(E)-3-[2-[(4-methylphenyl)methyl]-1,3-dioxoisoindol-5-yl]prop-2-enoic acid | 930296-19-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-[2-[(4-methylphenyl)methyl]-1,3-dioxoisoindol-5-yl]prop-2-enoic acid
• CAS: 930296-19-8
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: CXULIJWEPIQDGA-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-[2-[(4-methylphenyl)methyl]-1,3-dioxoisoindol-5-yl]prop-2-enoic acid 在 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-N-hydroxy-3-[2-[(4-methylphenyl)methyl]-1,3-dioxoisoindol-5-yl]prop-2-enamide
  参考文献：
  名称：

  Design and synthesis of phthalimide-type histone deacetylase inhibitors

  摘要：

  Several hydroxamic acid derivatives with a substituted phthalimicle group as a linker and/or cap structure, prepared during structural development studies based on thalidomide, were found to have historic deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that nature of the substituent introduced at the phthalimide nitrogen atom, introduction of a hydroxamic acid structure, and distance between the N-hydroxyl group and the cap structure are important for HDAC-inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.048
• 作为产物：
  描述：

  5-Hydroxy-2-[(4-methylphenyl)methyl]isoindole-1,3-dione 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (E)-3-[2-[(4-methylphenyl)methyl]-1,3-dioxoisoindol-5-yl]prop-2-enoic acid
  参考文献：
  名称：

  Design and synthesis of phthalimide-type histone deacetylase inhibitors

  摘要：

  Several hydroxamic acid derivatives with a substituted phthalimicle group as a linker and/or cap structure, prepared during structural development studies based on thalidomide, were found to have historic deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that nature of the substituent introduced at the phthalimide nitrogen atom, introduction of a hydroxamic acid structure, and distance between the N-hydroxyl group and the cap structure are important for HDAC-inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.048