(1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester
• CAS No.: 503167-42-8
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.191
• Mol file: 503167-42-8.mol

Synonyms:(1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property of (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester

There total 4 articles about (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester 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:

dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3) → (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester (503167-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 3 h / 30 °C / pig liver esterase (PLE), pH 8.0 phosphate buffer-10 percent acetone

2: Et₃N

3: NaN₃

4: Heating

With sodium azide; triethylamine;

DOI:10.1016/S0040-4039(00)98938-X

Reference yield:

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester (503167-42-8)

Guidance literature:

Multi-step reaction with 2 steps

1: quinindine

2: diphenyl phosphoryl azide; triethylamine / toluene / 80 °C / Inert atmosphere; Reflux

With diphenyl phosphoryl azide; quinindine; triethylamine; In toluene; 1: B?lm desymmetrization / 2: Curtius rearrangement;

DOI:10.1016/j.tet.2011.05.131

Reference yield:

(1S,6R)-6-Azidocarbonyl-cyclohex-3-enecarboxylic acid methyl ester → (1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester (503167-42-8)

Guidance literature:

In benzene; for 2h; Heating;

DOI:10.1248/cpb.38.350

upstream raw materials:

dimethyl cis-1,2,3,6-tetrahydrophthalate

cis-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

(1S,6R)-6-Benzyloxycarbonylamino-cyclohex-3-ene-1-carboxylic acid methyl ester

(1S,6R)-6-Amino-cyclohex-3-enecarboxylic acid methyl ester

(1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

(1S,6R)-6-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionylamino)-cyclohex-3-enecarboxylic acid methyl ester