Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-

Base Information

• Chemical Name: Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-
• CAS No.: 436146-73-5
• Molecular Formula: C15H14O
• Molecular Weight: 210.276
• DSSTox Substance ID: DTXSID60461239
• Nikkaji Number: J1.719.001F
• Wikidata: Q82285512
• Mol file: 436146-73-5.mol

Synonyms:Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-;436146-73-5;DTXSID60461239

Chemical Property of Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 210.104465066
• Heavy Atom Count: 16
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CC1=C(CCCC1)C(=O)C2=CC=CC=C2

Technology Process of Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-

There total 10 articles about Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl- 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: 52.0%

phenylmagnesium bromide + N-methyl N-methoxy 2-(trimethysilyl)-1-cyclohexenecarboxamide (439864-12-7) → (2-ethynylcyclohex-1-en-1-yl)(phenyl)methanone (436146-73-5)

Guidance literature:

phenylmagnesium bromide; N-methyl N-methoxy 2-(trimethysilyl)-1-cyclohexenecarboxamide; In tetrahydrofuran; at 20 ℃; for 4h;

With potassium hydroxide; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/S0022-328X(01)01328-6

Reference yield:

C18H22OSi → (2-ethynylcyclohex-1-en-1-yl)(phenyl)methanone (436146-73-5)

Guidance literature:

With potassium fluoride; In dimethyl sulfoxide; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol300718x

Reference yield:

2-((trimethylsilyl)ethynyl)cyclohex-1-ene-1-carbaldehyde (234111-16-1) → (2-ethynylcyclohex-1-en-1-yl)(phenyl)methanone (436146-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: potassium fluoride / dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere

With potassium fluoride; Dess-Martin periodane; magnesium; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ol300718x

upstream raw materials:

N-methyl N-methoxy 2-(trimethysilyl)-1-cyclohexenecarboxamide

bromobenzene

phenylmagnesium bromide

2-((trimethylsilyl)ethynyl)cyclohex-1-ene-1-carbaldehyde