methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophen-3-yl]penta-2,4-dienoate | 189272-35-3

• 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: methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophen-3-yl]penta-2,4-dienoate
• CAS: 189272-35-3
• 化学式: C₂₂H₃₀O₂S
• 分子量: 358.545
• InChiKey: MBFLSJSKHVYGNS-WJXYHLTCSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  494.2±38.0 °C(predicted)
• 密度：
  1.141±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophen-3-yl]penta-2,4-dienoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以96%的产率得到(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：

  4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophene-3-methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrothiophen-3-yl]penta-2,4-dienoate
  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