Methyl 5-cyano-5-(m-methoxyphenyl)-2-oxocyclohexanecarboxylate | 13225-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 5-cyano-5-(m-methoxyphenyl)-2-oxocyclohexanecarboxylate
• 英文别名: methyl 5-cyano-5-(3-methoxyphenyl)-2-oxocyclohexane-1-carboxylate
• CAS: 13225-33-7
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: LONXWYJMUFQXME-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  469.1±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 5-cyano-5-(m-methoxyphenyl)-2-oxocyclohexanecarboxylate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 、 叠氮磷酸二苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇 、 溶剂黄146 、 苯 为溶剂， 反应 54.0h， 生成 8-(3-methoxyphenyl)-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine
  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：

  γ-Cyan-γ-(3-methoxy-phenyl)-pimelinsaeure-methylester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以99%的产率得到Methyl 5-cyano-5-(m-methoxyphenyl)-2-oxocyclohexanecarboxylate
  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：——
• US4065573A
  申请人：——

  公开号：US4065573A

  公开（公告）日：1977-12-27
• US4113866A
  申请人：——

  公开号：US4113866A

  公开（公告）日：1978-09-12
• US4180584A
  申请人：——

  公开号：US4180584A

  公开（公告）日：1979-12-25
• US4447454A
  申请人：——

  公开号：US4447454A

  公开（公告）日：1984-05-08

表征谱图