480-84-2

Basic information

• Product Name: hastanecine
• Synonyms: hastanecine;(1S,7aβ)-Hexahydro-7β-hydroxy-1H-pyrrolizine-1-methanol
• CAS NO: 480-84-2
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.2102
• Mol File: 480-84-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 261.9°Cat760mmHg
• Flash Point: 131.3°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 0.0016mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: hastanecine(CAS DataBase Reference)
• NIST Chemistry Reference: hastanecine(480-84-2)
• EPA Substance Registry System: hastanecine(480-84-2)

Safety Data

• Hazardous Substances Data: 480-84-2(Hazardous Substances Data)

Usage

General Description

Hastanecine is a synthetic chemical compound that has been studied for its potential anti-cancer and anti-inflammatory properties. It is a natural product derived from the fungus Penicillium verrucosum and has shown promising results in preclinical studies for its ability to inhibit the growth of cancer cells and reduce inflammation. Hastanecine has been found to disrupt the microtubule network in cells, leading to cell cycle arrest and ultimately, cell death. It also exhibits anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines. Further research is needed to fully understand the mechanisms of action and potential therapeutic applications of hastanecine.

InChI:InChI=1/C8H15NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h6-8,10-11H,1-5H2/t6-,7-,8+/m1/s1

Upstream product

• 86534-23-8 1(S)-acetoxy-6(R)-(2-formyloxyprop-2-yl)-7(S)-<(benzyloxy)methyl>-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 41646-10-0 2,3,5,6-Tetrahydro-1H-pyrrolizin-7-carbonsaeure-ethylester 
• 85365-57-7 ethyl (+/-)-1-hydroxy-2,3,5,6-tetrahydro-1H-pyrrolizine-7-carboxylate 
• 86534-28-3 1(R)-acetoxy-7(S)-(acetoxymethyl)-7a(S)-hexahydro-6-iodo-3H-pyrrolizin-3-one 
• 94202-33-2 (R)-2-Acetoxy-N-((E)-5-benzyloxy-2,2-dimethyl-pent-3-enyl)-succinamic acid 
• 86534-22-7 (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione 
• 86545-49-5 4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3(E)-en-1yl>-5-hydroxy-2-pyrrolidinone 
• 86534-24-9 (+)-1(S)-acetoxy-7(S)-<(benzyloxy)methyl>-6(R)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 86534-27-2 1(R)-acetoxy-7(S)-(acetoxymethyl)-6(S)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 86534-25-0 (+)-7(S)-<(benzyloxy)methyl>-1(R)-hydroxy-6(S)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 86534-29-4 1(R)-acetoxy-7(S)-acetoxymethyl-7a(S)-hexahydro-3H-pyrrolizin-3-one 
• 86534-26-1 1(R)-hydroxy-7(S)-(hydroxymethyl)-6(S)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 151385-15-8 (3E,5S)-5-(methoxymethoxymethyl)-7-phthalimido-1-O-(triphenylmethyl)hept-3-en-1-ol 
• 151385-17-0 (2S,3S)-1-(tert-butoxxycarbonyl)-2-<(R)-1-hydroxy-3-(triphenylmethoxy)propyl>-3-(methoxymethoxymethyl)pyrrolidine 

Relevant articles and documents

Asymmetric syntheses of (?)-hastanecine, (?)-turneforcidine and (?)-platynecine

Concise total asymmetric syntheses of three diastereoisomeric 1-hydroxymethyl-7-hydroxy substituted pyrrolizidines, (?)-hastanecine, (?)-turneforcidine and (?)-platynecine, are reported. The doubly diastereoselective conjugate additions of lithium (R)- or (S)-N-benzyl-N-(α-methylbenzyl)amide to tert-butyl (R,E)-4-(triethylsilyloxy)hepta-2,6-dienoate [which was prepared (in 96:4 e.r.) via Lewis acid mediated catalytic asymmetric allylation of tert-butyl (E)-4-oxobut-2-enoate] proceeded in both cases under the dominant control of the lithium amide reagent. Subsequent diastereoselective enolate allylations installed the required stereogenic centres, and the pyrrolizidine ring system was rapidly accessed by a two-step protocol (viz. ozonolysis and one-pot hydrogenolysis/double reductive cyclisation), to complete the asymmetric syntheses of (?)-hastanecine, (?)-turneforcidine and (?)-platynecine in 17, 8 and 24% overall yield, respectively, in eleven steps from commercially available 2,2-dimethoxyacetaldehyde in each case.

The tandem cycloaddition chemistry of nitroalkenes. A novel synthesis of (-)-hastanecine

A short and efficient asymmetric synthesis of the pyrrolizidine necine base (-)-hastanecine is described. The key reaction in the synthesis is a sequential inter [4 + 2]/inter [3 + 2] cycloaddition. The Lewis acid promoted [4 + 2] cycloaddition between 2-

N-Acyliminium Ion Rearrangements: Generalities and Application to the Synthesis of Pyrrolizidine Alkaloids

N-Acyliminium ions of the 2-aza-1,5-hexadienyl type frequently rearrange to isomeric ions by a process which is formally a 2-aza-Cope rearrangement.When gem-dimethyl substitution is present at C-4 of the initially formed N-acyliminium ion, the rearranged