cabenegrin A-I

Base Information

• Chemical Name: cabenegrin A-I
• CAS No.: 84297-59-6
• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.386
• UNII: ZAX2I4Y14X
• Nikkaji Number: J533.790I,J2.043.886J
• Wikidata: Q27295242
• Mol file: 84297-59-6.mol

Synonyms:cabenegrin A-I;Cabenegrin A I;(-)-Cabenegrin A-I;Cabenegrin A-I [MI];UNII-ZAX2I4Y14X;ZAX2I4Y14X;6H-(1,3)Dioxolo(5,6)benzofuro(3,2-C)(1)benzopyran-3-ol, 6a,12a-dihydro-4-((2E)-4-hydroxy-3-methyl-2-buten-1-yl)-, (6aR,12aR)-;84297-59-6;Cabenegrina A;Q27295242

Chemical Property of cabenegrin A-I

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 553.741°C at 760 mmHg
• Flash Point: 288.692°C
• Density: 1.389g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 368.12598835
• Heavy Atom Count: 27
• Complexity: 579

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC2=C1OCC3C2OC4=CC5=C(C=C34)OCO5)O)CO
• Isomeric SMILES: C/C(=C\CC1=C(C=CC2=C1OC[C@@H]3[C@H]2OC4=CC5=C(C=C34)OCO5)O)/CO

Technology Process of cabenegrin A-I

There total 13 articles about cabenegrin A-I 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: 74.0%

(E)-4-((6aS,12aS)-3-Hydroxy-6a,12a-dihydro-6H-5,8,10,12-tetraoxa-benzo[a]cyclopenta[h]fluoren-4-yl)-2-methyl-but-2-enoic acid ethyl ester (84666-39-7,91178-00-6) → rac-cabenegrin A-I (84297-59-6,84710-82-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -40 ℃; for 1h;

DOI:10.1016/S0040-4039(00)87727-8

Reference yield: 31.0%

(-)-3-hydroxy-4-[(E)-2-ethoxycarbonyl-2-buten-4-yl]-8,9-methylenedioxypterocarpan → (-)-3-hydroxy-4-[(E)-2-hydroxymethyl-2-buten-4-yl]-8,9-methylenedioxypterocarpan (84297-59-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00490-1

Reference yield:

2-(chloromercurio)-4,5-(methylenedioxy)phenol (61080-20-4) → rac-cabenegrin A-I (84297-59-6,84710-82-7)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium chloropalladite / acetone; H₂O

2: 80 percent / H₂ / 5percent Pd-C / acetone

3: K₂CO₃ / acetone

4: 55 percent / N,N-diethylaniline / Heating

6: 86 percent / sodium metaperiodate

7: 82 percent / dimethylsulfoxide / 1 h / 120 °C

8: 74 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -40 °C

With sodium periodate; lithium aluminium tetrahydride; lithium tetrachloropalladate(II); hydrogen; potassium carbonate; N,N-diethylaniline; palladium on activated charcoal; In tetrahydrofuran; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4039(00)87727-8

upstream raw materials:

(-)-3-hydroxy-4-(2-oxo)ethyl-8,9-methylenedioxypterocarpan

(E)-4-((6aS,12aS)-3-Hydroxy-6a,12a-dihydro-6H-5,8,10,12-tetraoxa-benzo[a]cyclopenta[h]fluoren-4-yl)-2-methyl-but-2-enoic acid ethyl ester

2-(chloromercurio)-4,5-(methylenedioxy)phenol

1-(benzyloxy)-3-(prop-2-yn-1-yloxy)benzene