Withasomnine

Base Information

• Chemical Name: Withasomnine
• CAS No.: 10183-74-1
• Molecular Formula: C12H12 N2
• Molecular Weight: 184.241
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00331987
• Nikkaji Number: J15.580B
• Wikidata: Q27108562
• Metabolomics Workbench ID: 69487
• Mol file: 10183-74-1.mol

Synonyms:withasomnine

Chemical Property of Withasomnine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 116-117 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 358.818°C at 760 mmHg
• PKA: 2.47±0.20(Predicted)
• Flash Point: 170.807°C
• PSA: 17.82000
• Density: 1.183g/cm³
• LogP: 2.49630
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 184.100048391
• Heavy Atom Count: 14
• Complexity: 199

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C=NN2C1)C3=CC=CC=C3

Technology Process of Withasomnine

There total 49 articles about Withasomnine 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: 95.0%

2-methylsulfanyl-3-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (23995-20-2) → withasomnine (10183-74-1)

Guidance literature:

With Raney Ni; In ethanol; at 20 ℃;

DOI:10.1039/c4sc00107a

Reference yield: 90.0%

3-trifluoromethanesulfonyloxy-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (1326316-10-2) + phenylboronic acid (98-80-6) → withasomnine (10183-74-1)

Guidance literature:

With Aliquat 336; sodium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine; In 1,2-dimethoxyethane; water; at 130 ℃; for 1h; Microwave irradiation;

DOI:10.1016/j.tetlet.2011.06.061

Reference yield: 78.0%

6-dihydro-3-phenyl-2-(phenylsulfonyl)-4H-pyrrolo[1,2-b]pyrazole (1314297-86-3) → withasomnine (10183-74-1)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; for 24h; Inert atmosphere;

DOI:10.1021/ol201534f

upstream raw materials:

(E)-1-Butylsulfanyl-6-chloro-2-phenyl-hex-1-en-3-one

Toluene-4-sulfonic acid 3-(2-benzenesulfonyl-4-phenyl-2H-pyrazol-3-yl)-propyl ester

3a,4,5,6-tetrahydro-3-oxo-3H-pyrrolo[1,2-c][1,2,3]oxadiazol-7-ium ylide

phenylacetylene

Refernces

• 1、 Kulinkovich, Oleg,Masalov, Nikolai,Tyvorskii, Vladimir,De Kimpe, Norbert,Keppens, Marian. "New synthetic route to the alkaloid withasomnine by ring transformation of a functionalized cyclopropanol via the parent pyrrolo[1,2-b]pyrazole". . p. 1095 - 1096. Retrieved 1996.
• 2、 Harusawa, Shinya,Hayama, Noboru,Kubo, Yumika,Kuroiwa, Nao,Nakamizu, Ayaka,Nishikawa, Kohei,Ono, Jun,Takagaki, Toshiki,Tatsui, Yuya,Usami, Yoshihide,Yoneyama, Hiroki. "Cui-catalyzed coupling reactions of 4-iodopyrazoles and alcohols: Application toward withasomnine and Homologs". . . Retrieved 2021/06/21.
• 3、 Galeta, Juraj,Tenora, Luká?,Man, Stanislav,Potá?ek, Milan. "Dihydropyrrolo[1,2-b]pyrazoles: Withasomnine and related compounds". . p. 7139 - 7146. Retrieved 2013/07/26.