552-29-4

Basic information

• Product Name: oxyhydrastinine
• Synonyms: oxyhydrastinine;7,8-Dimethyl-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5(6H)-one;Oxohydrastinine
• CAS NO: 552-29-4
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 552-29-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 96-98 °C(Solv: cyclohexane (110-82-7))
• Boiling Point: 411°Cat760mmHg
• Flash Point: 202.4°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 5.78E-07mmHg at 25°C
• Refractive Index: 1.599
• PKA: -1.19±0.20(Predicted)
• CAS DataBase Reference: oxyhydrastinine(CAS DataBase Reference)
• NIST Chemistry Reference: oxyhydrastinine(552-29-4)
• EPA Substance Registry System: oxyhydrastinine(552-29-4)

Safety Data

• Hazardous Substances Data: 552-29-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4399, 1955 DOI: 10.1021/ja01621a062

InChI:InChI=1/C11H11NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5H,2-3,6H2,1H3

Upstream product

• 66946-63-2 hydrastinine pseudo-cyanide 
• 24880-42-0 6-methyl[1,3]dioxolo[4,5-g]isoquinolin-5(6H)-one 
• 28281-84-7 2-carboxy-4,5-methylenedioxyphenylacetic acid 
• 130-86-9 protopine 
• 86138-63-8 6,7-dihydro-indeno[5,6-d][1,3]dioxol-5-one oxime 
• 140848-62-0 Acetic acid 2-[(benzo[1,3]dioxole-5-carbonyl)-methyl-amino]-1-phenylsulfanyl-ethyl ester 
• 140848-64-2 Benzo[1,3]dioxole-5-carboxylic acid (2-benzenesulfinyl-ethyl)-methyl-amide 
• 94-53-1 Piperonylic acid 
• 33542-98-2 β-<3,4-(methylenedioxy)phenyl>ethyl formamide 
• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 124-40-3 dimethyl amine 
• 140848-59-5 6-Methyl-8-phenylsulfanyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-5-one 
• 35287-11-7 6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 
• 21796-14-5 noroxyhydrastinine 

Downstream Products

• 6592-85-4 hydrastinine 
• 1132791-36-6 C₁₈H₁₄F₃NO₄ 
• 1132791-34-4 C₂₀H₁₉NO₅ 
• 1132791-35-5 C₁₈H₁₇NO₄ 
• 1132791-37-7 C₁₇H₁₄BrNO₃ 
• 1132791-33-3 C₁₉H₁₇NO₄ 
• 1132791-32-2 C₁₇H₁₅NO₃ 

Relevant articles and documents

Facile synthesis of the isoquinoline alkaloids doryanine and oxyhydrastinine

Starting from 4,5-(methylenedioxy)homophthalic acid, a concise and efficient synthesis of the isoquinoline alkaloids doryanine and oxyhydrastinine is described via the corresponding homophthalimide utilizing a one-pot regioselective reductive dehydration

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

Oxidation of N-methyltetrahydroisoquinolines with iodosylbenzene in the presence of a catalytic amount of tetrabutylammonium iodide in various solvents afforded N-methyl-2H-3,4-dihydroisoquinol-1-ones in almost quantitative yields. The application of this finding to the oxidation of other isoquinolines, including tetrahydroisoquinolines, lycorine diacetate, and benzyltetrahydroisoquinolines, also afforded the corresponding lactams in good yields, however, accompanied by a few minor byproducts. Under similar conditions, tetrahydroberberine gave a rearranged compound, berberal, as the major product, accompanied by 8-oxoberberine and berberine.

Mercuric dehydrogenations of N-tertiary piperidine derivatives with different substitution pattern

A comparison of the dehydrogenation of different N-tertiary piperidine derivatives with mercuric EDTA and mercuric acetate shows an increase of the reaction with the complex method.This is especially evident with the N-demethylation of 1,2,2,6,6-pentamethylpiperidine.Generally with dehydrogenations offering a possibility of generating a tertiary or a secondary carbenium ion, the latter alternative is mostly also realized to a minor extent.