Sophocarpine

Base Information

• Chemical Name: Sophocarpine
• CAS No.: 6483-15-4
• Molecular Formula: C15H22N2O
• Molecular Weight: 246.352
• European Community (EC) Number: 683-124-3
• DSSTox Substance ID: DTXSID90215126
• Nikkaji Number: J359.360F
• Wikidata: Q72508561
• Metabolomics Workbench ID: 133188
• ChEMBL ID: CHEMBL377725
• Mol file: 6483-15-4.mol

Synonyms:13,14-didehydro-matridin-15-one;13,14-didehydromatridin-15-one hydrobromide;matridin-15-one, 13,14-didehydro-, monohydrobromide;sophocarpine;sophocarpine hydrobromide

Chemical Property of Sophocarpine

Chemical Property:

• Vapor Pressure: 1.92E-07mmHg at 25°C
• Melting Point: 54～55℃
• Boiling Point: 425.4 °C at 760 mmHg
• PKA: 9.59±0.20(Predicted)
• Flash Point: 194 °C
• PSA: 23.55000
• Density: 1.19 g/cm³
• LogP: 1.52350
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 246.173213330
• Heavy Atom Count: 18
• Complexity: 392

Purity/Quality:

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

Sophocarpine >99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CN3C(CC=CC3=O)C4C2N(C1)CCC4
• Isomeric SMILES: C1C[C@H]2CN3[C@H](CC=CC3=O)[C@@H]4[C@H]2N(C1)CCC4
• Uses: Sophocarpine is an intermediate in the synthesis of (+)-Matrine-d3 (M197872). (+)-Matrine-d3, is a labeled analogue of (+)-Matrine, an alkaloid compound extracted from the roots of Sophora species which maintain anti-inflammatory, anti-cancer and a host of other positive pharmacological effects. Apoptotic agent.

Technology Process of Sophocarpine

There total 5 articles about Sophocarpine 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:

14-phenylsulfinyl matrine → sophocarpine (6483-15-4)

Guidance literature:

With potassium carbonate; In toluene; for 1.5h; Reflux; Green chemistry; Large scale;

DOI:10.1016/j.tetlet.2013.12.060

Reference yield:

(+)-matrine (519-02-8) → sophocarpine (6483-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - 25 °C / Inert atmosphere; Green chemistry

1.2: Inert atmosphere; Green chemistry

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; hydrogenchloride / water / 3 h / 50 - 70 °C / Green chemistry

3.1: potassium carbonate / toluene / 1.5 h / Reflux; Green chemistry; Large scale

With hydrogenchloride; n-butyllithium; potassium carbonate; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; water; toluene;

DOI:10.1016/j.tetlet.2013.12.060

Reference yield:

14-phenylthio matrine → sophocarpine (6483-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; hydrogenchloride / water / 3 h / 50 - 70 °C

2: potassium carbonate / toluene / 1.5 h / Reflux

With hydrogenchloride; potassium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In water; toluene;

DOI:10.1016/j.bmc.2020.115305

upstream raw materials:

(+)-matrine

Downstream raw materials:

(+)-sophocarpine N-oxide

13-benzyloxy matrine

14-hydroxy-13-(4-fluoro-3-nitro)benzoyloxymatrine hydrochloride

14-hydroxy-13-benzoyloxymatrine hydrochloride

Refernces

• 1、 Li, Chaojie,Liu, Yuxiu,Wang, Qingmin. "Controllable and efficient oxidation of thioether by 2-iodoxybenzoic acid (IBX) in water: Semisynthesis of sophocarpine". . p. 950 - 953. Retrieved 2014.
• 2、 -. "A method for synthesizing sophocarpine". Paragraph 0011; 0013. . Retrieved 2017/04/08.