5-methyl-1-(1-piperidinyl)cyclopentene | 86822-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-methyl-1-(1-piperidinyl)cyclopentene
• 英文别名: 1-(5-Methylcyclopenten-1-yl)piperidine；1-(5-methylcyclopenten-1-yl)piperidine
• CAS: 86822-55-1
• 化学式: C₁₁H₁₉N
• 分子量: 165.279
• InChiKey: MKODFYMMCOATTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methyl-1-(1-piperidinyl)cyclopentene 在 盐酸 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 26.0h， 生成 2-<(5-Methylspirodioxolan>-2-yl)methyl>benzonitril
  参考文献：
  名称：

  Schumann, Dieter; Naumann, Anneliese, Chemische Berichte, 1982, vol. 115, # 4, p. 1626 - 1635

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 2-甲基环戊酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以83%的产率得到5-methyl-1-(1-piperidinyl)cyclopentene
  参考文献：
  名称：

  Stereoselective reductions of substituted cyclohexyl and cyclopentyl carbon-nitrogen .pi. systems with hydride reagents

  摘要：

  DOI：

  10.1021/jo00168a009

文献信息

• Stereoselective reductions of substituted cyclohexyl and cyclopentyl carbon-nitrogen .pi. systems with hydride reagents
  作者：Robert O. Hutchins、Wei Yang Su、Ramachandran Sivakumar、Frank Cistone、Yuriy P. Stercho

  DOI：10.1021/jo00168a009

  日期：1983.10
• Schumann, Dieter; Naumann, Anneliese, Chemische Berichte, 1982, vol. 115, # 4, p. 1626 - 1635
  作者：Schumann, Dieter、Naumann, Anneliese

  DOI：——

  日期：——
• Synthesis, Biological Evaluation, and Structure−Activity Relationships of Dithiolethiones as Inducers of Cytoprotective Phase 2 Enzymes
  作者：Rex Munday、Yuesheng Zhang、Joseph D. Paonessa、Christine M. Munday、Alistair L. Wilkins、Jacob Babu

  DOI：10.1021/jm100425v

  日期：2010.6.24

  Dithiolethiones are a family of promising cancer chemopreventive agents, and induction of phase 2 enzymes is key to their chemopreventive activities. Two dithiolethiones have been evaluated in humans for cancer prevention. While some chemopreventive activities were detected in several human studies, potential side effects are a concern. Herein, we report structure-activity relationships of 25 dithiolethiones. Several compounds show exceedingly potent and bladder specific activity in phase 2 enzyme induction. Structural features responsible for such activity, as well as those inhibiting the activity, are discussed. Moreover, the compounds activate and depend on Nrf2 for their inductive activities. Nrf2 is a major transcriptional stimulator of cytoprotective genes and is critical for cancer prevention. Thus, several new dithiolethiones that are highly promising for bladder cancer prevention have been identified. Because the compounds act specifically in the bladder, the likelihood of potential systemic toxicity may be low.