Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxole)-6',8'-diol, 6',7,8,8'-tetrahydro-6-methyl-, (6'R,7'S,8'S)-

Base Information

• Chemical Name: Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxole)-6',8'-diol, 6',7,8,8'-tetrahydro-6-methyl-, (6'R,7'S,8'S)-
• CAS No.: 68736-95-8
• Molecular Formula: C20H19NO6
• Molecular Weight: 369.368
• DSSTox Substance ID: DTXSID30988428
• Mol file: 68736-95-8.mol

Synonyms:68736-95-8;DTXSID30988428;Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxole)-6',8'-diol, 6',7,8,8'-tetrahydro-6-methyl-, (6'R,7'S,8'S)-;6-Methyl-6',7,8,8'-tetrahydro-2H,2'H,6H-spiro[1,3-dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-diol

Chemical Property of Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxole)-6',8'-diol, 6',7,8,8'-tetrahydro-6-methyl-, (6'R,7'S,8'S)-

Chemical Property:

• Boiling Point: 530.8°Cat760mmHg
• Flash Point: 274.8°C
• Density: 1.6g/cm³
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 369.12123733
• Heavy Atom Count: 27
• Complexity: 605

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C14C(C5=C(C4O)C6=C(C=C5)OCO6)O)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C=C2C14[C@@H](C5=C([C@@H]4O)C6=C(C=C5)OCO6)O)OCO3

Technology Process of Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxole)-6',8'-diol, 6',7,8,8'-tetrahydro-6-methyl-, (6'R,7'S,8'S)-

There total 40 articles about Spiro(1,3-dioxolo(4,5-g)isoquinoline-5(6H),7'-(7H)indeno(4,5-d)(1,3)dioxole)-6',8'-diol, 6',7,8,8'-tetrahydro-6-methyl-, (6'R,7'S,8'S)- 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: 91.0%

(+/-)-sibiricine (24181-66-6,31456-80-1,64397-09-7,64397-10-0) → (+/-)-sewercinine (24181-64-4,33805-02-6,68736-95-8,76231-96-4,99265-30-2,126187-21-1)

Guidance literature:

With sodium tetrahydroborate; In methanol;

Reference yield: 73.0%

7,8,6',8'-tetrahydro-6H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6't,8'c-diol (84229-91-4) + methyl iodide (74-88-4) → (+/-)-Ochrobirin (24181-64-4,33805-02-6,68736-95-8,76231-96-4,99265-30-2,126187-21-1)

Guidance literature:

In tetrahydrofuran; Ambient temperature;

Reference yield:

6-acetyl-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione (38854-62-5) → (+/-)-Ochrobirin (24181-64-4,33805-02-6,68736-95-8,76231-96-4,99265-30-2,126187-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Adams catalyst / acetic acid / 1810.02 Torr

2: aq. HCl / ethanol / Heating

3: HCO₂H

4: NaBH₄ / ethanol / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; formic acid; hydrogen; platinum(IV) oxide; In ethanol; acetic acid;

DOI:10.1139/v72-481

upstream raw materials:

6-methyl-7,8-dihydro-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

7,8-dihydro-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

6-acetyl-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione

6-acetyl-7,8-dihydro-6H-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6',8'-dione