2-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl]cyclohex-1-ene-carbaldehyde | 454194-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl]cyclohex-1-ene-carbaldehyde
• 英文别名: 2-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]cyclohexene-1-carbaldehyde
• CAS: 454194-38-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: ZWUKBRSXASGSCX-HRCSPUOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl]cyclohex-1-ene-carbaldehyde 在 manganese(IV) oxide 、 sodium chlorite 、 正丁基锂 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 30.0h， 生成 (2E,4E)-3-methyl-5-{2-[(E)-2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethenyl]-1-cyclohexen-1-yl}-2,4-pentadienoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Annular 9-cis-Retinoids and Binding Characterization to the Retinoid X Receptor

  摘要：

  Analogues of 9-cis-retinoic acid incorporating an alicyclic ring between the C19 and C10 positions have been synthesized and evaluated as ligands for the RXRalpha nuclear receptor. The stereocontrolled synthesis of these configurationally constrained retinoids combines a Stille cross-coupling and the Wittig reaction as key bond-forming steps. The palladium-catalyzed cross-coupling reaction of the beta-bromo-alpha,beta-unsaturated aldehydes 5 to dienylstannane 6 is very fast at room temperature, and takes place with preservation of the dienylstannane geometry. A highly stereoselective Wittig reaction afforded the C7-C8 bond connecting the hydrophobic ring to the retinoid side chain. The binding affinities of these compounds for the receptor were determined, and the structural and energetic rationale behind the affinity profile of the cyclic 9-cis-retinoic acid derivatives for the RXRalpha nuclear receptor was characterized by using Molecular Mechanics protocols.

  DOI：

  10.1021/jo0257391
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 、 2,4-戊二烯-1-醇,3-甲基-5-(三丁基甲锡烷基)-,(2E,4E)- 在 tris(dibenzylideneacetone)dipalladium (0) N-甲基吡咯烷酮 、 三苯胂 作用下， 反应 0.08h， 以97%的产率得到2-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl]cyclohex-1-ene-carbaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis of Annular 9-cis-Retinoids and Binding Characterization to the Retinoid X Receptor

  摘要：

  Analogues of 9-cis-retinoic acid incorporating an alicyclic ring between the C19 and C10 positions have been synthesized and evaluated as ligands for the RXRalpha nuclear receptor. The stereocontrolled synthesis of these configurationally constrained retinoids combines a Stille cross-coupling and the Wittig reaction as key bond-forming steps. The palladium-catalyzed cross-coupling reaction of the beta-bromo-alpha,beta-unsaturated aldehydes 5 to dienylstannane 6 is very fast at room temperature, and takes place with preservation of the dienylstannane geometry. A highly stereoselective Wittig reaction afforded the C7-C8 bond connecting the hydrophobic ring to the retinoid side chain. The binding affinities of these compounds for the receptor were determined, and the structural and energetic rationale behind the affinity profile of the cyclic 9-cis-retinoic acid derivatives for the RXRalpha nuclear receptor was characterized by using Molecular Mechanics protocols.

  DOI：

  10.1021/jo0257391

文献信息

• Stereoselective Synthesis of Annular 9-<i>cis</i>-Retinoids and Binding Characterization to the Retinoid X Receptor
  作者：M. Paz Otero、Alicia Torrado、Yolanda Pazos、Fredy Sussman、Angel R. de Lera

  DOI：10.1021/jo0257391

  日期：2002.8.1

  Analogues of 9-cis-retinoic acid incorporating an alicyclic ring between the C19 and C10 positions have been synthesized and evaluated as ligands for the RXRalpha nuclear receptor. The stereocontrolled synthesis of these configurationally constrained retinoids combines a Stille cross-coupling and the Wittig reaction as key bond-forming steps. The palladium-catalyzed cross-coupling reaction of the beta-bromo-alpha,beta-unsaturated aldehydes 5 to dienylstannane 6 is very fast at room temperature, and takes place with preservation of the dienylstannane geometry. A highly stereoselective Wittig reaction afforded the C7-C8 bond connecting the hydrophobic ring to the retinoid side chain. The binding affinities of these compounds for the receptor were determined, and the structural and energetic rationale behind the affinity profile of the cyclic 9-cis-retinoic acid derivatives for the RXRalpha nuclear receptor was characterized by using Molecular Mechanics protocols.