Discretinine

Base Information

• Chemical Name: Discretinine
• CAS No.: 6018-40-2
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• UNII: 28R31624GX
• Nikkaji Number: J34.131B
• Wikidata: Q27254340
• Pharos Ligand ID: 23P2M8RQV6SX
• Metabolomics Workbench ID: 128233
• ChEMBL ID: CHEMBL2334885
• Mol file: 6018-40-2.mol

Synonyms:(-)-corypalmine;corypalmine

Chemical Property of Discretinine

Chemical Property:

• Vapor Pressure: 1.14E-10mmHg at 25°C
• Boiling Point: 501.2oC at 760 mmHg
• Flash Point: 256.9oC
• PSA: 51.16000
• Density: 1.29g/cm3
• LogP: 3.01140
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 461

Purity/Quality:

98%Min ^*data from raw suppliers

(+)-Corypalmine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)O)OC)C=C1)OC
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)O)OC)C=C1)OC

Technology Process of Discretinine

There total 31 articles about Discretinine 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: 86.0%

14-(S)-3,9-dibenzyloxy-2,10-dimethoxytetrahydroprotoberberine (107538-88-5) → corypalmine (6018-39-9,6018-40-2,13063-54-2,27313-86-6)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 2h; Reflux;

DOI:10.1016/j.bmc.2012.12.016

Reference yield: 85.0%

(S)-3,9,10-trimethoxyl-2-benzyloxytetrahydroprotoberberine → corypalmine (6018-39-9,6018-40-2,13063-54-2,27313-86-6)

Guidance literature:

With hydrogenchloride; In ethanol; for 2h; Reflux;

DOI:10.1016/j.bmcl.2017.01.090

Reference yield: 76.0%

o-Benzyloxy-(+/-)-corypalmine (27313-88-8) → 2,9,10-trimethoxy-berbin-3-ol (6018-39-9,6018-40-2,13063-54-2,27313-86-6)

Guidance literature:

With hydrogenchloride; In ethanol; for 2h; Heating;

upstream raw materials:

diazomethane

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

3-benzyloxy-4-methoxy-β-nitrostyrene

(S)-(6-((6-(benzyloxy)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2,3-dimethoxyphenyl)methanol

Downstream raw materials:

tetrahydropalmatine

3,4-dimethoxy-phthalic acid

4-ethoxy-5-methoxy-phthalic acid

Refernces

• 1、 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.
• 2、 Mali, R. S.,Yeola, Suresh N.. "Phenolic Berbine Alkaloids: An Improved Total Synthesis of (+/-)-Corypalmine". . p. 79 - 80. Retrieved 2007/10/02.