8-(4-溴-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-羧酸 | 65619-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 8-(4-溴-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-羧酸
• 英文名称: 8-(4-Bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylic acid
• CAS: 65619-36-5
• 化学式: C₁₅H₁₇BrO₄
• 分子量: 341.202
• InChiKey: DEPICSDGZVSRTH-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(4-溴-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-羧酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以49%的产率得到8-(4-Bromophenyl)-8-isocyanato-1,4-dioxaspiro[4.5]decane
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014
• 作为产物：
  描述：

  4-(p-Bromphenyl)-2-carbomethoxy-4-cyano-cyclohexanon 在 sodium hydroxide 、 硫酸 、 对甲苯磺酸 作用下， 以 乙二醇 、 溶剂黄146 、 苯 为溶剂， 反应 48.0h， 生成 8-(4-溴-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-羧酸
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014

文献信息

• LEDNICER D.; VOIGTLANDER P. F.; EMMERT D. E., J. MED. CHEM., 1980, 23, NO 4, 424-430
  作者：LEDNICER D.、 VOIGTLANDER P. F.、 EMMERT D. E.

  DOI：——

  日期：——