(Z)-6-[2-[(Z)-5-cyanopent-4-enyl]-1,3-dioxolan-2-yl]hex-2-enenitrile | 1245608-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-6-[2-[(Z)-5-cyanopent-4-enyl]-1,3-dioxolan-2-yl]hex-2-enenitrile
• CAS: 1245608-73-4
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: JJUHEEXCBMBTHR-VHOZIDCHSA-N

物化性质

• 沸点：
  422.6±20.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-6-[2-[(Z)-5-cyanopent-4-enyl]-1,3-dioxolan-2-yl]hex-2-enenitrile 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以95%的产率得到(Z,Z)-tridecan-2,11-diene-7-one-1,13-dinitrile
  参考文献：
  名称：

  Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids

  摘要：

  A domino cyclization reaction of the bis-unsaturated ketone 3 with hydroxylamine proceeds with good yield and high stereoselectivity, in a flow reactor system. The tricyclic spiropiperidine products 5 and 2 obtained are valuable building blocks for the synthesis of analogues of the histrionicotoxin alkaloids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.092
• 作为产物：
  描述：

  1,3-Dioxolane-2,2-dibutanal 、 (1,1-dimethylethoxy)diphenylsilylacetonitrile 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到(Z)-6-[2-[(Z)-5-cyanopent-4-enyl]-1,3-dioxolan-2-yl]hex-2-enenitrile
  参考文献：
  名称：

  Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids

  摘要：

  A domino cyclization reaction of the bis-unsaturated ketone 3 with hydroxylamine proceeds with good yield and high stereoselectivity, in a flow reactor system. The tricyclic spiropiperidine products 5 and 2 obtained are valuable building blocks for the synthesis of analogues of the histrionicotoxin alkaloids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.092

文献信息

• Flow synthesis of tricyclic spiropiperidines as building blocks for the histrionicotoxin family of alkaloids
  作者：Malte Brasholz、Brian A. Johnson、James M. Macdonald、Anastasios Polyzos、John Tsanaktsidis、Simon Saubern、Andrew B. Holmes、John H. Ryan

  DOI：10.1016/j.tet.2010.04.092

  日期：2010.8

  A domino cyclization reaction of the bis-unsaturated ketone 3 with hydroxylamine proceeds with good yield and high stereoselectivity, in a flow reactor system. The tricyclic spiropiperidine products 5 and 2 obtained are valuable building blocks for the synthesis of analogues of the histrionicotoxin alkaloids. (C) 2010 Elsevier Ltd. All rights reserved.