Decumbenine B

Base Information

• Chemical Name: Decumbenine B
• CAS No.: 164991-68-8
• Molecular Formula: C₁₈H₁₃NO₅
• Molecular Weight: 323.305
• DSSTox Substance ID: DTXSID501166636
• Nikkaji Number: J661.754I
• Wikidata: Q104667408
• ChEMBL ID: CHEMBL5188964
• Mol file: 164991-68-8.mol

Synonyms:Decumbenine B;164991-68-8;5-(1,3-Dioxolo[4,5-f]isoquinolin-8-yl)-1,3-benzodioxole-4-methanol;[5-([1,3]dioxolo[4,5-f]isoquinolin-8-yl)-1,3-benzodioxol-4-yl]methanol;CHEMBL5188964;DTXSID501166636

Chemical Property of Decumbenine B

Chemical Property:

• Melting Point: 226-227℃
• PSA: 70.04000
• Density: 1.481
• LogP: 2.85150
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 323.07937252
• Heavy Atom Count: 24
• Complexity: 463

Purity/Quality:

95%-98% ^*data from raw suppliers

DecumbenineB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1OC2=C(O1)C3=CC(=NC=C3C=C2)C4=C(C5=C(C=C4)OCO5)CO
• Uses: Decumbenine B is a novel isouinoline alkaloid similar to Decumbenine (D226905), an alkaloid extracted from the Corydalis decumbens species which displays pharmacological activity as described in Chinese medicinal preparations.

Technology Process of Decumbenine B

There total 26 articles about Decumbenine B 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: 68.4%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 8-(benzo[d][1,3]dioxol-5-yl)[1,3]dioxolo[4,5-f]isoquinoline → decumbenine B (164991-68-8)

Guidance literature:

With rhodium(III) chloride hydrate; dimethyl zinc(II); zinc dibromide; In tetrahydrofuran; toluene; for 24h; Sealed tube; Inert atmosphere;

Reference yield: 52.0%

N-(4-iodobenzo[1,3]dioxol-5-ylmethylene)-tert-butylamine + (5-ethynylbenzo[1,3]-dioxol-4-yl)methanol (241813-21-8) → decumbenine B (164991-68-8)

Guidance literature:

With sodium carbonate; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 48h;

DOI:10.1021/ol990067v

Reference yield: 41.0%

[5-(6,7,8,9-Tetrahydro-[1,3]dioxolo[4,5-f]isoquinolin-8-yl)-benzo[1,3]dioxol-4-yl]-methanol (219474-39-2) → decumbenine B (164991-68-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 24h; Heating;

upstream raw materials:

[5-(6,7,8,9-Tetrahydro-[1,3]dioxolo[4,5-f]isoquinolin-8-yl)-benzo[1,3]dioxol-4-yl]-methanol

(5-ethynylbenzo[1,3]-dioxol-4-yl)methanol

4-Methyl-benzo[1,3]dioxole-5-carboxylic acid diethylamide

5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester

Refernces

• 1、 Guo, Li,Lai, Ruizhi,Lv, Songyang,Nie, Ruifang,Wang, Qiantao,Wu, Yong,Xu, Yingying. "Water-mediated C-H activation of arenes with secure carbene precursors: The reaction and its application". supporting information. p. 11418 - 11421. Retrieved 2019/09/30.
• 2、 Wada, Yasuhiro,Nishida, Naoto,Kurono, Nobuhito,Ohkuma, Takashi,Orito, Kazuhiko. "Synthesis of a 3-arylisoquinoline alkaloid, decumbenine B". . p. 4320 - 4327. Retrieved 2008/03/18.