(3E,5Z)-4-((benzylamino)(phenyl)methyl)hepta-3,5-dien-1-ol | 1193433-97-4

• 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: (3E,5Z)-4-((benzylamino)(phenyl)methyl)hepta-3,5-dien-1-ol
• 英文别名: (3E,5Z)-4-[(benzylamino)-phenylmethyl]hepta-3,5-dien-1-ol
• CAS: 1193433-97-4
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: BEYOJTXSPXBJKU-GJSBCOJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三聚甲醛 、 (3E,5Z)-4-((benzylamino)(phenyl)methyl)hepta-3,5-dien-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， 生成 (5R,8S,8aR)-6-benzyl-8-methyl-5-phenyl-3,5,6,7,8,8a-hexahydro-2H-pyrano[3,2-c]pyridine 、 (5R,8S,8aS)-6-benzyl-8-methyl-5-phenyl-3,5,6,7,8,8a-hexahydro-2H-pyrano[3,2-c]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：

  、 N-苄烯丁胺 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74%的产率得到(3E,5Z)-4-((benzylamino)(phenyl)methyl)hepta-3,5-dien-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