(E)-1-Cinnamoylpyrrolidine

Base Information

• Chemical Name: (E)-1-Cinnamoylpyrrolidine
• CAS No.: 52438-21-8
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.268
• Nikkaji Number: J1.145.175F
• Wikidata: Q76145190
• Metabolomics Workbench ID: 48343
• Mol file: 52438-21-8.mol

Synonyms:(E)-1-Cinnamoylpyrrolidine;(Z)-3-phenyl-1-pyrrolidin-1-ylprop-2-en-1-one;1-cis-Cinnamoylpyrrolidine;CHEBI:187055;(2Z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one

Chemical Property of (E)-1-Cinnamoylpyrrolidine

Chemical Property:

• Melting Point: 123℃
• PSA: 20.31000
• LogP: 2.26010
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 201.115364102
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

98%Min ^*data from raw suppliers

1-Cinnamoylpyrrolidine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCN(C1)C(=O)C=CC2=CC=CC=C2
• Isomeric SMILES: C1CCN(C1)C(=O)/C=C\C2=CC=CC=C2

Technology Process of (E)-1-Cinnamoylpyrrolidine

There total 29 articles about (E)-1-Cinnamoylpyrrolidine 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: 97.0%

pyrrolidine (123-75-1) + (E)-3-phenylacrylic acid (140-10-3) → 1-trans-cinnamoylpyrrolidine (19202-21-2,52438-21-8)

Guidance literature:

With 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2008.09.094

Reference yield: 96.0%

pyrrolidine (123-75-1) + Cinnamoyl chloride (102-92-1,17082-09-6) → 1-trans-cinnamoylpyrrolidine (19202-21-2,52438-21-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1002/hlca.200290012

Reference yield: 95.0%

(N-pyrrolidinylcarbonylmethyl)triphenylarsonium bromide (112601-96-4) + benzaldehyde (100-52-7) → 1-trans-cinnamoylpyrrolidine (19202-21-2,52438-21-8)

Guidance literature:

With potassium carbonate; In acetonitrile; at 25 ℃; for 10h;

DOI:10.1016/S0040-4039(00)96069-6

upstream raw materials:

N-trimethylsilylpyrrolidine

trans-cinnamoyl fluoride

E-styryl iodide

trimethylpyrrolidinylcarbonylstannane

Downstream raw materials:

1-{[(2S,3R)-3-phenylaziridin-2-yl]carbonyl}pyrrolidine

[(1S,2S,3R)-2-Phenyl-3-((E)-2-trimethylsilanyl-vinyl)-cyclopropyl]-pyrrolidin-1-yl-methanone

3-(4-(1H-pyrrol-1-yl)phenyl)-3-phenyl-1-(pyrrolidin-1-yl)propan-1-one

potassium 3-phenyl-1-(pyrrolidin-1-yl)-3-(trifluoroborato)propan-1-one

Refernces

• 1、 Sandoval, Braddock A.,Clayman, Phillip D.,Oblinsky, Daniel G.,Oh, Seokjoon,Nakano, Yuji,Bird, Matthew,Scholes, Gregory D.,Hyster, Todd K.. "Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)". supporting information. p. 3662 - 3662. Retrieved 2021/04/09.
• 2、 Yang, Tianlong,Lu, Maojian,Lin, Zhaowei,Huang, Mingqiang,Cai, Shunyou. "Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides". supporting information. p. 449 - 453. Retrieved 2019/01/24.