4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophene-3-methanol | 189272-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophene-3-methanol
• CAS: 189272-05-7
• 化学式: C₁₆H₂₄OS
• 分子量: 264.432
• InChiKey: GZWWFTPWHRAWAT-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophene-3-methanol 在 氢氧化钾 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 (2E,4E)-3-methyl-5-[4-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]-2,5-dihydrothiophen-3-yl]penta-2,4-dienoic acid
  参考文献：
  名称：

  Thrombomodulin induction in cultured human endothelial cells by 9-cis-locked retinoic acid analogues

  摘要：

  9-cis-Retinoic acid (RA) analogues devised to lock the 9-cis double bond by ring formation were synthesized using two stereoselective carbon-carbon bond formation reactions as key steps. The palladium-mediated Suzuki reaction was adopted to construct a 7E-double bond (RA numbering) and the Horner-Emmons olefination was employed for stereoselective 11E-double bond (RA numbering) formation. The synthesized 9-cis-RA analogues that are locked by five-membered ring systems (cyclopentene, dihydrofuran, and dihydrothiophene) were shown to have comparable thrombomodulin induction activities to that of 9-cis RA. Conformational analysis of these compounds showed their similarity to 9-cis RA in the spatial orientation of the side chain and the terminal carboxy group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.043
• 作为产物：
  描述：

  2-(1-ethynyl-2,6,6-trimethylcyclohexene)-1,3,2-benzodioxaborole 在 四(三苯基膦)钯 氢氧化钾 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophene-3-methanol
  参考文献：
  名称：

  Thrombomodulin induction in cultured human endothelial cells by 9-cis-locked retinoic acid analogues

  摘要：

  9-cis-Retinoic acid (RA) analogues devised to lock the 9-cis double bond by ring formation were synthesized using two stereoselective carbon-carbon bond formation reactions as key steps. The palladium-mediated Suzuki reaction was adopted to construct a 7E-double bond (RA numbering) and the Horner-Emmons olefination was employed for stereoselective 11E-double bond (RA numbering) formation. The synthesized 9-cis-RA analogues that are locked by five-membered ring systems (cyclopentene, dihydrofuran, and dihydrothiophene) were shown to have comparable thrombomodulin induction activities to that of 9-cis RA. Conformational analysis of these compounds showed their similarity to 9-cis RA in the spatial orientation of the side chain and the terminal carboxy group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.043