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

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

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

Downstream Products

• 189633-81-6 2‐iodo‐1,3,3‐trimethylcyclohex‐1‐ene 
• 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 
• 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 
• 919103-36-9 ethyl (+/-)-2-{3-[1,1-dimethylethyl(dimethyl)silyloxy]-3-(2,6,6-trimethyl-1-cyclohexenyl)cyclobutylidene}acetate 
• 919103-34-7 1-[1,1-dimethylethyl(dimethyl)silyloxy]ethenyl-2,6,6-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 
• 101679-28-1 1,3,3-trimethylcyclohexenyl chloride 
• 1453111-19-7 C₉H₁₆Br₂ 

Relevant articles and documents

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

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The suzuki coupling reaction in the stereocontrolled synthesis of 9-cis-retinoic acid and its ring-demethylated analogues

The thallium-accelerated Suzuki coupling reaction of tetraenyl iodide 19 and cyclohexenyl boronate 18 afforded ethyl 9-cis-retinoate (12) in high yield. Both coupling partners of the Suzuki reaction are better reacted immediately after generation from their precursors, tetraenylstannane 10 and cyclohexenyl iodide 13. The geometrically homogeneous tetraenylstannane 10, comprising the polyenic side chain of ethyl 9-cis-retinoate and its ring-demethylated analogues, was synthesized by a stereoselective Horner - Wadsworth - Emmons reaction. On the other hand, easily available cyclohexanones are ideal starting materials for preparation of the cyclohexenyl boronates required for the synthesis of the ring-modified 9-cis-retinoic acid analogues. For hindered cyclohexanones, hydrazones were converted to cyclohexenyl iodides. Iodine - lithium exchange and trapping with B(OMe)3 then afforded the cyclohexenyl boronates. If the precursor cyclohexanone has secondary carbons, the alkenyllithium species was conveniently formed by elimination of the C,N-dilithiated intermediate obtained upon treating the trisylhydrazone with n-BuLi (Shapiro reaction). None of the above procedures allowed the generation of the more substituted organolithium from 2-methylcyclohexanone. However, the alternative Stille cross-coupling of 34 and 10 afforded 9-cis-1,1-bisdemethylretinoic acid 7. Both Suzuki and Stille coupling reactions took place under mild conditions, and the preservation of the retinoid side-chain geometry was therefore secured.

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.