6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine

Base Information

• Chemical Name: 6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine
• CAS No.: 133111-56-5
• Molecular Formula: C21H20 Cl N
• Molecular Weight: 321.85
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20433194
• Nikkaji Number: J2.618.934I
• Wikidata: Q82247321
• ChEMBL ID: CHEMBL1689593
• Mol file: 133111-56-5.mol

Synonyms:133111-56-5;6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine;6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-1,3-dihydropyrrolizine;6-(4-Chlorophenyl)-2,3-Dihydro-2,2-Dimethyl-7-Phenyl-1H-Pyrrolizine;1H-Pyrrolizine, 6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-;SCHEMBL1839904;CHEMBL1689593;DTXSID20433194;AKOS015909801;FT-0706532;1-Phenyl-2-(4-chlorophenyl)-6,6-dimethyl-6,7-dihydro-5H-pyrrolizine

Chemical Property of 6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine

Chemical Property:

• PSA: 4.93000
• LogP: 6.05780
• Storage Temp.: 2-8°C
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 321.1284273
• Heavy Atom Count: 23
• Complexity: 406

Purity/Quality:

99%, ^*data from raw suppliers

6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2=C(C(=CN2C1)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C

Technology Process of 6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine

There total 15 articles about 6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine 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: 84.0%

4-chlorobenzoylmethyl bromide (536-38-9) + 5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole (116673-95-1) → 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine (133111-56-5)

Guidance literature:

5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole; With sodium hydrogencarbonate; In methanol;

4-chlorobenzoylmethyl bromide; In methanol; for 20h;

With water; at 40 ℃; for 1h;

DOI:10.1135/cccc2009026

Reference yield: 15.0%

4-Chlorophenylboronic acid (1679-18-1) + 2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl trifluoromethanesulfonate (226900-28-3) → 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine (133111-56-5)

Guidance literature:

With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1) rt, overnight; 2) reflux, 24 h;

DOI:10.1016/S0040-4020(99)00176-3

Reference yield:

(4-chlorphenyl)magnesium bromide (873-77-8) + N,N-diethyl 2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl carbamate (226900-31-8) → 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine (133111-56-5)

Guidance literature:

With Ni(aca)2; In tetrahydrofuran; Yield given; Heating;

DOI:10.1016/S0040-4020(99)00176-3

upstream raw materials:

4-chlorobenzoylmethyl bromide

5-benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole

4-Chlorophenylboronic acid

2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-6-yl trifluoromethanesulfonate

Downstream raw materials:

ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)hexan-1-one

1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)ethanone

1-(2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl)propan-1-one

Refernces

• 1、 Liu, Wukun,Zhou, Jinpei,Liu, Yinglin,Liu, Haoran,Bensdorf, Kerstin,Guo, Cancheng,Gust, Ronald. "Licofelone-nitric oxide donors as anticancer agents". scheme or table. p. 487 - 493. Retrieved 2011/10/18.
• 2、 Radl, Stanislav,Stach, Jan,Cerny, Josef,Klecan, Ondrej. "An efficient synthesis of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3- dihydro-lh-pyrrolizine, a key intermediate in the licofelone synthesis". experimental part. p. 1011 - 1022. Retrieved 2010/02/27.