4-Dimethylamino-4-(o-tolyl)-cyclohexanon | 65619-15-0

• 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-Dimethylamino-4-(o-tolyl)-cyclohexanon
• 英文别名: 4-(Dimethylamino)-4-(2-methylphenyl)cyclohexan-1-one
• CAS: 65619-15-0
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: BGOUSBRBUNITCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-dimethylamino-4-(o-tolyl)cyclohexanone, ethylene ketal hydroiodide 在 盐酸 作用下， 生成 4-Dimethylamino-4-(o-tolyl)-cyclohexanon
  参考文献：
  名称：

  DE2723937

  摘要：

  公开号：

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.
• US4065573A
  申请人：——

  公开号：US4065573A

  公开（公告）日：1977-12-27
• US4180584A
  申请人：——

  公开号：US4180584A

  公开（公告）日：1979-12-25
• US4460604A
  申请人：——

  公开号：US4460604A

  公开（公告）日：1984-07-17