2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-cyclohept-1-enecarbaldehyde | 181303-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-cyclohept-1-enecarbaldehyde
• 英文别名: 2-[(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]cycloheptene-1-carbaldehyde
• CAS: 181303-15-1
• 化学式: C₁₉H₂₈O
• 分子量: 272.431
• InChiKey: WVUCIYAMHDZBES-VAWYXSNFSA-N

物化性质

• 沸点：
  399.0±21.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 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]-cyclohept-1-enecarbaldehyde 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]cyclohept-1-enyl]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：

  2-三氟甲基磺酰氧基-1-环庚烯-1-甲酸乙酯 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， 生成 2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-cyclohept-1-enecarbaldehyde
  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

• Novel retinoids
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0728742A2

  公开（公告）日：1996-08-28

  Novel nonatetraenoic acid derivatives of the formula wherein the dotted bond is optional and R1 and R2 are as defined in the specific ation selectively bind to retinoic acid X-receptors (RXR) have anti-acne acitvity and potentiate the activity of retinoids having RARα activity.

  式中的新型非四烯酸衍生物 其中，虚线键为任选键，R1 和 R2 如在具体说明中所定义，选择性地与维甲酸 X 受体 (RXR) 结合，具有抗痤疮活性，并能增强具有 RARα 活性的维甲酸的活性。
• US5986131A
  申请人：——

  公开号：US5986131A

  公开（公告）日：1999-11-16
• 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.