(E)-4-(cyclopenten-1-yl)-5-(4,4-dimethoxybutylamino)-5-phenylpent-3-en-1-ol | 1193433-76-9

• 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)-4-(cyclopenten-1-yl)-5-(4,4-dimethoxybutylamino)-5-phenylpent-3-en-1-ol
• CAS: 1193433-76-9
• 化学式: C₂₂H₃₃NO₃
• 分子量: 359.509
• InChiKey: ZPSVNYHDUBDMJP-XSFVSMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(cyclopenten-1-yl)-5-(4,4-dimethoxybutylamino)-5-phenylpent-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52%的产率得到(3(1)S,8R,12aR,12bR)-8-phenyl-2,3,5,6,8,10,11,12,12a,12b-decahydro-1H-cyclopenta[g]pyrano[3,2-f]indolizine
  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：

  N-benzylidene-4,4-dimethoxybutan-1-amine 、 在 titanium(IV) isopropylate 、 Cyclopentylmagnesium chloride 、 水 、 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 17.0h， 以52%的产率得到(E)-4-(cyclopenten-1-yl)-5-(4,4-dimethoxybutylamino)-5-phenylpent-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