIC ACID MONOMETHYL ESTER 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: 93.0%

methanol (67-56-1) + exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (14166-28-0) → (1R,2S,3R,4S)-2-(Methoxycarbonyl)bicyclo<2.2.1>heptane-3-carboxylic Acid (14253-59-9,55298-06-1,76232-01-4,116404-48-9,125226-86-0,128298-84-0,128441-83-8,130464-54-9,132747-52-5,135357-73-2)

Guidance literature:

With 4-((4-((1S)-hydroxy((2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-yl)oxy)butanoic acid modified Fe₃O₄ nanoparticles; In diethyl ether; at -45 ℃; for 60h; enantioselective reaction; Inert atmosphere;

DOI:10.1039/d1nj04081b

Reference yield:

dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1) → (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid (14253-59-9,55298-06-1,76232-01-4,116404-48-9,125226-86-0,128298-84-0,128441-83-8,130464-54-9,132747-52-5,135357-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 3 h / Ambient temperature; pig liver esterase (PLE), phosphate buffer, pH 7.8

2: H₂ / Pd/C / ethyl acetate

With hydrogen; palladium on activated charcoal; In ethyl acetate;

Reference yield:

D,L-1-[N-(3-Methoxycarbonyl-5-norbornen-2-yl)carbamoyl]-5-fluorouracil (76197-79-0) → bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester (36897-94-6) + 3-(methoxycarbonyl)bicyclo<2.2.1>heptane-2-carboxylic acid (76232-01-4)

Guidance literature:

palladium charcoal; In ethanol;

upstream raw materials:

(1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-((R)-methoxycarbonyl-phenyl-methyl) ester 3-methyl ester

(1R,2S,3R,4S)-2-<(R)-Mandeloxycarbonyl>-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid

norcantharidin

methanol

Refernces

• 1、 Wang, Peng,Li, Gen-Cheng,Jain, Pankaj,Farmer, Marcus E.,He, Jian,Shen, Peng-Xiang,Yu, Jin-Quan. "Ligand-Promoted meta-C-H Amination and Alkynylation". . p. 14092 - 14099. Retrieved 2016/11/06.
• 2、 Ohtani, Mitsuaki,Matsuura, Takaharu,Watanabe, Fumihiko,Narisada, Masayuki. "Highly Effective and Practical Enantioselective Synthesis of Half-Esters of Bicycloheptanedicarboxylic Acid". . p. 4120 - 4123. Retrieved 2007/10/02.