160084-07-1

Basic information

• Product Name: Phosphoric acid diethyl ester 1-methylene-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl ester
• Synonyms: Phosphoric acid diethyl ester 1-methylene-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl ester
• CAS NO: 160084-07-1
• Molecular Weight: 330.404
• Mol File: 160084-07-1.mol

Chemical Properties

• CAS DataBase Reference: Phosphoric acid diethyl ester 1-methylene-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid diethyl ester 1-methylene-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl ester(160084-07-1)
• EPA Substance Registry System: Phosphoric acid diethyl ester 1-methylene-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl ester(160084-07-1)

Safety Data

• Hazardous Substances Data: 160084-07-1(Hazardous Substances Data)

Upstream product

• 82798-13-8 Triethyl-[(E)-1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propenyloxy]-silane 
• 79-77-6 (E)-β-ionone 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 18665-81-1 (E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-en-1-ol 
• 160084-16-2 2-<(2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-3-<(tert-butyldimethylsilyloxy)methyl>-2,6-nonadienyl>-2-<2-trimethylsilylfuran-4-yl>-1,3-dithian 
• 160084-13-9 (2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-3-<(tert-butyldimethylsilyloxy)methyl>-1-(N,N-di-n-butylamino)-2,6-nonadiene 
• 160084-18-4 2-trimethylsilyl-4-<(2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-4-hydroxymethyl-1-hydroxy-2,6-nonadien-1-yl>-furan 
• 160084-14-0 tert-Butyl-[(E)-2-[2-chloro-eth-(E)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-oct-5-enyloxy]-dimethyl-silane 
• 160084-12-8 (2E,6E)-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-7-methyl-3-hydroxymethyl-1-(N,N-di-n-butylamino)-2,6-nonadiene 
• 110202-09-0 1-bromo-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)-3-hexene 
• 110202-07-8 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 110202-12-5 2-trimethylsilyl-4-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-formyl-1-hydroxy-3,7-decadien-1-yl>-furan 
• 36772-04-0 1-(3-Butynyl)-2,6,6-trimethyl-1-cyclohexene 

Relevant articles and documents

Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement

An enantiospecific synthesis of the phospholipase A2 inhibitor (+)-(4R)-manoalide is reported in which all 25 carbons of the sesterterpenoid skeleton are constructed from 3-furaldehyde, trimethylalane, oxirane, CO, β-ionone, and propargyl bromide. The overall yield for the longest linear sequence (12 steps) is 12%. Key steps include (a) a zirconium-catalyzed carboalumination reaction to construct the C10-C11 trisubstituted alkene, (b) a Cu(I)-mediated 1,2-metalate rearrangement to construct the C6-C7 trisubstituted alkene, (c) a Sharpless kinetic resolution to secure the (4R)-stereochemistry, (d) generation of a 5-stannyl-2,3-dihydrofuran by Mo-catalyzed cycloisomerization of a homopropargylic alcohol, and (e) construction of the hydroxyfuranone ring by photooxidation of a silylfuran.

Two Syntheses of Manoalide via Heteroatom-Assisted Alkyne Carbometallation

Two approaches to the sesterterpenoid phospholipase A2 inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene.Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted 5-hydroxy-2(5H)-furanone moiety.