Dimethyl cis-1,2,3,6-tetrahydrophthalate

Base Information

• Chemical Name: Dimethyl cis-1,2,3,6-tetrahydrophthalate
• CAS No.: 4841-84-3
• Molecular Formula: C10H14 O4
• Molecular Weight: 198.219
• Hs Code.: 2917399590
• DSSTox Substance ID: DTXSID90446413
• Nikkaji Number: J393.359H
• Wikidata: Q82265044
• Mol file: 4841-84-3.mol

Synonyms:4841-84-3;Dimethyl cis-1,2,3,6-tetrahydrophthalate;Dimethyl cis-4-Cyclohexene-1,2-dicarboxylate;cis-Dimethyl cyclohex-4-ene-1,2-dicarboxylate;dimethyl (1S,2R)-cyclohex-4-ene-1,2-dicarboxylate;1,2-DIMETHYL (1R,2S)-CYCLOHEX-4-ENE-1,2-DICARBOXYLATE;cis-4-Cyclohexene-1,2-dicarboxylic Acid Dimethyl Ester;SCHEMBL418068;dimethyl (1R,2S)-cyclohex-4-ene-1,2-dicarboxylate;DTXSID90446413;DVVAGRMJGUQHLI-OCAPTIKFSA-N;MFCD00209581;AS-66609;D90213;Dimethyl cis-1,2,3,6-tetrahydrophthalate, 99%;EN300-7394700;(1R,2S)-dimethyl cyclohex-4-ene-1,2-dicarboxylate;(1R, 6S)-Methyl 6-methoxycarbonyl-3-cyclohexenecarboxylate;4-Cyclohexene-1alpha,2alpha-dicarboxylic acid dimethyl ester

Chemical Property of Dimethyl cis-1,2,3,6-tetrahydrophthalate

Chemical Property:

• Vapor Pressure: 0.0137mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Boiling Point: 141-142 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 52.60000
• Density: 1.145 g/mL at 25 °C(lit.)
• LogP: 0.91480
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 198.08920892
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl cis-4-Cyclohexene-1,2-dicarboxylate >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1CC=CCC1C(=O)OC
• Isomeric SMILES: COC(=O)[C@@H]1CC=CC[C@@H]1C(=O)OC
• Uses: Dimethyl cis-1,2,3,6-tetrahydrophthalate may be used in chemical synthesis.

Technology Process of Dimethyl cis-1,2,3,6-tetrahydrophthalate

There total 13 articles about Dimethyl cis-1,2,3,6-tetrahydrophthalate 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: 97.0%

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3)

Guidance literature:

With sulfuric acid; In methanol; for 5h; Reflux;

DOI:10.1016/j.carres.2008.11.009

Reference yield: 96.0%

methanol (67-56-1) + cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3)

Guidance literature:

With sulfuric acid; Reflux; Inert atmosphere;

DOI:10.1002/anie.201411618

Reference yield: 88.0%

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) + trimethyl orthoformate (149-73-5) → dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3)

Guidance literature:

With Amberlyst 15; In methanol; at 20 ℃; for 216h;

DOI:10.1002/chem.201102884

upstream raw materials:

dimethyl cis-but-2-ene-1,4-dioate

buta-1,3-diene

methanol

cis-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

dimethyl cis-1,2-cyclohexanedicarboxylate

cis-4,5-diacetyl-cyclohexene

(+/-)-1-(cis-6-isopropenyl-cyclohex-3-enyl)-ethanone

(+/-)-4ξ-chloro-5ξ-hydroxy-cyclohexane-1r,2c-dicarboxylic acid dimethyl ester

Refernces

• 1、 Brazdova, Barbora,Tan, Nikmala S.,Samoshina, Nataliya M.,Samoshin, Vyacheslav V.. "Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids". . p. 311 - 321. Retrieved 2009.
• 2、 Michieletto, Ivan,Fabris, Fabrizio,De Lucchi, Ottorino. "Diastereoselective cis to trans desymmetrization of dimethyl succinates". . p. 2505 - 2509. Retrieved 1999.
• 3、 Fuchs, Michael,Fürstner, Alois. "Trans-hydrogenation: Application to a concise and scalable synthesis of brefeldin a". supporting information. p. 3978 - 3982. Retrieved 2015/03/30.