(E)-5-(3-chlorophenyl)-4-(1-cyclopentenyl)-5-(propylamino)pent-3-en-1-ol | 1193433-99-6

• 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: (E)-5-(3-chlorophenyl)-4-(1-cyclopentenyl)-5-(propylamino)pent-3-en-1-ol
• CAS: 1193433-99-6
• 化学式: C₁₉H₂₆ClNO
• 分子量: 319.875
• InChiKey: FDDZZXHJRZSZTP-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三聚甲醛 、 (E)-5-(3-chlorophenyl)-4-(1-cyclopentenyl)-5-(propylamino)pent-3-en-1-ol 在 D(+)-10-樟脑磺酸 、 sodium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 20.0h， 以57%的产率得到(5S,7aR,10(1)S)-5-(3-chlorophenyl)-6-propyl-3,5,6,7,7a,8,9,10-octahydro-2H-cyclopenta[c]pyrano[2,3-d]pyridine
  参考文献：
  名称：

  Convergent Synthesis of Piperidines by the Union of Conjugated Alkynes with Imines: A Unique Regioselective Bond Construction for Heterocycle Synthesis

  摘要：

  A two-step process is described for the union of aromatic imines, conjugated alkynes, and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings.

  DOI：

  10.1021/ol902169k
• 作为产物：
  描述：

  、 [1-(3-Chloro-phenyl)-meth-(E)-ylidene]-propyl-amine 在 titanium(IV) isopropylate 、 Cyclopentylmagnesium chloride 、 水 、 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 9.0h， 以67%的产率得到(E)-5-(3-chlorophenyl)-4-(1-cyclopentenyl)-5-(propylamino)pent-3-en-1-ol
  参考文献：
  名称：

  Convergent Synthesis of Piperidines by the Union of Conjugated Alkynes with Imines: A Unique Regioselective Bond Construction for Heterocycle Synthesis

  摘要：

  A two-step process is described for the union of aromatic imines, conjugated alkynes, and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings.

  DOI：

  10.1021/ol902169k