189633-82-7

Basic information

• Product Name: Cyclohexanone, 2,2,6-trimethyl-, hydrazone
• CAS NO: 189633-82-7
• Molecular Formula: C9H18N2
• Molecular Weight: 154.255
• Mol File: 189633-82-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 2,2,6-trimethyl-, hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2,2,6-trimethyl-, hydrazone(189633-82-7)
• EPA Substance Registry System: Cyclohexanone, 2,2,6-trimethyl-, hydrazone(189633-82-7)

Safety Data

• Hazardous Substances Data: 189633-82-7(Hazardous Substances Data)

Upstream product

• 2816-57-1 2,6-dimethylcyclohexanone 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 

Downstream Products

• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 471-90-9 2,6,6-trimethyl-cyclohex-1-enecarboxylic acid 
• 84518-22-9 2‐methyl‐4‐(2,6,6‐trimethylcyclohex‐1‐en‐1‐yl)butanal 
• 101679-28-1 1,3,3-trimethylcyclohexenyl chloride 
• 1453111-19-7 C₉H₁₆Br₂ 
• 1453111-17-5 1,1-dichloro-2,2,6-trimethylcyclohexane 
• 1453111-14-2 2-trimethylsilyl-1,3,3-trimethylcyclohexene 
• 123347-40-0 2-bromo-1,3,3-trimethylcyclohexene 
• 3917-40-6 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol 
• 54226-17-4 (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal 
• 86708-67-0 ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 302-79-4 9-cis-retinoic acid 
• 54345-61-8 α,2,6,6-tetramethyl-1-cyclohexene-1-methanol 
• 1197-92-8 1-(2,6,6-trimethyl-cyclohex-1-enyl)-ethanone 

Relevant articles and documents

Relay-Heck Cross-Coupling Between Alkenyl Halides and Unsaturated Alcohols in the Synthesis of Open-Chain Analogues of Musk Odorant Vulcanolide

Unactivated alkenyl iodides and bromides underwent an unprecedented palladium-catalyzed relay-Heck cross-coupling with a whole range of alkenols of different chain lengths linking the alkene and the alcohol, affording unsaturated aldehydes and ketones in moderate to good yields. In contrast, alkenyl triflates were not suitable partners for this reaction. This method allowed the preparation of open-chain analogues of the musk odorant Vulcanolide, several of which retained key olfactory properties of the parent molecule.

Total synthesis of (±)-hedychenone: Trimethyldecalin terpene systems via stepwise allenoate diene cycloaddition

(Diagram presented) The total synthesis of hedychenone 1 is described. The cycloaddition of the hindered diene 2 and the allenecarboxylate 3 has been shown conclusively to proceed via the [2+2] cycloadduct 5 to give a 2:1 mixture of the desired formal Diels-Alder adducts, the exo and endo isomers 4xn and is thus a stepwise [4+2] cycloaddition. The exo isomer 4x was converted in four steps (reduction, oxidation, olefination, and desilylation) into hedychenone 1.

Stereoselective synthesis of 9-cis-retinoic acid by Suzuki reaction

The entire polyenic side chain of ethyl 9-cis-retinoate (7) has been stereoselectively synthesized and attached to the hydrophobic ring by a high-yielding thallium-accelerated Suzuki cross-coupling reaction. The Suzuki reaction partners, tetraenyl iodide 18 and alkenyl organoborane 19, are more conveniently used immediately after generation from their precursors. Alternative approaches using either the Stille reaction or a Suzuki reaction with a shorter polyenic component proved less efficient. The highly convergent sequence can be adapted to the preparation of analogs of 9-cis-retinoic acid (2), the natural ligand for the retinoid X (RXR) subfamily of nuclear receptors.