2-methyl-5-(4-methoxybenzylidene)-cyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methyl-5-(4-methoxybenzylidene)-cyclopentanone
• 英文别名: (2E)-2-[(4-methoxyphenyl)methylidene]-5-methylcyclopentan-1-one
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: DKHHPDYNUFGHFZ-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  盐酸二甲胺 、 2-methyl-5-(4-methoxybenzylidene)-cyclopentanone 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以62%的产率得到(5E)-2-[(dimethylamino)methyl]-5-[(4-methoxyphenyl)methylidene]-2-methylcyclopentan-1-one;hydrochloride
  参考文献：
  名称：

  摘要：

  Purpose. A series of 2-substituted-2-dimethylaminomethyl-5-(E)-arylidene cyclopentanones, 4 were synthesized. The main objective of this investigation was to explore the structural parameters necessary for antiinflammatory activity in this series of compounds, while keeping cytotoxic action to a minimum.Methods. The target compounds were synthesized in two steps commencing with 2-alkyl-cyclopentanones. Antiinflammatory, analgesic and cytotoxic activities were determined in rats. Cytotoxic results were examined in human cell lines.Results. Eight of the eighteen synthetic substances possessed significant antiinflammatory activity and twelve showed appreciable analgesic action. Cytotoxicity was minimal or nonexistent for most of the compounds. The stability of one of the compounds, 4b in both aqueous and non-aqueous media, and an amine exchange reaction with aniline wee used to explain the observed antiinflammatory and cytotoxic activities.Conclusions. Unlike monosubstituted aminomethyl groups (Mannich bases) at the 2-position of 5-arylidene-2-cyclopentanones, a second substituent at the 2-position increases stability of the Mannich base and significantly decreases cytotoxic activity, Antiinflammatory and analgesic action is retained in many of the compounds, thus strongly indicating that these desired pharmacological results can be obtained without untoward damage to cells.

  DOI：

  10.1023/a:1016067210281
• 作为产物：
  描述：

  2-甲基环戊酮 、 4-甲氧基苯甲醛 以 水 为溶剂， 以85%的产率得到2-methyl-5-(4-methoxybenzylidene)-cyclopentanone
  参考文献：
  名称：

  Process for the preparation of arylidene-substituted alkylcycloalkanones

  摘要：

  芳香醛类化合物在碱性催化剂和水的存在下与烷基取代的环烷酮反应，制备了取代芳基亚醛烷基环戊酮。

  公开号：

  US05741937A1

文献信息

• Process for the preparation of arylidene-substituted alkylcycloalkanones
  申请人：Bayer Aktiengesellschaft

  公开号：US05741937A1

  公开（公告）日：1998-04-21

  Arylidene-substituted alkylcycloalkanones are prepared from alkyl-substituted cycloalkanones by reaction with aromatic carbonyl compounds in the presence of a basic catalyst and water.

  芳香醛类化合物在碱性催化剂和水的存在下与烷基取代的环烷酮反应，制备了取代芳基亚醛烷基环戊酮。
• Verfahren zur Herstellung von Arylidensubstituierten Alkylcycloalkanonen
  申请人：BAYER AG

  公开号：EP0751112A2

  公开（公告）日：1997-01-02

  Aryliden-substituierte Alkylcycloalkanone werden aus Alkyl-substituierten Cycloalkanonen durch Umsetzung mit aromatischen Carbonylverbindungen in Gegenwart eines basischen Katalysators und Wasser hergestellt.

  亚芳基取代的烷基环烷酮是由烷基取代的环烷酮在碱性催化剂和水的作用下与芳香族羰基化合物反应生成的。
• US5741937A
  申请人：——

  公开号：US5741937A

  公开（公告）日：1998-04-21
• ——
  作者：Haitao Chen、Zhizhong Ji、Lan K. Wong、Jerome F. Siuda、Ven L. Narayanan

  DOI：10.1023/a:1016067210281

  日期：——

  Purpose. A series of 2-substituted-2-dimethylaminomethyl-5-(E)-arylidene cyclopentanones, 4 were synthesized. The main objective of this investigation was to explore the structural parameters necessary for antiinflammatory activity in this series of compounds, while keeping cytotoxic action to a minimum.Methods. The target compounds were synthesized in two steps commencing with 2-alkyl-cyclopentanones. Antiinflammatory, analgesic and cytotoxic activities were determined in rats. Cytotoxic results were examined in human cell lines.Results. Eight of the eighteen synthetic substances possessed significant antiinflammatory activity and twelve showed appreciable analgesic action. Cytotoxicity was minimal or nonexistent for most of the compounds. The stability of one of the compounds, 4b in both aqueous and non-aqueous media, and an amine exchange reaction with aniline wee used to explain the observed antiinflammatory and cytotoxic activities.Conclusions. Unlike monosubstituted aminomethyl groups (Mannich bases) at the 2-position of 5-arylidene-2-cyclopentanones, a second substituent at the 2-position increases stability of the Mannich base and significantly decreases cytotoxic activity, Antiinflammatory and analgesic action is retained in many of the compounds, thus strongly indicating that these desired pharmacological results can be obtained without untoward damage to cells.