(1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide

Base Information

• Chemical Name: (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide
• CAS No.: 162089-64-7
• Molecular Formula: C₁₆H₂₂Cl₃NO₃
• Molecular Weight: 382.715
• Mol file: 162089-64-7.mol

Synonyms:(1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide

Chemical Property of (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide

There total 5 articles about (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]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:

2,2,2-Trichloro-acetimidic acid 2-[(S)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-cyclohex-3-en-(Z)-ylidene]-ethyl ester (199801-72-4) → (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide (162089-64-7)

Guidance literature:

In xylene; Yield given; Heating;

DOI:10.1246/cl.1994.2299

Reference yield:

2-[(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-methyl-cyclohex-3-en-(Z)-ylidene]-ethanol (162089-63-6) → (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide (162089-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / -35 °C

2: 27.4 g / potassium carbonate / p-xylene / 20 h / Heating

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

DOI:10.1016/S0040-4020(01)00258-7

Reference yield:

(S)-1-{(S)-6-[2-Hydroxy-eth-(Z)-ylidene]-3-methyl-cyclohex-3-enyl}-ethane-1,2-diol → (1S,6S,1'S)-trichloro-N-[1-vinyl-4-methyl-6-(3',3'-dimethyl-2',4'-dioxolanyl)-cyclohex-3-enyl]acetamide (162089-64-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 11.8 g / DL-camphorsulfonic acid / acetone / 0.25 h / 20 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / -35 °C

3: 27.4 g / potassium carbonate / p-xylene / 20 h / Heating

With camphor-10-sulfonic acid; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; para-xylene; acetone; 3: Overman rearrangement;

DOI:10.1016/S0040-4020(01)00258-7

upstream raw materials:

2,2,2-Trichloro-acetimidic acid 2-[(S)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-cyclohex-3-en-(Z)-ylidene]-ethyl ester

2-[(S)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-methyl-cyclohex-3-en-(Z)-ylidene]-ethanol

Acetic acid (1S,8aS)-3-hydroxy-7-methyl-3,5,8,8a-tetrahydro-1H-isochromen-1-ylmethyl ester

Downstream raw materials:

2,2,2-Trichloro-N-[(1R,2S,4S,5S)-4,5-dibromo-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-1-vinyl-cyclohexyl]-acetamide

N,N'-Dibenzyl-N''-[(1R,6S)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-1-vinyl-cyclohex-3-enyl]-guanidine

Benzoic acid (1R,2S,4S,5S)-5-(3-benzyl-ureido)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-ethyl-2-hydroxy-2-methyl-cyclohexyl ester

Benzoic acid (1R,2S,4S,5R)-5-(3-benzyl-ureido)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-2-methyl-5-vinyl-cyclohexyl ester