55228-77-8

Basic information

• Product Name: 2-depentylperhydrohistrionicotoxin
• Synonyms: 2-depentylperhydrohistrionicotoxin
• CAS NO: 55228-77-8
• Molecular Formula: C14H27NO
• Molecular Weight: 225.37028
• Mol File: 55228-77-8.mol

Chemical Properties

• Boiling Point: 345.6°C at 760 mmHg
• Flash Point: 89.5°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 3.82E-06mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 2-depentylperhydrohistrionicotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: 2-depentylperhydrohistrionicotoxin(55228-77-8)
• EPA Substance Registry System: 2-depentylperhydrohistrionicotoxin(55228-77-8)

Safety Data

• Hazardous Substances Data: 55228-77-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H27NO/c1-2-3-7-12-13(16)8-6-10-14(12)9-4-5-11-15-14/h12-13,15-16H,2-11H2,1H3/t12-,13+,14?/m1/s1

Upstream product

• 88204-71-1 1-benzyl-7-butyl-1-azaspiro<5.5>undec-7-en-9-one 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 82260-32-0 (E)-4-nonen-1-ylmagnesium bromide 
• 81521-86-0 6-Hydroxy-6-((E)-non-4-enyl)-piperidin-2-one 
• 67613-85-8 7-N-butyl-8-formyloxy-1-azaspiro<5.5>undecane-2-one 
• 77204-60-5 1-benzyl-1-azaspiro<5.5>undec-7-en-9-one 
• 88367-25-3 1-Acetoxy-2-butyl-3-<4-(p-tolylsulfonoxy)butyl>cyclohex-2-ene 
• 85612-38-0 2-Butyl-3-<4-(p-tolylsulfonoxy)butyl>cyclohex-2-en-1-ol 
• 83562-26-9 (6S,7R)-1-Benzyl-7-butyl-1-aza-spiro[5.5]undecan-8-one 
• 83562-26-9 1-Benzyl-7-butyl-1-aza-spiro[5.5]undecan-8-one 
• 55228-76-7 (6SR,7SR,8SR)-7-n-butyl-8-hydroxy-1-azaspiro<5.5>undecane-2-one 
• 120883-60-5 (6S*,7S*,8S*,11S*)-7-butyl-8-((tert-butyldimethylsilyl)oxy)-11-iodo-1-(phenylmethyl)-1-azaspiro<5.5>undecane 
• 86817-86-9 O-acetyl-N-benzyldepentylperhydrohistrionicotoxin 
• 88204-70-0 1-Benzyl-7-butyl-9-trimethylsilanyloxy-1-aza-spiro[5.5]undec-8-ene 

Downstream Products

• 55228-77-8 (6RS,7SR,8RS)-7-n-butyl-1-azaspiro<5.5>undecan-8-ol 

Relevant articles and documents

Combining the [2,3] sigmatropic rearrangement and ring-closing metathesis strategies for the synthesis of spirocyclic alkaloids. A short and efficient route to (±)-perhydrohistrionicotoxin

This paper describes the use of selenium-based [2,3] sigmatropic rearrangement in combination with ruthenium-catalyzed ring-closing metathesis (RCM) for the synthesis of azaspiro ring systems, as exemplified by the reactions of model substrates 5 and 6. T

A Stereoselective Organopalladium Route toward Perhydrohistrionicotoxin

An efficient stereocontrolled route to the spirocyclic alkaloid perhydrohistrionicotoxin (2) is described.The readily available 2-substituted 1,3-cyclohexadiene 4 was converted regio- and stereoselectively to the chloro acetate 5 by using organopalladium methodology.Chemoselective SN2' displacement of the chloride via a copper-catalyzed Grignard reaction furnished 6, thus establishing the correct relative configuration at two adjacent centers.Further elaboration to the δ-amino alkene 10 was followed by a completely stereoselective iodocyclization reaction which yielded azaspirocycle 11.This compound was transformed to depentylperhydrohistrionicotoxin (3) in essentially one operation, thus completing a formal total synthesis of the title alkaloid.The overall yield of 3 from 4 was 23percent for nine operations.An alternative route to advanced intermediate 8 was also developed, the key step being the coupling of enol triflate 15 with the appropriate lithium organocuprate reagent.

Flexible Synthetic Approach to Histrionicotoxin Congeners. Formal Total Synthesis of (+/-)-Perhydrohistrionicotoxin

Conversion of 1-benzyl-1-azaspiroundec-7-en-9-one (7), readily available using simple organoiron chemistry, in six steps into (+/-)-depentylperhydrohistrionicotoxin (3) is reported.This compound has been previously reported as an intermediate for syn

Synthesis of (+/-)-Depentylperhydrohistrionicotoxin

Palladium(0)-catalysed cyclisation of 3-acetoxy-1-(4-aminoalkyl)cyclohexenes provides convenient access to the 1-azaspiroundecane ring system found in the histrionicotoxins.Hydroboration of the 7-butyl derivative (4; R1 = Bun, R

Trimethylsilyl Iodide Catalyzed Spirocyclization of Amines. Synthesis of Perhydrohistrionicotoxin

A trimethylsilyl iodide catalyzed Michael reaction of an enone amine and a trimethylsilyl iodide catalyzed SN2' spirocyclization of an allylic alcohol amine are the crucial reactions in two new syntheses of perhydrohistrionicotoxin.

(+/-)-2-Depentylperhydrohistrionicotoxin: A New Probe for a Regulatory Site on the Nicotinic Acetylcholine Receptor-Channel

(+/-)-2-Depentylperhydrohistrionicotoxin (4), several of its analogues, and N- and O-substituted derivatives were prepared and tested for their effects on the neuromuscular transmission of the frog sartorius muscle.Compound 4, its N-methyl derivative 5, the O-acetyl derivative 9, an the quaternary methiodides 19 and 20 blocked the indirectly elicited twich.The oxidation of 4 and 5 to ketones 12 and 14 and their reduction to the epimeric alcohols 17 and 18 afforded materials with substantially reduced activity.N-Acetylation of 4 to 11 changed the course of the activity to a transient potentiation of muscle twich.Both 4 and 5 were not very toxic to mice after subcutaneous administration. (+/-)-7-n-Butyl-1-azaspiroundecan-8-one (12) epimerized readily at room temperature to afford the epimer 13, and preparation of the hydrochloride of its N-methylated derivative 14 was accompanied by the 2-n-butyl-3-cyclohexene-2-one (22).The strongly hydrogen-bonded alcohol 4 was analyzed as the hydrobromide by a single-crystal X-ray analysis, confirming its structure.