119736-64-0

Basic information

• Product Name: (6R,8S)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-8-ol
• CAS NO: 119736-64-0
• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.368
• Mol File: 119736-64-0.mol

Chemical Properties

• Boiling Point: 511.3°C at 760 mmHg
• Flash Point: 263°C
• Density: 1.478g/cm³
• Vapor Pressure: 2.81E-11mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: (6R,8S)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,8S)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-8-ol(119736-64-0)
• EPA Substance Registry System: (6R,8S)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-8-ol(119736-64-0)

Safety Data

• Hazardous Substances Data: 119736-64-0(Hazardous Substances Data)

Upstream product

• 494-55-3 N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 52315-62-5 3,4-(methylenedioxy)phthalaldehyde 
• 64397-08-6 (+/-)-adlumidine 
• 75267-17-3 5-Formyl-benzo[1,3]dioxole-4-carboxylic acid ethyl ester 
• 1077-75-4 (4-hydroxymethyl-benzo[1,3]dioxol-5-yl)methanol 
• 4741-65-5 6,7-methylenedioxy-phthalide 
• 56083-00-2 (+/-)-bicuculline 
• 131681-58-8 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 131589-15-6 -(1,3-benzodioxol-5-yl)(5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinolin-5-yl)methyl 2,2-dimethylpropanoic acid ester 
• 131589-14-5 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-(2,2-dimethyl-1-oxopropyl)-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 131079-60-2 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 
• 131589-16-7 (1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one 
• 131681-57-7 -α-1,3-benzodioxol-5-yl-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo<4,5-g>isoquinoline-5-methanol 

Relevant articles and documents

Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines

A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine (1a-c), as well as capnoidine and corytensine (2a,b), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler-Napieralsky reaction from amine 11. The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 (3).

Lewis acid complexed heteroatom carbanions; a convenient route to α-hydroxybenzyltetrahydroisoquinoline alkaloids

Treatment of the BF3 complex of 6,7-methylenedioxy-2-methyltetrahydroisoquinoline (2) with secbutyllithium followed by addition of piperonal gave α-hydroxybenzyltetrahydroisoquinolines 3a and 3b, while addition of 3,4-methylenedioxyphthaldehyde (4) afforded alkaloids (±)corytensine (5) and (±) egenine (6) along with isomeric hemiacetals 7 and 8.

Synthetic and Stereochemical Studies on Phthalideisoquinoline Hemiacetals

The two new phthalideisoquinoline hemiacetals rac-egenine (3) and rac-corytensine (4) are prepared by stereoselective DIBAL reduction of rac-bicuculline (1) and rac-adlumidine (2), respectively.The identity of egenine (3) with decumbensine as well as of corytensine (4) with epi-α-decumbensine and humosine A is postulated.The configuration around the anomeric center in natural (+)-egenine (3), (+)-corytensine (4) and (-)-narcotine hemiacetal (7) is deduced as (7'S), (7'R) and (7'R), respectively.