Methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate

Base Information

Chemical Name:Methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate
CAS No.:131515-51-0
Molecular Formula:C₁₄H₁₃NO₂
Molecular Weight:227.263
Hs Code.:
DSSTox Substance ID:DTXSID301148189

Synonyms:131515-51-0;methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate;Bicyclo[1.1.1]pentane-1-carboxylic acid, 3-(3-cyanophenyl)-, methyl ester;DTXSID301148189;CID 14906684

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Chemical Property of Methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate

Chemical Property:

XLogP3:2
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:227.094628657
Heavy Atom Count:17
Complexity:386

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:COC(=O)C12CC(C1)(C2)C3=CC=CC(=C3)C#N

Technology Process of Methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate

There total 5 articles about Methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate 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:

: 83249-10-9
3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid

: 131515-51-0
methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / thionyl chloride / 1.5 h / Heating

2: 75 percent / methyllithium / tetrahydrofuran; diethyl ether; 2,2,4-trimethyl-pentane / 1 h / Ambient temperature

3: Heating

With thionyl chloride; methyllithium; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether;
DOI:10.1021/jo00001a058

Reference yield:

: methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[1.1.1]pentane-1-carboxylate

: 131515-51-0
methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: methanol; water / 3 h / 25 °C / Inert atmosphere

2: tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium carbonate / N,N-dimethyl acetamide; 1,4-dioxane / 20 h / Glovebox; Sealed tube; Inert atmosphere

With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; water; sodium carbonate; In 1,4-dioxane; N,N-dimethyl acetamide;
DOI:10.1021/acs.orglett.0c00242

Reference yield:

: 1-(1,3-dioxoisoindolin-2-yl) 3-methyl bicyclo[1.1.1]pentane-1,3-dicarboxylate

: 131515-51-0
methyl 3-(3-cyanophenyl)bicyclo[1.1.1]pentane-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: N,N-dimethyl acetamide / 0.58 h / 90 °C / Inert atmosphere; Irradiation

1.2: 25 °C / Inert atmosphere

2.1: methanol; water / 3 h / 25 °C / Inert atmosphere

3.1: tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium carbonate / N,N-dimethyl acetamide; 1,4-dioxane / 20 h / Glovebox; Sealed tube; Inert atmosphere

With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; water; sodium carbonate; In 1,4-dioxane; N,N-dimethyl acetamide;
DOI:10.1021/acs.orglett.0c00242