36772-04-0

Basic information

• Product Name: 1-(3-Butynyl)-2,6,6-trimethyl-1-cyclohexene
• Synonyms: 1-(3-Butynyl)-2,6,6-trimethyl-1-cyclohexene
• CAS NO: 36772-04-0
• Molecular Weight: 176.302
• Mol File: 36772-04-0.mol

Chemical Properties

• CAS DataBase Reference: 1-(3-Butynyl)-2,6,6-trimethyl-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Butynyl)-2,6,6-trimethyl-1-cyclohexene(36772-04-0)
• EPA Substance Registry System: 1-(3-Butynyl)-2,6,6-trimethyl-1-cyclohexene(36772-04-0)

Safety Data

• Hazardous Substances Data: 36772-04-0(Hazardous Substances Data)

Upstream product

• 160084-07-1 Phosphoric acid diethyl ester 1-methylene-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propyl ester 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 82798-13-8 Triethyl-[(E)-1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-propenyloxy]-silane 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 79-77-6 (E)-β-ionone 
• 31499-72-6 7,8-dihydro-α-ionone 

Downstream Products

• 110202-07-8 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 74133-09-8 (E)-2-(4-iodo-3-methylbut-3-en-1-yl)-1,3,3-trimethylcyclohex-1-ene 
• 18665-81-1 (E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-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 
• 110202-09-0 1-bromo-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)-3-hexene 
• 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 
• 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 
• 160084-18-4 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 
• 160084-13-9 (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 
• 160084-16-2 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 
• 74133-10-1 2-((3E,7E)-8-Iodo-3,7-dimethyl-octa-3,7-dienyl)-1,3,3-trimethyl-cyclohexene 
• 74133-11-2 1,3,3-Trimethyl-2-((E)-3-methyl-oct-3-en-7-ynyl)-cyclohexene 
• 74133-12-3 2-((3E,7E)-3,7-Dimethyl-dodeca-3,7-dien-11-ynyl)-1,3,3-trimethyl-cyclohexene 

Relevant articles and documents

Bidirectional Hiyama–Denmark Cross-Coupling Reactions of Bissilyldeca-1,3,5,7,9-pentaenes for the Synthesis of Symmetrical and Non-Symmetrical Carotenoids

The construction of the carotenoid skeleton by Pd-catalyzed Csp2?Csp2 cross-coupling reactions of symmetrical and non-symmetrical 1,10-bissilyldeca-1,3,5,7,9-pentaenes and the corresponding complementary alkenyl iodides has been developed. Reaction conditions for these bidirectional and orthogonal Hiyama–Denmark cross-coupling reactions of bisfunctionalized pentaenes are mild and the carotenoid products preserve the stereochemical information of the corresponding oligoene partners. The carotenoids synthesized in this manner include β,β-carotene and (3R,3′R)-zeaxanthin (symmetrical) as well as 9-cis-β,β-carotene, 7,8-dihydro-β,β-carotene and β-cryptoxanthin (non-symmetrical).

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.