34272-51-0

Basic information

• Product Name: histrionicotoxin
• Synonyms: histrionicotoxin;(2S,6R)-2α-[(Z)-2-Pentene-4-ynyl]-7α-[(Z)-1-butene-3-ynyl]-1-azaspiro[5.5]undecane-8β-ol;(2S,6R)-7α-[(Z)-1-Buten-3-ynyl]-2-[(Z)-2-penten-4-ynyl]-1-azaspiro[5.5]undecan-8β-ol
• CAS NO: 34272-51-0
• Molecular Formula: C19H25NO
• Molecular Weight: 283.4079
• Mol File: 34272-51-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 75-76°
• Boiling Point: 411.1°Cat760mmHg
• Flash Point: 84.1°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 1.78E-08mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: histrionicotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: histrionicotoxin(34272-51-0)
• EPA Substance Registry System: histrionicotoxin(34272-51-0)

Safety Data

• Hazardous Substances Data: 34272-51-0(Hazardous Substances Data)

Usage

Uses

Biochemical probe for neuromuscular transmission.

InChI:InChI=1/C19H25NO/c1-3-5-7-10-16-11-8-14-19(20-16)15-9-13-18(21)17(19)12-6-4-2/h1-2,5-7,12,16-18,20-21H,8-11,13-15H2/b7-5-,12-6-/t16-,17-,18+,19-/m1/s1

Upstream product

• 104270-45-3 [(2R,6S,7R,8R)-8-Acetoxy-7-((Z)-4-trimethylsilanyl-but-1-en-3-ynyl)-1-aza-spiro[5.5]undec-2-yl]-acetic acid ethyl ester 
• 104270-43-1 2-[(6R,7S,8S)-8-Acetoxy-7-((Z)-3-acetoxy-propenyl)-1-aza-spiro[5.5]undec-(2Z)-ylidene]-3-oxo-butyric acid ethyl ester 
• 104270-44-2 [(6S,7R,8R)-8-Acetoxy-7-((Z)-4-trimethylsilanyl-but-1-en-3-ynyl)-1-aza-spiro[5.5]undec-(2Z)-ylidene]-acetic acid ethyl ester 
• 104270-46-4 Acetic acid (2R,6S,7R,8R)-2-(2-hydroxy-ethyl)-7-((Z)-4-trimethylsilanyl-but-1-en-3-ynyl)-1-aza-spiro[5.5]undec-8-yl ester 
• 104270-42-0 Acetic acid (6R,7R,8R)-7-((Z)-3-acetoxy-propenyl)-2-oxo-1-aza-spiro[5.5]undec-8-yl ester 
• 56459-26-8 Acetic acid (6R,7R,8R)-7-but-3-enyl-2-oxo-1-aza-spiro[5.5]undec-8-yl ester 
• 104270-41-9 C₁₃H₁₉NO₂ 
• 99106-90-8 Acetic acid (6S,7R,8R)-7-((E)-but-1-en-3-ynyl)-2-((Z)-pent-2-en-4-ynyl)-1-aza-spiro[5.5]undec-8-yl ester 
• 1321494-67-0 (2S,6R,7S,8S)-2-((Z)-3-iodoallyl)-7-((Z)-2-iodovinyl)-1-azaspiro[5.5]undecan-8-ol 
• 127762-06-5 (1S,5R,8S)-1-[(Z)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-hept-6-enyl]-8-((Z)-2-iodo-vinyl)-6-oxa-bicyclo[3.2.1]octan-7-one 
• 127791-69-9 (1S,5R,8S)-1-[(S)-4-(tert-Butyl-dimethyl-silanyloxy)-hept-6-enyl]-8-vinyl-6-oxa-bicyclo[3.2.1]octan-7-one 
• 127762-07-6 Acetic acid (2S,6R,7S,8S)-2-((Z)-3-iodo-allyl)-7-((Z)-2-iodo-vinyl)-1-aza-spiro[5.5]undec-8-yl ester 

Downstream Products

• 40709-29-3 (-)-Perhydrohistrionicotoxin 

Relevant articles and documents

Total Synthesis of (?)-Histrionicotoxin through a Stereoselective Radical Translocation–Cyclization Reaction

Stereoselective total syntheses of (?)-histrionicotoxin and (?)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation–cyclization reaction involving a chiral cyclic acetal; the use of tris(trimethylsilyl)silane was crucial for the high diastereoselectivity. The cyclization product was converted into (?)-histrionicotoxin 235A through a one-pot partial-reduction–allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (?)-histrionicotoxin.

Total synthesis of (-)-histrionicotoxin

A total synthesis of (-)-histrionicotoxin was achieved. Our synthesis features preparation of a pseudosymmetrical dienyne through chirality transfer from an allenylsilane, a dienyne metathesis to produce the bicyclo [5.4.0] system in optically active form, selective functionalization of a diene via a 5-exo-trig iodoetherification, and an asymmetric propargylation.

Total syntheses of (-)-histrionicotoxin and (-)-histrionicotoxin 235A

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