ethyl (2E,4E,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hepta-2,4-dienoate | 596093-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2E,4E,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hepta-2,4-dienoate
• CAS: 596093-46-8
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: XCVWSOHAONQBRX-YEFLIOATSA-N

物化性质

• 沸点：
  383.0±35.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2E,4E,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hepta-2,4-dienoate 在 N-甲基吗啉 、 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氟乙酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 N-((2E,4E)-(R)-5-Benzyloxycarbamoyl-1-methyl-penta-2,4-dienyl)-4-dimethylamino-benzamide
  参考文献：
  名称：

  Amide analogues of TSA: synthesis, binding mode analysis and HDAC inhibition

  摘要：

  The synthesis of new amide type historic deacetylase inhibitors is described, having an (R)-methyl substituent and a diene or saturated structure of the chain linking the hydroxamic acid and dimethylaminobenzoyl groups. The saturated compound shows stronger HDAC inhibition than the unsaturated analogue. Molecular modeling suggests that the flexibility of the linker chain is important for an optimal orientation of the dimethylaminobenzoyl group in the enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00284-1
• 作为产物：
  描述：

  (R)-1-(甲氧基(甲基)氨基)-1-氧代-2-丙基氨基甲酸叔丁酯 在 lithium hydroxide 、 lithium aluminium tetrahydride 作用下， 生成 ethyl (2E,4E,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hepta-2,4-dienoate
  参考文献：
  名称：

  Amide analogues of TSA: synthesis, binding mode analysis and HDAC inhibition

  摘要：

  The synthesis of new amide type historic deacetylase inhibitors is described, having an (R)-methyl substituent and a diene or saturated structure of the chain linking the hydroxamic acid and dimethylaminobenzoyl groups. The saturated compound shows stronger HDAC inhibition than the unsaturated analogue. Molecular modeling suggests that the flexibility of the linker chain is important for an optimal orientation of the dimethylaminobenzoyl group in the enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00284-1

文献信息

• Amide analogues of TSA: synthesis, binding mode analysis and HDAC inhibition
  作者：K Van Ommeslaeghe、G Elaut、V Brecx、P Papeleu、K Iterbeke、P Geerlings、D Tourwé、V Rogiers

  DOI：10.1016/s0960-894x(03)00284-1

  日期：2003.6

  The synthesis of new amide type historic deacetylase inhibitors is described, having an (R)-methyl substituent and a diene or saturated structure of the chain linking the hydroxamic acid and dimethylaminobenzoyl groups. The saturated compound shows stronger HDAC inhibition than the unsaturated analogue. Molecular modeling suggests that the flexibility of the linker chain is important for an optimal orientation of the dimethylaminobenzoyl group in the enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.