2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-benzaldehyde | 189272-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-benzaldehyde
• 英文别名: 2-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]benzaldehyde
• CAS: 189272-46-6
• 化学式: C₁₈H₂₂O
• 分子量: 254.372
• InChiKey: OSYIGSMOXDUPTP-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-benzaldehyde 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 生成 (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]phenyl]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 manganese(IV) oxide 、 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 、 Petroleum ether 、 苯 为溶剂， 反应 2.0h， 生成 2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-benzaldehyde
  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

文献信息

• Stereoselective synthesis and receptor activity of conformationally defined retinoid X receptor selective ligands
  作者：Vidyasagar Vuligonda、Michael E. Garst、Roshantha A.S. Chandraratna

  DOI：10.1016/s0960-894x(99)00048-7

  日期：1999.2

  Retinoid X Receptor (RXR) specific ligands are currently being investigated for the treatment of metabolic diseases such as type II diabetes. We report the synthesis of conformationally locked retinoids, which are potent RXR selective ligands, and the attempted synthesis of 9-cyclopropyl locked analogs of RA and 9-cis RA. (C) 1999 Elsevier Science Ltd. All rights reserved.
• US7655699B1
  申请人：——

  公开号：US7655699B1

  公开（公告）日：2010-02-02
• Thrombomodulin induction in cultured human endothelial cells by 9-cis-locked retinoic acid analogues
  作者：Shiro Ikegami、Takamasa Iimori、Minoru Sudo、Maroka Kitsukawa、Alireza Foroumadi、Takeshi Yonemura、Hideyo Takahashi、Keiichiro Kizaki、Hidemi Ishii

  DOI：10.1016/j.bmc.2006.04.043

  日期：2006.8

  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.