1892-05-3

Basic information

• Product Name: Cyclohexene, 2-ethynyl-1,3,3-trimethyl-
• CAS NO: 1892-05-3
• Molecular Formula: C11H16
• Molecular Weight: 148.248
• Mol File: 1892-05-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexene, 2-ethynyl-1,3,3-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexene, 2-ethynyl-1,3,3-trimethyl-(1892-05-3)
• EPA Substance Registry System: Cyclohexene, 2-ethynyl-1,3,3-trimethyl-(1892-05-3)

Safety Data

• Hazardous Substances Data: 1892-05-3(Hazardous Substances Data)

Upstream product

• 41613-59-6 1-ethynyl-2,2,6-trimethyl-1-cyclohexanol 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 87570-48-7 acetic acid-(1-ethynyl-2,2,6-trimethyl-cyclohexyl ester) 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 79-77-6 (E)-β-ionone 
• 26005-41-4 1-ethynyl-2,6,6-trimethylcyclohexanol 
• 59637-36-4 2-chlorovinylidene-1,1,3-trimethyl-cyclohexane 

Downstream Products

• 103633-78-9 5-(2,6,6-Trimethyl-cyclohex-1-enyl)-penta-2,4-diyn-1-ol 
• 104257-78-5 N-methyl-N-<3-(2,6,6-trimethyl-1-cyclohexenyl)-2-propinyl>-1-naphthalinmethanamin 
• 3917-40-6 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol 
• 137047-34-8 (Z)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-en-4-yn-1-ol 
• 93156-22-0 3-Cyclopropyl-1-(2,6,6-trimethylcyclohex-1-enyl)-but-1-in-3-ol 
• 15356-74-8 (+/-)-dihydroactinidiolide 
• 163313-86-8 Ethyl 6-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethynyl]-2-naphthoate 
• 1974-90-9 (+/-)-<1-Methyl-3-(2.6.6-trimethyl-cyclohex-1-enyl)-prop-2-inyl>-malonsaeure 
• 1462-21-1 (+/-)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-4-insaeure 
• 334826-81-2 (E)-3-phenyl-1-(2,6,6-trimethylcyclohex-1-enyl)prop-2-en-1-one 
• 54345-61-8 α,2,6,6-tetramethyl-1-cyclohexene-1-methanol 

Relevant articles and documents

Synthetic Access to Noncanonical Strigolactones: Syntheses of Carlactonic Acid and Methyl Carlactonoate

Strigolactones are plant hormones regulating essential stages of a plant's development. Their low natural abundance combined with a low chemical stability significantly hampered the detailed investigation of their biological activity. Noncanonical strigolactones lack the fused tricyclic ABC-ring system commonly present in canonical-type strigolactones but feature an open-chain unit linking structurally diverse A-ring moieties to the butenolide D-ring. We herein present an efficient synthetic access to enantiomerically pure noncanonical strigolactones by a Stille cross-coupling approach to forge the central diene moiety and demonstrate this strategy by syntheses of natural products methyl carlactonoate and carlactonic acid. Furthermore, a synthetic access to deuterium-labeled analogues of these natural products has been developed.

Synthesis of the 2-alkenyl-4-alkylidenebut-2-eno-4-lactone (=α-alkenyl-γ-alkylidenebutenolide) core structure of the carotenoid pyrrhoxanthin via the regioselective dihydroxylation of hepta-2,4-diene-5-ynoic acid esters

A new strategy for the stereoselective synthesis of 4-alkylidenebut-2-eno- 4-lactones (= γ-alkylidenebutenolides) with (Z)-configuration of the exocyclic C=C bond at C(4) was developed. It is exemplified by the synthesis of 4-alkylidenebutenolactone 31 (Scheme 4), which constitutes a substructure of the carotenoids pyrrhoxanthin (1) and peridinin. The formation of the precursor 4-(1-hydroxyalkyl)butenolactone 29 was accomplished either by cyclocarbonylation of the prop-2-yn-1-ol moiety of 27 (→ 29) or by hydrostannylation of the isopropylidene-protected alkynoic acid ester 26 (->28) followed by transacetalization/transesterification (→ 30). The 4- alkylidenebutenolactone was formed by the ami-selective Mitsunobu dehydration 29 → 31.

HIGHLY STEREOSELECTIVE AND GENERAL SYNTHESIS OF (Z)-3-METHYL-2-ALKEN-1-OLS VIA PALLADIUM-CATALYZED CROSS COUPLING OF (Z)-3-IODO-2-BUTEN-1-OL WITH ORGANOZINCS AND OTHER ORGANOMETALS

The reaction of Zn-protected (Z)-3-iodo-2-buten-1-ol with organozincs in the presence of 1-5 mol percent of a Pd complex, e.g., Pd(PPh3)4 or Cl2Pd(PPh3)2 and n-BuLi (2 equiv), in DMF provides a highly stereoselective (>/= 96 percent), general, and high-yi