60594-55-0

Basic information

• Product Name: (+/-)-β-Hydrastine
• Synonyms: (3S)-rel-6,7-DiMethoxy-3-[(5R)-5,6,7,8-tetrahydro-6-Methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone
• CAS NO: 60594-55-0
• Molecular Formula: C₂₁H₂₁NO₆
• Molecular Weight: 383.39454
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 60594-55-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (+/-)-β-Hydrastine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-β-Hydrastine(60594-55-0)
• EPA Substance Registry System: (+/-)-β-Hydrastine(60594-55-0)

Safety Data

• Hazardous Substances Data: 60594-55-0(Hazardous Substances Data)

Upstream product

• 5936-28-7 (+)-β-hydrastine hydrochloride 
• 35287-11-7 6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 
• 73563-23-2 3-bromo-6,7-dimethoxyphthalide 
• 62059-59-0 methyl 6-formyl-2,3-dimethoxybenzoate 
• 519-05-1 opianic acid 
• 569-31-3 meconin 
• 191847-31-1 (2-benzo[1,3]dioxol-5-yl-ethyl) carbaminic acid tert-butyl ester 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 50-00-0 formaldehyd 
• 68780-75-6 C₂₀H₁₉NO₆ 
• 191847-32-2 tert-butyl (2-(6-iodobenzo[d][1,3]dioxol-5-yl)ethyl)carbamate 
• 118-08-1 hydrastine 
• 78179-06-3 5-((R)-4,5-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium 

Downstream Products

• 478-13-7 (-)-Ophiocarpin 
• 118-08-1 hydrastine 
• 569-31-3 meconin 
• 29617-43-4 (+)-Hydrastine 
• 485-49-4 (+/-)-Adlumidine 

Relevant articles and documents

Studies on asymmetric total synthesis of (?)-β-hydrastineviaa chiral epoxide ring-opening cascade cyclization strategy

Herein, facile and enantioselective approaches to synthesize the core phthalide tetrahydroisoquinoline scaffold of (?)-β-hydrastineviaboth a CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) epoxide ring-opening/transesterification cascade cyclization from chiral epoxide under very mild conditions are described. The key elements include a highly enantioselective epoxidation using the Shi ketone catalyst and an intramolecular CF3COOH-catalyzed cascade cyclization in one pot, and a late-stage C-3′ epimerization under MeOK/MeOH conditions as the key steps to achieve the first total synthesis of (?)-β-hydrastine (up to 81% ee).

Some Reactions of β-Hydrastine

β-Hydrastine (I) is an erythro compound, the chiral centres at C-1 and C-9 having R and S configurations respectively.Its conversion into the hitherto unknown threo-isomer by the reduction of the corresponding immonium derivative (II) with zinc and acetic acid has met with failure.Surprisingly, II with Zn/ AcOH regenerates β-hydrastine.During this reduction II rather suffers reductive cleavage yielding the non-nitrogenous lactone, meconine (IV).Sodium borohydride and catalytic reductions of II also fail to afford the threo-isomer.The latter is found to be extremely unstable as revealed from Dreiding model because of the severe steric interaction between the axial hydrogen at C-4 and the C1'-C2'bond.Benzylic oxidation of β-hydrastine (I) with MnO2, instead of producing the desired 4-oxo derivative (VI), gives 6,7-methylenedioxyisoquinoline arising out of cleavage at C1-C9 bond.

Alkaloids of Corydalis incisa Pers. V. The structures of corydalispirone and corydalisol

-