2-(2-庚氧基)-5-溴苯甲醛 | 102651-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2-庚氧基)-5-溴苯甲醛
• 英文名称: 2-(2-heptyloxy)-5-bromobenzaldehyde
• 英文别名: 5-Bromo-2-heptan-2-yloxybenzaldehyde
• CAS: 102651-61-6
• 化学式: C₁₄H₁₉BrO₂
• 分子量: 299.208
• InChiKey: FXASIXYWHNCKGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-庚氧基)-5-溴苯甲醛 在 sodium hydroxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 copper chromite 、 三丁基膦 、 三氟化硼乙醚 、 叔丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 喹啉 、 甲醇 、 xylene 为溶剂， 反应 1.17h， 生成 N-(triisopropylsilyl)-4-(2-heptyloxy)-7-indole
  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：

  2-溴庚烷 、 5-溴水杨醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到2-(2-庚氧基)-5-溴苯甲醛
  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：——