2,2,2-Trichloro-N-(2-phenylbut-3-en-2-yl)acetamide

Base Information

• Chemical Name: 2,2,2-Trichloro-N-(2-phenylbut-3-en-2-yl)acetamide
• CAS No.: 138313-58-3
• Molecular Formula: C12H12Cl3NO
• Molecular Weight: 292.592
• DSSTox Substance ID: DTXSID70579056
• Nikkaji Number: J1.295.789K
• Mol file: 138313-58-3.mol

Synonyms:138313-58-3;2,2,2-Trichloro-N-(2-phenylbut-3-en-2-yl)acetamide;SCHEMBL13655731;DTXSID70579056

Chemical Property of 2,2,2-Trichloro-N-(2-phenylbut-3-en-2-yl)acetamide

Chemical Property:

• PSA: 32.59000
• LogP: 4.41450
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 290.998447
• Heavy Atom Count: 17
• Complexity: 295

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=C)(C1=CC=CC=C1)NC(=O)C(Cl)(Cl)Cl

Technology Process of 2,2,2-Trichloro-N-(2-phenylbut-3-en-2-yl)acetamide

There total 5 articles about 2,2,2-Trichloro-N-(2-phenylbut-3-en-2-yl)acetamide 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: 60.0%

2,2,2-Trichlorethanimidsaeure-O-(3-phenyl-2-butenyl)ester (138313-57-2) → 2,2,2-Trichlor-N-(2-phenyl-3-buten-2-yl)ethensaeureamid (138313-58-3)

Guidance literature:

With sodium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h; enantioselective reaction; Reflux;

DOI:10.1002/ejoc.201601446

Reference yield:

(E)-3-phenylbut-2-enyl 2,2,2-trichloroethanimidoate (273377-11-0) → 2,2,2-Trichlor-N-(2-phenyl-3-buten-2-yl)ethensaeureamid (138313-58-3)

Guidance literature:

In xylene; Heating;

DOI:10.1016/S0040-4039(99)01768-2

Reference yield:

(E)-3-phenylbut-2-en-1-ol (54976-38-4) → 2,2,2-Trichlor-N-(2-phenyl-3-buten-2-yl)ethensaeureamid (138313-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 1 h / -10 °C

2: Na₂CO₃ / xylene / 24 h / Heating

With sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; xylene; 1: Substitution / 2: Overman rearrangement;

DOI:10.1080/00397910008087201

upstream raw materials:

2,2,2-Trichlorethanimidsaeure-O-(3-phenyl-2-butenyl)ester

(E)-3-phenylbut-2-enyl 2,2,2-trichloroethanimidoate

(E)-3-phenylbut-2-en-1-ol

ethyl 3-phenylbut-2-enoate

Downstream raw materials:

2-Phenyl-3-buten-2-ylamin

tert-butyl 1-methyl-1-phenylprop-2-enylcarbamate

2-phenyl-1,3-butadiene

2-methyl-2-phenyl-3-butenenitrile