Perhydrohistrionicotoxin

Base Information

• Chemical Name: Perhydrohistrionicotoxin
• CAS No.: 40709-29-3
• Molecular Formula: C₁₉H₃₇NO
• Molecular Weight: 295.509
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40961106
• Nikkaji Number: J353.956C
• Wikidata: Q76009953
• Mol file: 40709-29-3.mol

Synonyms:2-epi-(+-)-perhydrohistrionicotoxin;H(12)-HTX;perhydrohistrionicotoxin;perhydrohistrionicotoxin, (6alpha(S*),7beta,8alpha)-(+-)-isomer

Chemical Property of Perhydrohistrionicotoxin

Chemical Property:

• Vapor Pressure: 1.59E-08mmHg at 25°C
• Boiling Point: 412.4°C at 760 mmHg
• Flash Point: 52.2°C
• PSA: 32.26000
• Density: 0.95g/cm³
• LogP: 5.12760
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 295.287514804
• Heavy Atom Count: 21
• Complexity: 293

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1CCCC2(N1)CCCC(C2CCCC)O
• Isomeric SMILES: CCCCC[C@@H]1CCC[C@@]2(N1)CCC[C@@H]([C@H]2CCCC)O

Technology Process of Perhydrohistrionicotoxin

There total 92 articles about Perhydrohistrionicotoxin 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: 94.0%

8-Oxoperhydrohistrionicotoxin (120851-30-1) → 8-epi-Perhydrohistrionicotoxin (120851-29-8) + (-)-Perhydrohistrionicotoxin (40709-29-3)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 24h; Yields of byproduct given;

DOI:10.1021/ja00195a042

Reference yield: 89.0%

(1R,5R,8S,12S)-(1'Z)-12-(but-1'-enyl)-5-pentyl-6-aza-7-oxatricyclo[6.3.1.0(1,6)]dodecane → (-)-Perhydrohistrionicotoxin (40709-29-3)

Guidance literature:

(1R,5R,8S,12S)-(1'Z)-12-(but-1'-enyl)-5-pentyl-6-aza-7-oxatricyclo[6.3.1.0(1,6)]dodecane; With hydrogenchloride; palladium(II) hydroxide/carbon; hydrogen; In tetrahydrofuran; water; at 20 ℃; for 14h; under 1292.9 Torr;

With sodium hydrogencarbonate; In water; ethyl acetate;

DOI:10.1002/chem.201001435

Reference yield: 85.0%

(2R,6S,7R,8R)-1-Benzyl-7-butyl-2-pentyl-1-aza-spiro[5.5]undecan-8-ol → 2-epi-(+/-)-perhydrohistrionicotoxin (40709-29-3,55254-30-3,59203-14-4,82042-26-0,82042-27-1,82042-29-3,85505-98-2,85505-99-3,85506-03-2,120851-29-8,122675-03-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 20h; under 760.051 Torr;

DOI:10.1021/ol020052o

upstream raw materials:

(6R,7S,8S)-7-butyl-8-hydroxy-2-pentyl-1-azaspiro<5.5>undec-1-ene

8-Oxoperhydrohistrionicotoxin

(-)-histrionicotoxin

isodihydrohistrionicotoxin