(E)-4-(benzo[d][1,3]dioxol-5-yl)-5-(benzylamino)-5-phenylpent-3-en-1-ol | 1193433-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-4-(benzo[d][1,3]dioxol-5-yl)-5-(benzylamino)-5-phenylpent-3-en-1-ol
• CAS: 1193433-96-3
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: JBCNVWIPTXKEMX-WSDLNYQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  三聚甲醛 、 (E)-4-(benzo[d][1,3]dioxol-5-yl)-5-(benzylamino)-5-phenylpent-3-en-1-ol 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 氯仿 为溶剂， 反应 20.0h， 以79%的产率得到(E)-3-(6-benzyl-7-phenyl-6,7-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-8(5H)-ylidene)propan-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
• 作为产物：
  描述：

  、 N-苄烯丁胺 在 titanium(IV) isopropylate 、 Cyclopentylmagnesium chloride 、 水 、 碳酸氢钠 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 8.5h， 以42%的产率得到(E)-4-(benzo[d][1,3]dioxol-5-yl)-5-(benzylamino)-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