methyl (Z)-2-azido-3-(5-bromo-2-heptan-2-yloxyphenyl)prop-2-enoate | 102651-62-7

• 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: methyl (Z)-2-azido-3-(5-bromo-2-heptan-2-yloxyphenyl)prop-2-enoate
• CAS: 102651-62-7
• 化学式: C₁₇H₂₂BrN₃O₃
• 分子量: 396.284
• InChiKey: KKFSPCDOQYYZTK-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-azido-3-(5-bromo-2-heptan-2-yloxyphenyl)prop-2-enoate 以 xylene 为溶剂， 生成 2-carbomethoxy-4-(2-heptyloxy)-7-bromoindole
  参考文献：
  名称：

  Synthesis and analgesic evaluation of 4-(2-heptyloxy)-7-[(Z)-(3-hydroxycyclohexyl)]indole: a caveat on indole-phenol bioisosterism

  摘要：

  The synthesis of 4-(2-heptyloxy)-7-[(Z)-(3-hydroxycyclohexyl)]indole (7) is described. Compound 7 was tested for analgesic properties in the phenylbenzoquinone writhing test and was found to be essentially devoid of activity. In contrast, cis-3-[4-(2-heptyloxy)-2-hydroxyphenyl]cyclohexanol (8), the analogue in which the pyrrolo ring is replaced by a hydroxyl group, had an ED50 of 8.3 mg/kg, sc, in the same model. The absence of bioisosterism between the pyrrolo ring and the phenolic hydroxyl group, in this instance, is discussed in terms of the circumstances that control the manifestation of bioisofunctionality between a pyrrolo ring and a phenolic hydroxyl group, which functions as a hydrogen-bond donor.

  DOI：

  10.1021/jm00158a023
• 作为产物：
  描述：

  5-溴水杨醛 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (Z)-2-azido-3-(5-bromo-2-heptan-2-yloxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis and analgesic evaluation of 4-(2-heptyloxy)-7-[(Z)-(3-hydroxycyclohexyl)]indole: a caveat on indole-phenol bioisosterism

  摘要：

  The synthesis of 4-(2-heptyloxy)-7-[(Z)-(3-hydroxycyclohexyl)]indole (7) is described. Compound 7 was tested for analgesic properties in the phenylbenzoquinone writhing test and was found to be essentially devoid of activity. In contrast, cis-3-[4-(2-heptyloxy)-2-hydroxyphenyl]cyclohexanol (8), the analogue in which the pyrrolo ring is replaced by a hydroxyl group, had an ED50 of 8.3 mg/kg, sc, in the same model. The absence of bioisosterism between the pyrrolo ring and the phenolic hydroxyl group, in this instance, is discussed in terms of the circumstances that control the manifestation of bioisofunctionality between a pyrrolo ring and a phenolic hydroxyl group, which functions as a hydrogen-bond donor.

  DOI：

  10.1021/jm00158a023

文献信息

• SOLL R. M.; HUMBER L. G.; DEININGER D.; ASSELIN A. A.; CHAU THUY T.; WEIC+, J. MED. CHEM., 29,(1986) N 8, 1457-1460
  作者：SOLL R. M.、 HUMBER L. G.、 DEININGER D.、 ASSELIN A. A.、 CHAU THUY T.、 WEIC+

  DOI：——

  日期：——