(1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate

Base Information

• Chemical Name: (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate
• CAS No.: 186183-48-2
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.327
• Mol file: 186183-48-2.mol

Synonyms:

Chemical Property of (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate

There total 5 articles about (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate 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:

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) → (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate (186183-48-2)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂ / 3 h / 65 °C

2: aq. NH₃ / CH₂Cl₂ / 4 h / Ambient temperature

3: 51 percent / diethyl ether / 0 deg C, 5 min; room temperature, 90 min

4: p-toluenesulfonic acid / toluene / 24 h / Heating

5: various solvent(s) / Heating

With ammonium hydroxide; thionyl chloride; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; toluene;

DOI:10.1080/00397919608004785

Reference yield:

ketopinic acid chloride (54371-12-9,66884-33-1,66965-39-7,86023-72-5) → (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate (186183-48-2)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NH₃ / CH₂Cl₂ / 4 h / Ambient temperature

2: 51 percent / diethyl ether / 0 deg C, 5 min; room temperature, 90 min

3: p-toluenesulfonic acid / toluene / 24 h / Heating

4: various solvent(s) / Heating

With ammonium hydroxide; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; toluene;

DOI:10.1080/00397919608004785

Reference yield:

(1S)-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylamide-2-one (136087-99-5) → (1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carbonyl isocyanate (186183-48-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / diethyl ether / 0 deg C, 5 min; room temperature, 90 min

2: p-toluenesulfonic acid / toluene / 24 h / Heating

3: various solvent(s) / Heating

With toluene-4-sulfonic acid; In diethyl ether; toluene;

DOI:10.1080/00397919608004785

upstream raw materials:

oxalyl dichloride

(1S,4R)-7,7-Dimethyl-2-phenyl-bicyclo[2.2.1]hept-2-ene-1-carboxylic acid amide

(1S)-(+)-ketopinic acid

ketopinic acid chloride