Dimethyl (1S,2S)-3,3-dimethylcyclopropane-1,2-dicarboxylate

Base Information

• Chemical Name: Dimethyl (1S,2S)-3,3-dimethylcyclopropane-1,2-dicarboxylate
• CAS No.: 16601-23-3
• Molecular Formula: C9H14O4
• Molecular Weight: 186.208
• DSSTox Substance ID: DTXSID00512678
• Nikkaji Number: J2.599.036F
• Wikidata: Q82372031
• Mol file: 16601-23-3.mol

Synonyms:16601-23-3;SCHEMBL2690901;JVZYMEXLQMHFCI-PHDIDXHHSA-;DTXSID00512678;JVZYMEXLQMHFCI-PHDIDXHHSA-N;Dimethyl (1S,2S)-3,3-dimethylcyclopropane-1,2-dicarboxylate;Dimethyl 3,3-dimethyl-1,2-cyclopropanedicarboxylate #;(-)-Methyl-3,3-dimethylcyclopropane-1,trans-2-dicarboxylate;InChI=1/C9H14O4/c1-9(2)5(7(10)12-3)6(9)8(11)13-4/h5-6H,1-4H3/t5-,6-/m1/s1

Chemical Property of Dimethyl (1S,2S)-3,3-dimethylcyclopropane-1,2-dicarboxylate

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 186.08920892
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C1C(=O)OC)C(=O)OC)C
• Isomeric SMILES: CC1([C@H]([C@@H]1C(=O)OC)C(=O)OC)C

Technology Process of Dimethyl (1S,2S)-3,3-dimethylcyclopropane-1,2-dicarboxylate

There total 3 articles about Dimethyl (1S,2S)-3,3-dimethylcyclopropane-1,2-dicarboxylate 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:

2,2-dichloropropane (594-20-7) + dimethylfumarate (624-49-7) → dimethyl trans-3,3-dimethylxyclopropane-1,2-dicarboxylate (16601-23-3) + 2-isopropenylbutanedioic acid 1,4-dimethyl ester (87384-00-7) + Dimethyl succinate (106-65-0)

Guidance literature:

With cobalt chloride; sodium iodide; zinc; Yield given. Yields of byproduct given; 1.) acetonitrile, RT, 2.) acetonitrile, RT, 64 h;

DOI:10.1246/bcsj.56.1592

Reference yield:

2,2-dibromopropane (594-16-1) + dimethylfumarate (624-49-7) → dimethyl trans-3,3-dimethylxyclopropane-1,2-dicarboxylate (16601-23-3) + 2-isopropenylbutanedioic acid 1,4-dimethyl ester (87384-00-7) + Dimethyl succinate (106-65-0)

Guidance literature:

With sodium iodide; nickel dibromide; zinc; Yield given. Yields of byproduct given; 1.) acetonitrile, RT, 2.) acetonitrile, RT, 27 h;

DOI:10.1246/bcsj.56.1592

Reference yield:

2,2-dibromopropane (594-16-1) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → Dimethyl meso-3,3-Dimethylcyclopropane-1,2-dicarboxylate (20315-30-4) + dimethyl trans-3,3-dimethylxyclopropane-1,2-dicarboxylate (16601-23-3) + 2-isopropenylbutanedioic acid 1,4-dimethyl ester (87384-00-7) + Dimethyl succinate (106-65-0)

Guidance literature:

With sodium iodide; nickel dibromide; zinc; Yield given. Yields of byproduct given; 1.) acetonitrile, RT, 2.) acetonitrile, RT, 27 h;

DOI:10.1246/bcsj.56.1592

upstream raw materials:

2,2-dibromopropane

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

2,2-dichloropropane

dimethylfumarate