ethyl 9Z-13-demethylretinoate | 757240-62-3

• 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: ethyl 9Z-13-demethylretinoate
• CAS: 757240-62-3
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: BNCXNZKXIXUNMU-ZVVAFJOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 9Z-13-demethylretinoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以73%的产率得到2,4,6,8-壬四烯酸,7-甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-,(2E,4E,6Z,8E)-
  参考文献：
  名称：

  Preparation and biological activity of 13-substituted retinoic acids

  摘要：

  13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.047
• 作为产物：
  描述：

  (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 正丁基锂 、 三苯胂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 ethyl 9Z-13-demethylretinoate
  参考文献：
  名称：

  Preparation and biological activity of 13-substituted retinoic acids

  摘要：

  13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.047