1-Cycloheptene-1-carboxaldehyde, 2-(phenylethynyl)-

Base Information

• Chemical Name: 1-Cycloheptene-1-carboxaldehyde, 2-(phenylethynyl)-
• CAS No.: 106180-32-9
• Molecular Formula: C16H16O
• Molecular Weight: 224.302
• DSSTox Substance ID: DTXSID90457983
• Nikkaji Number: J2.068.905F
• Mol file: 106180-32-9.mol

Synonyms:1-Cycloheptene-1-carboxaldehyde, 2-(phenylethynyl)-;106180-32-9;DTXSID90457983;2-(Phenylethynyl)-1-cycloheptene-1-carbaldehyde

Chemical Property of 1-Cycloheptene-1-carboxaldehyde, 2-(phenylethynyl)-

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 224.120115130
• Heavy Atom Count: 17
• Complexity: 358

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=C(CC1)C#CC2=CC=CC=C2)C=O

Technology Process of 1-Cycloheptene-1-carboxaldehyde, 2-(phenylethynyl)-

There total 7 articles about 1-Cycloheptene-1-carboxaldehyde, 2-(phenylethynyl)- 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: 73.0%

2-bromocyclohept-1-ene-1-carbaldehyde (85236-13-1) + phenylacetylene (536-74-3) → 2-Phenylethynyl-cyclohept-1-enecarbaldehyde (106180-32-9)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01393-2

Reference yield:

cycloheptanone (502-42-1) → 2-Phenylethynyl-cyclohept-1-enecarbaldehyde (106180-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / PBr₃ / CHCl₃

2: 73 percent / CuI, NEt₃ / Pd(PPh₃)4 / dimethylformamide

With copper(l) iodide; phosphorus tribromide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01393-2

Reference yield:

2-[1-Isopropoxy-meth-(Z)-ylidene]-1-phenylethynyl-cycloheptanol (106180-71-6) → 2-Phenylethynyl-cyclohept-1-enecarbaldehyde (106180-32-9)

Guidance literature:

With sulfuric acid; In ethanol; for 3h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)90602-7

upstream raw materials:

2-[1-Isopropoxy-meth-(Z)-ylidene]-1-phenylethynyl-cycloheptanol

2-bromocyclohept-1-ene-1-carbaldehyde

phenylacetylene

cycloheptanone

Downstream raw materials:

3-Phenyl-1-(2-phenylethynyl-cyclohept-1-enyl)-prop-2-yn-1-ol

C₁₆H₁₆O₂

1-(2-Phenylethynyl-cyclohept-1-enyl)-hept-2-yn-1-ol

(E)-3-<2-(2-Phenylethynyl)-1-cycloheptenyl>-oxirane-2-carbonitrile