Z-2,3-diazido-3-phenyl-propenal | 866315-34-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: Z-2,3-diazido-3-phenyl-propenal
• 英文别名: (Z)-2,3-diazidocinnamaldehyde；(Z)-2,3-diazido-3-phenylprop-2-enal
• CAS: 866315-34-6
• 化学式: C₉H₆N₆O
• 分子量: 214.186
• InChiKey: IPWOBMLHILZCQK-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-2,3-diazido-3-phenyl-propenal 反应 0.19h， 生成 glyoxylonitrile
  参考文献：
  名称：

  开链1,2-二叠氮烯的光解：生成2-叠氮基-2 H-叠氮基，甲酰氰和甲酰异氰

  摘要：

  几种开链1,2-二叠氮基乙烯的溶液进行光解，生成2-叠氮基-2 H-叠氮基，可在低温下通过NMR光谱法鉴定。在NMR溶液长时间辐照或预热后，这些杂环会损失第二个氮分子，从而被裂解为氰基化合物的两个片段。在（Z）-2，3-重氮二甲醛中，当在氩气基质中进行光解时，通过IR光谱法检测到甲酰氰的形成。后者的物质在辐照下重排为甲酰基异氰化物。通过比较实验和计算得出的（B3LYP / 6-311 + G ∗）红外光谱，对这种新物种进行了表征。

  DOI：

  10.1016/j.tet.2008.04.037
• 作为产物：
  描述：

  Z-2-azido-3-chloro-3-phenyl-propenal 在 hexadecyltributylphosphonium azide 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以86%的产率得到Z-2,3-diazido-3-phenyl-propenal
  参考文献：
  名称：

  First successful synthesis, isolation and characterization of open-chain 1,2-diazidoethenes

  摘要：

  Open-chain 1,2-diazidoethenes have been obtained from the recently reported acceptor-substituted propargyl azides by one-pot reactions with tetramethylguanidinium azide (TMGA) and in some cases via a two-step procedure starting with in situ production of the corresponding azidoallene followed by addition of hydrazoic acid with the help of TMGA. In a different synthetic pathway, the substitution reactions between 2-azido-3-haloacroleins and hexadecyltributylphosphonium azide (QN(3)) have been used. In order to have more evidence for their structures, some diazido compounds were converted to their bis-triazole derivatives through 1,3-dipolar cycloaddition. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.025

文献信息

• Photolysis of open-chain 1,2-diazidoalkenes: generation of 2-azido-2H-azirines, formyl cyanide, and formyl isocyanide
  作者：Klaus Banert、Joseph Rodolph Fotsing、Manfred Hagedorn、Hans Peter Reisenauer、Günther Maier

  DOI：10.1016/j.tet.2008.04.037

  日期：2008.6

  nitrogen to be cleaved into two fragments of cyano compounds. In the case of (Z)-2,3-diazidocinnamaldehyde, the formation of formyl cyanide was detected by IR spectroscopy when the photolysis was performed in argon matrix. The latter substance was rearranged to formyl isocyanide on irradiation. This new species was characterized by comparison of its experimental and calculated (B3LYP/6-311+G∗∗) IR spectrum

  几种开链1,2-二叠氮基乙烯的溶液进行光解，生成2-叠氮基-2 H-叠氮基，可在低温下通过NMR光谱法鉴定。在NMR溶液长时间辐照或预热后，这些杂环会损失第二个氮分子，从而被裂解为氰基化合物的两个片段。在（Z）-2，3-重氮二甲醛中，当在氩气基质中进行光解时，通过IR光谱法检测到甲酰氰的形成。后者的物质在辐照下重排为甲酰基异氰化物。通过比较实验和计算得出的（B3LYP / 6-311 + G ∗）红外光谱，对这种新物种进行了表征。
• First successful synthesis, isolation and characterization of open-chain 1,2-diazidoethenes
  作者：Joseph Rodolph Fotsing、Manfred Hagedorn、Klaus Banert

  DOI：10.1016/j.tet.2005.07.025

  日期：2005.9

  Open-chain 1,2-diazidoethenes have been obtained from the recently reported acceptor-substituted propargyl azides by one-pot reactions with tetramethylguanidinium azide (TMGA) and in some cases via a two-step procedure starting with in situ production of the corresponding azidoallene followed by addition of hydrazoic acid with the help of TMGA. In a different synthetic pathway, the substitution reactions between 2-azido-3-haloacroleins and hexadecyltributylphosphonium azide (QN(3)) have been used. In order to have more evidence for their structures, some diazido compounds were converted to their bis-triazole derivatives through 1,3-dipolar cycloaddition. (c) 2005 Elsevier Ltd. All rights reserved.