l-Stepholidine

Base Information

• Chemical Name: l-Stepholidine
• CAS No.: 16562-13-3
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Hs Code.: 2933990090
• UNII: 0UPX3E69W8
• Nikkaji Number: J28.567F
• Wikipedia: Stepholidine
• Wikidata: Q27088886
• Pharos Ligand ID: 1JB6VNR5QHCP
• Metabolomics Workbench ID: 138600
• ChEMBL ID: CHEMBL487387
• Mol file: 16562-13-3.mol

Synonyms:(-)-stepholidine;L-stepholidine;stepholidine

Chemical Property of l-Stepholidine

Chemical Property:

• Vapor Pressure: 1.34E-11mmHg at 25°C
• Melting Point: 120-122°C
• Refractive Index: 1.679
• Boiling Point: 524 °C at 760 mmHg
• PKA: 9.97±0.20(Predicted)
• Flash Point: 270.7 °C
• PSA: 62.16000
• Density: 1.37 g/cm³
• LogP: 2.70840
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Complexity: 447

Purity/Quality:

99%, ^*data from raw suppliers

L-Stepholidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• Isomeric SMILES: COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O
• Description: A new alkaloid of the protoberberine group, this base occurs in Stephania giabra. The structure has been assigned on the basis of chemical and spectroscopic evidence.
• Uses: Agonist; antagonist A tetrahydroprotoberberine agonist at dopamine D1 and antagonist at D2 receptors. dyskinesia which is produced by L-DOPA or medicine to treat schizophrenia. Antipsychotics. A tetrahydroprotoberberine agonist at dopamine D1 and antagonist at D2 receptors. It is used for preventing or treating neural diseases. The neural diseases comprise parkinsonism, schizophrenia and dyskinesia which is produced by L-DOPA or medicine to treat schizophrenia. Antipsychotics.

Technology Process of l-Stepholidine

There total 89 articles about l-Stepholidine 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: 94.0%

(-)-2-benzyloxy-10-hydroxy-3,9-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine → (-)-stepholidine (16562-14-4,66142-83-4,16562-13-3)

Guidance literature:

With Raney-Ni; In methanol; Reagent/catalyst;

Reference yield: 92.5%

2-benzyloxy-10-hydroxy-3,9-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine L-tartaric acid salt → (-)-stepholidine (16562-14-4,66142-83-4,16562-13-3)

Guidance literature:

With hydrogenchloride; In ethanol; water; Reagent/catalyst; Reflux;

Reference yield: 86.0%

14-(S)-3,9-dimethoxyl-2,10-diisopropoxy-tetrahydroprotoberberine (1260522-95-9) → (-)-stepholidine (16562-14-4,66142-83-4,16562-13-3)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 - 20 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.3987/COM-10-12056

upstream raw materials:

(S)-2,10-dibenzyloxy-3,9-dimethoxytetrahydroprotoberberine

2-(2-(tert-butyldimethylsilyloxy)ethyl)-5-isopropoxy-4-methoxybenzaldehyde

(4-isopropoxy-3-methoxyphenyl)-N,N-dimethylmethanamine

methyl 6-(chloromethyl)-3-isopropoxy-2-methoxybenzoate

Refernces

• 1、 -. "Preparation method for stepholidine and derivatives thereof". . . Retrieved 2016/10/07.
• 2、 Sun, Haifeng,Zhu, Liyuan,Yang, Huicui,Qian, Wangke,Guo, Lin,Zhou, Shengbin,Gao, Bo,Li, Zeng,Zhou, Yu,Jiang, Hualiang,Chen, Kaixian,Zhen, Xuechu,Liu, Hong. "Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D1, D2 and serotonin 5-HT1A multi-action profile". supporting information. p. 856 - 868. Retrieved 2013/03/13.