Formamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl-

Base Information

• Chemical Name: Formamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl-
• CAS No.: 60394-88-9
• Molecular Formula: C21H19NO6
• Molecular Weight: 381.385
• DSSTox Substance ID: DTXSID30209145
• Nikkaji Number: J17.916G
• Wikidata: Q83083320
• Mol file: 60394-88-9.mol

Synonyms:Arnottianamide;60394-88-9;Formamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl-;N-[6-(2-Hydroxy-3,4-dimethoxy phenyl)naphtho[2,3-d][1,3]dioxol-5-yl]-N-methylformamide;N-[6-(2-hydroxy-3,4-dimethoxyphenyl)benzo[f][1,3]benzodioxol-5-yl]-N-methylformamide;DTXSID30209145;N-[6-(2-Hydroxy-3,4-dimethoxy-phenyl)-naphtho[2,3-d][1,3]dioxol-5-yl]-N-methyl-formamide;N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho[2,3-d][1,3]dioxol-5-yl)-N-methylformamide

Chemical Property of Formamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl-

Chemical Property:

• Vapor Pressure: 9.04E-14mmHg at 25°C
• Melting Point: 264-267 °C
• Boiling Point: 573.8°Cat760mmHg
• PKA: 8.50±0.40(Predicted)
• Flash Point: 300.9°C
• PSA: 77.46000
• Density: 1.353g/cm³
• LogP: 4.18680
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 381.12123733
• Heavy Atom Count: 28
• Complexity: 547

Purity/Quality:

98%Min ^*data from raw suppliers

N-[6-(2-Hydroxy-3,4-dimethoxyphenyl)naphtho[2,3-d][1,3]dioxol-5-yl]-N-methylformamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C=O)C1=C(C=CC2=CC3=C(C=C21)OCO3)C4=C(C(=C(C=C4)OC)OC)O
• Description: Arnottianamide occurs in Xanthoxylum arnottianum and, in trace amounts, in X. cuspidatum. It crystallizes as colourless prisms from EtOH and gives an ultraviolet spectrum in ethanol with absorption maxima at 236 and 332 nm and shoulders at 280 and 324 nm. The structure has been elucidated from chemical and spectro-scopic data and confirmed by its preparation from chelerythrine chloride by a Baeyer-Villiger type oxidation of the irnmonium group. Treatment with LiA1H4 gives the deoxo derivative as colourless prisms, m.p. 200-2°C, forming a crystalline methyl derivative, m.p. l66.5-168.5°C.

Technology Process of Formamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl-

There total 3 articles about Formamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl- 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: 70.6%

chelerythrine hydrosulfate → arnottianamide (60394-88-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 40 ℃; for 5h;

Reference yield: 67.2%

chelerythrine chloride (3895-92-9) → arnottianamide (60394-88-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 40 ℃; for 3h;

DOI:10.1016/0031-9422(89)80125-6

Reference yield:

→ arnottianamide (60394-88-9)

Guidance literature:

DOI:10.1016/S0040-4039(00)78018-X

upstream raw materials:

chelerythrine chloride

Downstream raw materials:

deoxo-O-methylarnottianamide

deoxoarnottianamide

O-methylarnottianamide

Refernces

• 1、 Ishii, Hisashi,Ishikawa, Tsutomu,Lu, Sheng-Teh,Chen, Ih-Sheng. "Baeyer-Villiger-type Oxidation of an Immonium Group: The Structural Establishment of Naturally Occurring Amides Related to Benzophenanthridine Alkaloids". . p. 1769 - 1774. Retrieved 2007/10/02.