2-depentylperhydrohistrionicotoxin

Base Information

• Chemical Name: 2-depentylperhydrohistrionicotoxin
• CAS No.: 55228-77-8
• Molecular Formula: C₁₄H₂₇NO
• Molecular Weight: 225.374
• Hs Code.: 2933990090
• Mol file: 55228-77-8.mol

Synonyms:1-Azaspiro[5.5]undecan-8-ol,7-butyl-, (6a,7b,8a)-(?à)-; (?à)-Depentylperhydrohistrionicotoxin;1-Azaspiro[5.5]undecan-8-ol, 7-butyl-, (6a,7b,8a)-

Chemical Property of 2-depentylperhydrohistrionicotoxin

Chemical Property:

• Vapor Pressure: 3.82E-06mmHg at 25°C
• Boiling Point: 345.6°C at 760 mmHg
• Flash Point: 89.5°C
• PSA: 32.26000
• Density: 0.98g/cm³
• LogP: 3.17870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-depentylperhydrohistrionicotoxin

There total 77 articles about 2-depentylperhydrohistrionicotoxin 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: 90.0%

(6RS,7SR,8SR)-7-n-Butyl-N-benzyl-1-azaspiro<5.5>undecan-8-ol (83562-31-6) → (+/-)-depentylperhydrohistrionicotoxin (55228-77-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; Ambient temperature;

DOI:10.1016/S0040-4020(01)88171-0

Reference yield: 85.0%

7-n-Butyl-N-benzyl-1-azaspiro<5.5>undecan-8-ol (86851-83-4) → (+/-)-depentylperhydrohistrionicotoxin (55228-77-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 48h; under 3102.9 Torr;

DOI:10.1021/jo00145a057

Reference yield: 85.0%

(6R,7S,8S)-7-Butyl-1-(toluene-4-sulfonyl)-1-aza-spiro[5.5]undecan-8-ol → (+/-)-depentylperhydrohistrionicotoxin (55228-77-8)

Guidance literature:

With naphthalene; sodium; In 1,2-dimethoxyethane; for 2h;

DOI:10.1016/S0040-4020(98)01115-6

upstream raw materials:

(6S*,7S*,8S*,11S*)-7-butyl-8-((tert-butyldimethylsilyl)oxy)-11-iodo-1-(phenylmethyl)-1-azaspiro<5.5>undecane

(6SR,7SR,8SR)-7-n-butyl-8-hydroxy-1-azaspiro<5.5>undecane-2-one

7-n-Butyl-N-benzyl-1-azaspiro<5.5>undecan-8-ol

(6RS,7SR,8SR)-7-n-Butyl-N-benzyl-1-azaspiro<5.5>undecan-8-ol

Downstream raw materials:

(6RS,7SR,8RS)-7-n-butyl-1-azaspiro<5.5>undecan-8-ol

Refernces

Asymmetricsynthesis. XXXII. Formalsynthesisof (-) - Perhydrohistrionicotoxin

10.1016/S0040-4039(00)74361-9

The study details the enantioselective synthesis of (-)-depentylperhydrohistrionicotoxin 2 from the chiral synthon (-)-3. The key steps involve the formation of a spiro skeleton through an aldol cyclization of a methyl ketone and an aldehyde function. The synthesis strategy includes the condensation of (-)-3 with 2-(2-bromoethyl)-1,3-dioxolane to form 4, which upon treatment with MeLi yields imine 5. The tricyclic ketal 6 is isolated instead of the expected ketone, and its ether system is reduced with LAH/AlCl3 to form an epimeric mixture of alcohols 7. Further steps include hydrogenation, protection with benzyl bromide, Swem oxidation to ketone 9, and a series of transformations involving 1,4-reduction, butyl chain addition, dehydration, and hydroboration-oxidation to finally yield (-)-depentylperhydrohistrionicotoxin 2. The study highlights the challenges and innovative solutions in synthesizing complex natural products with high stereochemical control.