5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Base Information

• Chemical Name: 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
• CAS No.: 866129-89-7
• Molecular Formula: C₂₅H₃₃NO₇
• Molecular Weight: 459.54

Synonyms:5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Chemical Property of 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

There total 9 articles about 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane 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: 82.8%

4-tert-butyl-5-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran (866129-88-6) → 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (866129-89-7)

Guidance literature:

With oxygen; 5,15,10,20-tetraphenylporphyrin; In dichloromethane; Irradiation;

DOI:10.1016/j.tet.2005.07.081

Reference yield:

methyl-malonic acid dimethylester (609-02-9) + 5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (714964-21-3) → 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (866129-89-7)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In benzene; at 25 ℃; Irradiation;

DOI:10.1016/j.tetlet.2004.03.086

Reference yield:

4-tert-butyl-5-[3-(1-cyanoethenyl)phenyl]-3,3-dimethyl-2,3-dihydrofuran (714964-20-2) → 5-tert-butyl-1-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane (866129-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butoxide; 18-crown-6 / toluene; tetrahydrofuran / 20 °C

1.2: 52.8 percent / toluene; tetrahydrofuran / 0.13 h / 20 °C

2.1: 82.8 percent / oxygen; tetraphenylporphine / CH₂Cl₂ / Irradiation

With 18-crown-6 ether; potassium tert-butylate; oxygen; 5,15,10,20-tetraphenylporphyrin; In tetrahydrofuran; dichloromethane; toluene; 1.2: Michael addition;

DOI:10.1016/j.tet.2005.07.081

upstream raw materials:

methyl-malonic acid dimethylester

5-tert-butyl-1-[3-(1-cyanoethenyl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane

4-tert-butyl-5-{3-[1-cyano-3,3-bis(methoxycarbonyl)butyl]phenyl}-3,3-dimethyl-2,3-dihydrofuran

5-(3-bromophenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran

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