(2E,4E)-3-methyl-5-[6,6-dimethyl-2-(2-naphthylmethyl)cyclohex-1-enyl]-2,4-pentadienal | 1075731-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2E,4E)-3-methyl-5-[6,6-dimethyl-2-(2-naphthylmethyl)cyclohex-1-enyl]-2,4-pentadienal
• CAS: 1075731-42-8
• 化学式: C₂₅H₂₈O
• 分子量: 344.497
• InChiKey: JMWGVUCVTIPLTN-NIEGGPFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-3-methyl-5-[6,6-dimethyl-2-(2-naphthylmethyl)cyclohex-1-enyl]-2,4-pentadienal 、 triethyl 3-methyl-4-phosphonocrotonate 在 N,N-二甲基丙烯基脲 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以89%的产率得到ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-[6,6-dimethyl-2-(2-naphthylmethyl)cyclohex-1-enyl]-2,4,6,8-nonatetraenoate
  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
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 以664 mg的产率得到(2E,4E)-3-methyl-5-[6,6-dimethyl-2-(2-naphthylmethyl)cyclohex-1-enyl]-2,4-pentadienal
  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