(2E,4E,6Z,8E)-9-(2-butyl-6,6-dimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid | 1075731-60-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,4E,6Z,8E)-9-(2-butyl-6,6-dimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• CAS: 1075731-60-0
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: QZTGWEZSZARWSX-BNMLGCERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (2E,4E,6Z,8E)-9-(2-butyl-6,6-dimethylcyclohex-1-enyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到(2E,4E,6Z,8E)-9-(2-butyl-6,6-dimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
  参考文献：
  名称：

  Preparation and biological evaluation of 5-substituted retinoic acids

  摘要：

  Various 5-substituted retinoic acids were prepared by a palladium-catalyzed cross coupling reactions of vinyl nonaflates and E-or Z-3-tributylstannyl-2-beten-1-ol as a key reaction. These coupling products were then converted to the corresponding all-E-and 9Z-retinoic acid analogs via Horner -Emmons reaction and subsequent basic hydrolysis, and their biological activities were evaluated. The all-E-derivatives, 5-butyl and isobutyl analogs exhibited stronger effects for anti-proliferative and differentiation-inducing activities in HL-60 cells. In contrast, in 9Z-derivatives, none of the analogs showed any activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.025

文献信息

• Preparation and biological evaluation of 5-substituted retinoic acids
  作者：Akimori Wada、Naomi Matsuura、Yukari Mizuguchi、Kimie Nakagawa、Masayoshi Ito、Toshio Okano

  DOI：10.1016/j.bmc.2008.08.025

  日期：2008.9

  Various 5-substituted retinoic acids were prepared by a palladium-catalyzed cross coupling reactions of vinyl nonaflates and E-or Z-3-tributylstannyl-2-beten-1-ol as a key reaction. These coupling products were then converted to the corresponding all-E-and 9Z-retinoic acid analogs via Horner -Emmons reaction and subsequent basic hydrolysis, and their biological activities were evaluated. The all-E-derivatives, 5-butyl and isobutyl analogs exhibited stronger effects for anti-proliferative and differentiation-inducing activities in HL-60 cells. In contrast, in 9Z-derivatives, none of the analogs showed any activity. (C) 2008 Elsevier Ltd. All rights reserved.