167782-17-4

Basic information

• Product Name: methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hex-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate
• Synonyms: 3,5,9-undecatrienoic acid, 2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hex-1-yl]-4,10-dimethyl-11-oxo-, methyl ester, (2E,3E,5E,9E)-
• CAS NO: 167782-17-4
• Molecular Formula: C₂₁H₂₇NO₆
• Molecular Weight: 389.4422
• Mol File: 167782-17-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 628.9°C at 760 mmHg
• Flash Point: 334.1°C
• Density: 1.213g/cm³
• Vapor Pressure: 1.87E-18mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hex-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hex-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate(167782-17-4)
• EPA Substance Registry System: methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hex-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate(167782-17-4)

Safety Data

• Hazardous Substances Data: 167782-17-4(Hazardous Substances Data)

Upstream product

• 244273-41-4 (3E,5E,9E)-methyl [(2E)-ethylidene]-4,10-dimethyl-11-((1R,4S,5S)-4-methyl-2-oxo-3,6-dioxa-bicyclo[3.1.0]hex-1-yl)-11-oxo-undeca-3,5,9-trienoate 
• 244273-54-9 (1S,4S,5S)-4-methyl-1-[(2E,6E,8E,10E)-2,8-dimethyl-1-hydroxy-10-methoxycarbonyldodeca-2,6,10-trienyl]-3,6-dioxabicyclo[3.1.0]hexan-2-one 
• 244273-42-5 methyl (2E,3E,5E,9E)-2-ethylidene-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate 
• 244273-55-0 (1R,4S,5S)-4-methyl-1-trimethylsilyl-3,6-dioxabicyclo[3.1.0]hexan-2-one 
• 112775-69-6 (-)-(3S,4S,5S)-3,4-epoxy-5-methyldihydro-2(3H)-furanone 
• 92694-51-4 (S)-(+)-β-angelica lactone 
• 251358-67-5 (12R,13S,14S)-(3E,5E,9E)-methyl 12-carbamoyl-[(2E)-ethylidene]-14-hydroxy-4,10-dimethyl-11-oxo-12,13-epoxy-pentadeca-3,5,9-trienoate 
• 239108-30-6 methyl (3E,5E,9E)-11-<(2R,3S)-2-carbamoyl-3-<(R)-1-hydroxyethyl>oxiranyl>-4,10-dimethyl-2-<(E)-ethylidene>-11-oxoundeca-3,5,9-trienoate 
• 204378-77-8 di-tert-butyl 2-<(1S,2R)-1,2-propyl>-2-iodomalonate 
• 204378-89-2 di-tert-butyl 2-<(1R,2R)-1,2-propyl>malonate 
• 239100-56-2 N-methoxy-N-methyl (2S,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-carbamoyl-oxirane-2-carboxamide 
• 204378-78-9 di-tert-butyl (S)-3-<(R)-1-hydroxyethyl>oxirane-2,2-dicarboxylate 
• 204378-80-3 N-methoxy-N-methyl (1R,4R,5S)-4-methyl-2-oxo-3,6-dioxabicyclo<3.1.0>hexane-1-carboxamide 
• 204378-79-0 (1R,4R,5S)-4-methyl-2-oxo-3,6-dioxabicyclo<3.1.0>hexane-1-carboxylic acid 

Downstream Products

• 32381-28-5 N,N'-diacetyl-L-cystine dimethyl ester 
• 1038918-04-5 (2E,6E,8E,10E)-10-(methoxycarbonyl)-2,8-dimethyldodeca-2,6,8,10-tetraenoic acid 

Relevant articles and documents

Convergent total synthesis of epolactaene: Application of bridgehead oxiranyl anion strategy

Total synthesis of (+)-epolactaene was accomplished by a convergent approach utilizing the fluoride anion-catalyzed aldol-type reaction of (-)-α-trimethylsilylangelica lactone epoxide with tetraene aldehyde as a key reaction.

Diastereoselective total synthesis of both enantiomers of epolactaene

A stereocontrolled total synthesis of both the (+)- and (-)-epolactaene ((+)- and (-)-1) enantiomers from tetrahydropyran-2-ol is described. The following reactions in this synthesis are particularly noteworthy: (1) the stereoselective construction of the conjugated (E,E,E)-triene by a combination of kinetic deprotonation and thermodynamic equilibration, (2) the E-selective Knoevenagel condensation of β-ketonitrile 33 with a chiral 2-alkoxyaldehyde, (3) a diastereoselective epoxidation achieved using a bulky nucleophile (TrOOLi) and an appropriate protecting group, (4) the mild hydrolysis of an α-epoxy nitrile by silica gel on TLC facilitated by hydroxyl-mediated, intramolecular assistance.

Absolute Configuration and Total Synthesis of (+)-Epolactaene, a Neuritogenic Agent from Penicillium sp. BM 1689-P Active in Human Neuroblastoma Cells

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