dimethyl (2Z)-2-[4-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-2,3,3a,5,6,7-hexahydro-1H-pyrrolo[1,2-a]indol-8-ylidene]butanedioate

Base Information

• Chemical Name: dimethyl (2Z)-2-[4-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-2,3,3a,5,6,7-hexahydro-1H-pyrrolo[1,2-a]indol-8-ylidene]butanedioate
• CAS No.: 81239-27-2
• Molecular Formula: C₂₂H₂₉NO₈
• Molecular Weight: 435.474
• NSC Number: 338929
• DSSTox Substance ID: DTXSID70423040
• Mol file: 81239-27-2.mol

Synonyms:NSC338929;81239-27-2;DTXSID70423040;NSC-338929

Chemical Property of dimethyl (2Z)-2-[4-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-2,3,3a,5,6,7-hexahydro-1H-pyrrolo[1,2-a]indol-8-ylidene]butanedioate

Chemical Property:

• Vapor Pressure: 7.01E-12mmHg at 25°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 435.18931688
• Heavy Atom Count: 31
• Complexity: 858

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC(=C1CCCC2=C1N3CCCC3C2(CC(=O)OC)C(=O)OC)C(=O)OC
• Isomeric SMILES: COC(=O)C/C(=C/1\CCCC2=C1N3CCCC3C2(CC(=O)OC)C(=O)OC)/C(=O)OC

Technology Process of dimethyl (2Z)-2-[4-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-2,3,3a,5,6,7-hexahydro-1H-pyrrolo[1,2-a]indol-8-ylidene]butanedioate

There total 2 articles about dimethyl (2Z)-2-[4-methoxycarbonyl-4-(2-methoxy-2-oxoethyl)-2,3,3a,5,6,7-hexahydro-1H-pyrrolo[1,2-a]indol-8-ylidene]butanedioate 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: 46.0%

1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1) + dimethyl acetylenedicarboxylate (762-42-5) → 2-[9-Methoxycarbonyl-9-methoxycarbonylmethyl-2,3,7,8,9,9a-hexahydro-1H,6H-pyrrolo[1,2-a]indol-(5E)-ylidene]-succinic acid dimethyl ester (81239-27-2)

Guidance literature:

In methanol; mole ratio of DMAD:enamine 2:1;

Reference yield: 33.0%

1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1) + dimethyl acetylenedicarboxylate (762-42-5) → 2,3,5,6,7,8,9,9a-octahydro-9-(methoxycarbonyl)-1H-pyrrolo<1,2-a>indole-9-actic acid methyl ester (70779-58-7) + <2,3,5,6,7,8,9,9a-octahydro-9-(methoxycarbonyl)-9-(methoxycarbonylmethyl)-1H-pyrrolo<1,2a>indol-5-ylidene>-butanedioic acid dimethyl ester (81239-27-2)

Guidance literature:

In methanol; 1.) -50 deg C (adding), 2.) RT, several h;

DOI:10.1016/S0040-4020(01)98870-2

upstream raw materials:

1-(1-Cyclohexen-1-yl)pyrrolidine

dimethyl acetylenedicarboxylate