119233-01-1

Basic information

• Product Name: Methyl-diphenyl-((2E,4Z)-4-trimethylsilanylmethyl-hexa-2,4-dienyl)-phosphonium; iodide
• CAS NO: 119233-01-1
• Molecular Weight: 494.471
• Mol File: 119233-01-1.mol

Chemical Properties

• CAS DataBase Reference: Methyl-diphenyl-((2E,4Z)-4-trimethylsilanylmethyl-hexa-2,4-dienyl)-phosphonium; iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-diphenyl-((2E,4Z)-4-trimethylsilanylmethyl-hexa-2,4-dienyl)-phosphonium; iodide(119233-01-1)
• EPA Substance Registry System: Methyl-diphenyl-((2E,4Z)-4-trimethylsilanylmethyl-hexa-2,4-dienyl)-phosphonium; iodide(119233-01-1)

Safety Data

• Hazardous Substances Data: 119233-01-1(Hazardous Substances Data)

Upstream product

• 74-88-4 methyl iodide 
• 119233-00-0 Phosphoric acid diethyl ester (2E,4Z)-4-trimethylsilanylmethyl-hexa-2,4-dienyl ester 
• 65567-06-8 lithium diphenylphosphide 

Relevant articles and documents

Synthesis of the 11-Membered Cytochalasin Ring System By Modified Reformatsky Cyclization

Zn or SmI2 cause cyclization of 7 to 8 which can be taken on to the cytochalasan 13.

A Synthesis of C(16),C(18)-Bis-epi-cytochalasin D via Reformatsky Cyclization

Triene 5 has been prepared by the E-selective olefination of aldehyde 12 with the ylide 11. Several alternative syntheses of 12 were evaluated, and the successful route involved conversion of 22 into the vinyl ether 23 by Petasis olefination, followed by Claisen rearrangement. Diels-Alder cycloaddition of 5 with 4 gave the adduct 6 in 77% yield, and Reformatsky cyclization under dilution conditions afforded 10 (67%). After conversion to enol silane 32, oxidation with dimethyldioxirane produced 34. Conversion to a key intermediate 38 using electrophilic selenenylation and selenoxide rearrangement, followed by enolate alkylation and deprotection, gave 43. The X-ray crystal structure of 43 was determined to prove the stereochemistry.