2H-Indol-2-one, 1,3,3a,4,5,7a-hexahydro-, cis-

Base Information

• Chemical Name: 2H-Indol-2-one, 1,3,3a,4,5,7a-hexahydro-, cis-
• CAS No.: 113466-87-8
• Molecular Formula: C8H11NO
• Molecular Weight: 137.181
• Mol file: 113466-87-8.mol

Synonyms:

Chemical Property of 2H-Indol-2-one, 1,3,3a,4,5,7a-hexahydro-, cis-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Indol-2-one, 1,3,3a,4,5,7a-hexahydro-, cis-

There total 7 articles about 2H-Indol-2-one, 1,3,3a,4,5,7a-hexahydro-, cis- 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: 76.0%

2-(cyclohex-2-en-1-yl)-N-phenoxyacetamide → 2-(2-cyclohexenyl)acetamide (100556-65-8) + (3aS,7aR)-1,3,3a,4,5,7a-Hexahydro-indol-2-one (113466-87-8)

Guidance literature:

With tributyl-amine; bis(trimethylsilylmethyl)(cycloocta-1,5-diene)palladium(II); triethyl phosphite; In acetonitrile; at 80 ℃; for 24h; Reagent/catalyst; Solvent; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.6b08932

Reference yield:

cyclohexene (110-83-8) → 2-(2-cyclohexenyl)acetamide (100556-65-8) + (3aS,7aR)-1,3,3a,4,5,7a-Hexahydro-indol-2-one (113466-87-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / cyclohexane / 3 h / 88 °C

2.1: sodium hydride / mineral oil; tetrahydrofuran / 1.25 h / 0 - 20 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate; water / methanol / 2 h / 100 °C

4.1: dimethyl sulfoxide / 4 h / 120 °C

5.1: chloroformic acid ethyl ester; 4-methyl-morpholine / diethyl ether / 1 h / 0 °C / Inert atmosphere

5.2: 16 h / 20 °C / Inert atmosphere

6.1: tributyl-amine; triethyl phosphite; bis(trimethylsilylmethyl)(cycloocta-1,5-diene)palladium(II) / acetonitrile / 24 h / 80 °C / Glovebox; Sealed tube; Inert atmosphere

With 4-methyl-morpholine; N-Bromosuccinimide; lithium hydroxide monohydrate; tributyl-amine; 2,2'-azobis(isobutyronitrile); bis(trimethylsilylmethyl)(cycloocta-1,5-diene)palladium(II); water; chloroformic acid ethyl ester; sodium hydride; dimethyl sulfoxide; triethyl phosphite; In tetrahydrofuran; methanol; diethyl ether; cyclohexane; acetonitrile; mineral oil;

DOI:10.1021/jacs.6b08932

Reference yield:

rac-3-bromocyclohexene (1521-51-3,113667-32-6) → 2-(2-cyclohexenyl)acetamide (100556-65-8) + (3aS,7aR)-1,3,3a,4,5,7a-Hexahydro-indol-2-one (113466-87-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 1.25 h / 0 - 20 °C / Inert atmosphere

1.2: 18 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate; water / methanol / 2 h / 100 °C

3.1: dimethyl sulfoxide / 4 h / 120 °C

4.1: chloroformic acid ethyl ester; 4-methyl-morpholine / diethyl ether / 1 h / 0 °C / Inert atmosphere

4.2: 16 h / 20 °C / Inert atmosphere

5.1: tributyl-amine; triethyl phosphite; bis(trimethylsilylmethyl)(cycloocta-1,5-diene)palladium(II) / acetonitrile / 24 h / 80 °C / Glovebox; Sealed tube; Inert atmosphere

With 4-methyl-morpholine; lithium hydroxide monohydrate; tributyl-amine; bis(trimethylsilylmethyl)(cycloocta-1,5-diene)palladium(II); water; chloroformic acid ethyl ester; sodium hydride; dimethyl sulfoxide; triethyl phosphite; In tetrahydrofuran; methanol; diethyl ether; acetonitrile; mineral oil;

DOI:10.1021/jacs.6b08932

upstream raw materials:

cyclohexene

rac-3-bromocyclohexene

diethyl 2-(cyclohex-2-enyl)malonate

cyclohex-2-enyl-malonic acid