3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one

Base Information

• Chemical Name: 3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one
• CAS No.: 112014-67-2
• Molecular Formula: C₁₆H₁₈O₃
• Molecular Weight: 258.317
• Mol file: 112014-67-2.mol

Synonyms:

Chemical Property of 3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one

There total 8 articles about 3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one 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: 78.0%

(+/-)-3-endo-hydroxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one (100853-07-4,100898-04-2,112067-69-3,112067-70-6,132201-55-9) + benzoic acid (65-85-0,8013-63-6) → 3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one (112014-67-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;

Reference yield:

(+/-)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one (767-85-1,100853-05-2,100898-02-0,100898-03-1) → Benzoic acid (1S,3R,5R)-6,6-dimethyl-7-oxo-bicyclo[3.2.0]hept-3-yl ester (112014-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 22 percent / 3α,20β-hydroxy-steroid dehydrogenase, NAD(1+), 200 mM Tris-HCl buffer, glycerol, glucose, MnSO4, glucose dehydrogenase / 24 h

2: 65 percent / pyridinium chlorochromate

3: 1.) MeCONHBr, H₂O / 1.) acetone, 22 h, RT; 2.) light petroleum, -10 deg C, overnight

4: Bu₃SnH / AIBN / toluene / 0.5 h / Ambient temperature

5: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

With glucose dehydrogenase; manganese(II) sulfate; Tris-HCl buffer; D-glucose; 3α,20β-hydroxy-steroid dehydrogenase; water; tri-n-butyl-tin hydride; nicotinamide adenine dinucleotide; triphenylphosphine; glycerol; pyridinium chlorochromate; diethylazodicarboxylate; N-bromoacetamide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; toluene;

Reference yield:

(+/-)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one (767-85-1,100853-05-2,100898-02-0,100898-03-1) → 3-exo-benzoyloxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one (112014-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) MeCONHBr, H₂O / 1.) acetone, 22 h, RT; 2.) light petroleum, -10 deg C, overnight

2: 82 percent / Bu₃SnH / AIBN / toluene / 0.5 h / Ambient temperature

3: 78 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

With water; tri-n-butyl-tin hydride; triphenylphosphine; diethylazodicarboxylate; N-bromoacetamide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; toluene;

upstream raw materials:

(1R,3S,5S)-3-hydroxy-7,7-dimethylbicyclo<3.2.0>heptan-6-one

benzoic acid

(+/-)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one

(1R,5S,6S)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-endo-ol

Refernces