4-(p-bromophenyl)-4-dimethylaminocyclohexan-1-one. ethylene ketal | 71368-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(p-bromophenyl)-4-dimethylaminocyclohexan-1-one. ethylene ketal
• 英文别名: 8-(4-bromophenyl)-N,N-dimethyl-1,4-dioxaspiro[4.5]decan-8-amine
• CAS: 71368-46-2
• 化学式: C₁₆H₂₂BrNO₂
• 分子量: 340.26
• InChiKey: BAAHUWRTCFXPNN-UHFFFAOYSA-N

物化性质

• 沸点：
  408.8±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-(4-溴-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-甲腈 在 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 36.0h， 生成 4-(p-bromophenyl)-4-dimethylaminocyclohexan-1-one. ethylene ketal
  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

• 4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring
  作者：Daniel Lednicer、Philip F. Von Voigtlander、D. Edward Emmert

  DOI：10.1021/jm00178a014

  日期：1980.4

  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.