(2Z,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dien-1-ol | 162212-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2Z,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dien-1-ol
• CAS: 162212-15-9
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: ZMKLXPKLLQZZCX-OHFYBLQUSA-N

物化性质

• 沸点：
  388.5±42.0 °C(predicted)
• 密度：
  0.91±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.16
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dien-1-ol 在 chromium(VI) oxide 、 Amberlist A-26 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-but-3-en-2-one 、 (2Z,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dienal 、 (2E,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dienal
  参考文献：
  名称：

  Synthesis of some retinoids bearing different heterocyclic rings with anticancer activity

  摘要：

  The synthesis of a series of pyrrole and imidazole retinoids is reported. The compounds were obtained by means of reactions of phosphoranes or phosphonates with aldehydes. Several of these retinoids were evaluated against different tumor systems and some were found to have an activity comparable to that of all-trans retinoic acid.

  DOI：

  10.1016/0223-5234(94)90136-8
• 作为产物：
  描述：

  (2Z,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dienoic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以100%的产率得到(2Z,4E)-5-(4-Ethynyl-1,3,5-trimethyl-1H-pyrrol-2-yl)-3-methyl-penta-2,4-dien-1-ol
  参考文献：
  名称：

  Synthesis of some retinoids bearing different heterocyclic rings with anticancer activity

  摘要：

  The synthesis of a series of pyrrole and imidazole retinoids is reported. The compounds were obtained by means of reactions of phosphoranes or phosphonates with aldehydes. Several of these retinoids were evaluated against different tumor systems and some were found to have an activity comparable to that of all-trans retinoic acid.

  DOI：

  10.1016/0223-5234(94)90136-8