cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

Base Information

• Chemical Name: cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole
• CAS No.: 2144-87-8
• Molecular Formula: C8H13N
• Molecular Weight: 123.198
• Hs Code.: 2933990090
• UNII: TT9ML8F6ID
• Mol file: 2144-87-8.mol

Synonyms:cis-2,3,3a,4,7,7a-hexahydro-1h-isoindole;2144-87-8;(3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-isoindole;TT9ML8F6ID;1802685-16-0;(cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole;(3aS,7aR)-2,3,3a,4,7,7a-hexahydro-1H-isoindole;3a,4,7,7a-Tetrahydroisoindoline, cis-;Isoindoline, 3a,4,7,7a-tetrahydro-, cis-;2,3,3a,4,7,7a-hexahydro-1H-isoindole, cis;1H-Isoindole, 2,3,3a,4,7,7a-hexahydro-, (3aR,7aS)-rel-;UNII-TT9ML8F6ID;SCHEMBL1425396;HWZHYUCYEYJQTE-OCAPTIKFSA-N;MFCD08848198;cis-3a,4,7,7a-tetrahydroisoindoline;AKOS006288584;MCULE-8856314712;AS-47512;CS-0340557;EN300-244076;F14019;(3aR,7aS)-rel-2,3,3a,4,7,7a-Hexahydro-1H-isoindole;rel-(3aR,7aS)-2,3,3a,4,7,7a-Hexahydro-1H-isoindole

Chemical Property of cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

Chemical Property:

• Boiling Point: 183℃
• PKA: 11.15±0.20(Predicted)
• Flash Point: 61℃
• PSA: 12.03000
• Density: 0.947
• LogP: 1.50080
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 123.104799419
• Heavy Atom Count: 9
• Complexity: 115

Purity/Quality:

99.90% ^*data from raw suppliers

Cis-2,3,3a,4,7,7a-Hexahydro-1H-isoindole 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC2C1CNC2
• Isomeric SMILES: C1C=CC[C@@H]2[C@H]1CNC2

Technology Process of cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

There total 2 articles about cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole 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: 87.0%

cis-1,2,3,6-Tetrahydrophthalimide (1469-48-3,565227-54-5) → (cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole (2144-87-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 60 ℃;

Reference yield:

→ (cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole (2144-87-8)

Guidance literature:

With lithium aluminium tetrahydride; diethyl ether;

DOI:10.1021/jo01364a014

Reference yield: 74.0%

(cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole (2144-87-8) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl 1,3,3a,4,7,7a-hexahydro-2H-isoindole-2-carboxylate

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 16h;

upstream raw materials:

cis-1,2,3,6-Tetrahydrophthalimide

Downstream raw materials:

((3ar,7ac)-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-acetonitrile

N-phenyloxycarbonyl-meso-8-azabicyclo[4.3.0]non-3-ene

(3aR,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate

N-BOC-octahydro-1H-isoindol-5-ol

Refernces

• 1、 Clark, Joseph R.,Dixon, Charlie F.,Feng, Kaibo,Han, Wei,Ide, Takafumi,Koch, Vanessa,Teng, Dawei,Wendell, Chloe I.,White, M. Christina. "Late-Stage Intermolecular Allylic C-H Amination". supporting information. p. 14969 - 14975. Retrieved 2021/10/01.
• 2、 Cioffi, Christopher L.,Racz, Boglarka,Varadi, Andras,Freeman, Emily E.,Conlon, Michael P.,Chen, Ping,Zhu, Lei,Kitchen, Douglas B.,Barnes, Keith D.,Martin, William H.,Pearson, Paul G.,Johnson, Graham,Blaner, William S.,Petrukhin, Konstantin. "Design, Synthesis, and Preclinical Efficacy of Novel Nonretinoid Antagonists of Retinol-Binding Protein 4 in the Mouse Model of Hepatic Steatosis". . p. 5470 - 5500. Retrieved 2019/06/07.