Phenylmethyl 3-oxo-2-(2-propen-1-yl)-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: Phenylmethyl 3-oxo-2-(2-propen-1-yl)-1-pyrrolidinecarboxylate
• CAS No.: 776316-72-4
• Molecular Formula: C₁₅H₁₇NO₃
• Molecular Weight: 259.305
• DSSTox Substance ID: DTXSID501181119
• Mol file: 776316-72-4.mol

Synonyms:DTXSID501181119;Phenylmethyl 3-oxo-2-(2-propen-1-yl)-1-pyrrolidinecarboxylate;776316-72-4

Chemical Property of Phenylmethyl 3-oxo-2-(2-propen-1-yl)-1-pyrrolidinecarboxylate

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 259.12084340
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCC1C(=O)CCN1C(=O)OCC2=CC=CC=C2

Technology Process of Phenylmethyl 3-oxo-2-(2-propen-1-yl)-1-pyrrolidinecarboxylate

There total 3 articles about Phenylmethyl 3-oxo-2-(2-propen-1-yl)-1-pyrrolidinecarboxylate 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%

5-Allyl-4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (214191-30-7) → 2-allyl-3-oxo-pyrrolidine-1-carboxylic acid benzyl ester (776316-72-4)

Guidance literature:

With water; sodium chloride; In dimethyl sulfoxide; at 120 - 130 ℃; for 3h;

DOI:10.1016/j.tetlet.2010.04.019

Reference yield:

ethyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate (149117-84-0) → 2-allyl-3-oxo-pyrrolidine-1-carboxylic acid benzyl ester (776316-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / benzene / Heating

2: 68 percent / NaCl; H₂O / dimethylsulfoxide / 6 h / 120 - 130 °C

With water; sodium hydride; sodium chloride; In dimethyl sulfoxide; benzene;

DOI:10.1055/s-2007-991054

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 2-allyl-3-oxo-pyrrolidine-1-carboxylic acid benzyl ester (776316-72-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / K₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

2: 65 percent / NaH / benzene / 3 h / Heating

3: aq. HCl / 5 h / Heating

With hydrogenchloride; sodium hydride; potassium carbonate; In dichloromethane; benzene;

DOI:10.1016/j.tetlet.2004.07.101

upstream raw materials:

5-Allyl-4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

ethyl 2-(((benzyloxy)carbonyl)amino)pent-4-enoate

benzyl chloroformate

Downstream raw materials:

indolizino[1,2-b]quinolin-9(11H)-one

5b,11-dihydro-6H-indolizino[1,2-b]quinolin-9-one

camptothecin

C₁₇H₂₁O₄N