538-90-9

Basic information

• Product Name: γ-coniceine
• Synonyms: γ-coniceine;(+)-ent-Coniceine;(8aS)-Octahydroindolizine;(8aα)-Octahydroindolizine;2-(1-Propenyl)piperidine;b-Coniceine
• CAS NO: 538-90-9
• Molecular Formula: C₈H₁₅N
• Molecular Weight: 125.214
• Mol File: 538-90-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 168.639°C at 760 mmHg
• Flash Point: 47.886°C
• Appearance: /
• Density: 0.905g/cm³
• Vapor Pressure: 1.603mmHg at 25°C
• Refractive Index: 1.521
• PKA: 10.12±0.10(Predicted)
• CAS DataBase Reference: γ-coniceine(CAS DataBase Reference)
• NIST Chemistry Reference: γ-coniceine(538-90-9)
• EPA Substance Registry System: γ-coniceine(538-90-9)

Safety Data

• Hazardous Substances Data: 538-90-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid with characteristic odor sim ilar to coniine; boils at 171°C (339.8°F); density 0.875 at 15°C (59°F); alkaline; slightlysoluble in water, dissolves readily in organicsolvents.

Uses

γ-Coniceine occurs in the seeds of poisonhemlock (Conium maculatum L. or Umbelliferae). It is produced by reduction ofconiine.

Health Hazard

Acute oral toxicity of γ-coniceine is greaterthan that of coniine. The symptoms are similar. Ingestion may cause drowsiness, nausea,vomiting, respiratory distress, convulsions,cyanosis, and at high doses, death. An oralLD50 value in mice is reported as 12 mg/kg(NIOSH 1986).

InChI:InChI=1/C8H15N/c1-2-5-8-6-3-4-7-9-8/h2,5,8-9H,3-4,6-7H2,1H3/b5-2-

Upstream product

• 495-20-5 (+)-conhydrine 
• 161009-85-4 5,6-octadienylamine 

Downstream Products

• 1255667-40-3 (E)-1-N-benzoyl-2-(prop-1-enyl)piperidine 

Relevant articles and documents

Constrained geometry organoactinides as versatile catalysts for the intramolecular hydroamination/cyclization of primary and secondary amines having diverse tethered C-C unsaturation

A series of "constrained geometry" organoactinide complexes, (CGC)An(NMe)2 (CGC = Me2-Si(η5-Me 4C5)(tBuN); An = Th, 1; U, 2), has been prepared via efficient in situ, two-step protodeamination routes in good yields and high purity. Both 1 and 2 are quantitatively converted to the neutrally charged, solvent-free dichlorides (1-Cl2, 2-Cl2) and slightly more soluble diiodides (1-I2, 2-I2) with excess Me3Si-X (X = Cl, I) in non-coordinating solvents. The new complexes were characterized by NMR spectroscopy, elemental analysis, and (for 1 and 2) single-crystal X-ray diffraction, revealing substantially increased metal coordinative unsaturation vs the corresponding Me2SiCp″ 2AnR2 (Cp″ = η5-Me4C 5; An = Th, R = CH2-(SiMe3), 3; An = U, R = CH2Ph, 4) and Cp′2AnR2 (Cp′ = η5-Me5C5 ; An = Th, R = CH 2(SiMe3), 5; An = U, R = CH2(SiMe3), 6) complexes. Complexes 1-6 exhibit broad applicability for the intramolecular hydroamination of diverse C-C unsaturations, including terminal and internal aminoalkenes (primary and secondary amines), aminoalkynes (primary and secondary amines), aminoallenes, and aminodienes. Large turnover frequencies (N t up to 3000 h-1) and high regioselectivities (≥95%) are observed throughout, along with moderate to high diastereoselectivities (up to 90% trans ring closures). With several noteworthy exceptions, reactivity trends track relative 5f ionic radii and ancillary ligand coordinative unsaturation. Reactivity patterns and activation parameters are consistent with a reaction pathway proceeding via turnover-limiting C=C/C=C insertion into the An-N σ-bond.