7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid

Base Information

• Chemical Name: 7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid
• CAS No.: 263722-70-9
• Molecular Formula: C₁₆H₂₀N₂O₂
• Molecular Weight: 272.347
• Mol file: 263722-70-9.mol

Synonyms:7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid

Chemical Property of 7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid

There total 1 articles about 7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid 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: 95.0%

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) + phenylhydrazine (100-63-0) → 7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid (263722-70-9)

Guidance literature:

With acetic acid; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/ol990315n

Reference yield: 99.0%

7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid (263722-70-9) → 7,7-dimethyl-2'-phenyl-2',4'-dihydropyrazol-3'-one-bicyclo[2.2.1]heptane (263722-71-0)

Guidance literature:

With thionyl chloride; triethylamine; In ethyl acetate; at 60 ℃; for 5h;

DOI:10.1021/ol990315n

Reference yield:

7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid (263722-70-9) → (1S,5R,7R)-4-((S)-3-Hydroxy-2-methylene-pentanoyl)-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.01,5]decan-2-one

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / SOCl₂; Et₃N / ethyl acetate / 5 h / 60 °C

2: 94 percent / NaBH₄ / methanol / 1 h / 20 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 85 percent / DABCO / dimethylsulfoxide / 96 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; sodium tetrahydroborate; thionyl chloride; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1: Cyclization / 2: Reduction / 3: Acylation / 4: Baylis-Hillman reaction;

DOI:10.1021/ol990315n

upstream raw materials:

(1S)-(+)-ketopinic acid

phenylhydrazine

Downstream raw materials:

7,7-dimethyl-2'-phenyl-2',4'-dihydropyrazol-3'-one-bicyclo[2.2.1]heptane

7,7-dimethyl-2'-phenyl-pyrazol-3'-one-bicyclo[2.2.1]heptane

(1S,5R,7R)-4-Acryloyl-10,10-dimethyl-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one