N-cinnamylcyanamide | 109058-91-5

• 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: N-cinnamylcyanamide
• 英文别名: 3-phenylprop-2-enylcyanamide
• CAS: 109058-91-5
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: UDJPVHZXWXPJNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.82
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-cinnamylcyanamide 在 盐酸 、 偶氮二异丁腈 、 2-甲基十一烷-2-硫醇 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙腈 、 mineral oil 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Synthesis of Diverse Boron-Handled N-Heterocycles via Radical Borylative Cyclization of N-Allylcyanamides

  摘要：

  A synthetic method based on radical borylation/cyclization cascades of N-allylcyanamides was developed to construct diverse boron-substituted N-heterocycles. In the reaction process, the N-heterocyclic carbene-boryl radical underwent a chemo- and regioselective addition to the alkene moiety, followed by cyclization with the N-cyano group. The resulting amide-iminyl radical intermediates underwent further reactions to afford various boron-tethered N-heterocyclic molecules. Further transformations to access synthetically useful building blocks were also demonstrated.

  DOI：

  10.1021/acs.orglett.8b03303
• 作为产物：
  描述：

  N-(1-phenyl-2-propenyl)cyanamide 以 xylene 为溶剂， 反应 110.0h， 以95%的产率得到N-cinnamylcyanamide
  参考文献：
  名称：

  烯丙基氰胺的热重排

  摘要：

  氰酰胺的烯丙基重排是通过在125至190°C的温度下在溶液中热解而实现的。在氰基氮丙啶中氮丙啶环的热打开期间也观察到这种重排。该烯丙基转座构成用于烯丙基胺的1，3-异构化的正式方法。

  DOI：

  10.1016/s0040-4039(00)85064-9

文献信息

• Electrochemical Trifluoromethylation/Bicyclization of <i>N</i>-Cyanamide Alkenes: Synthesis of Bicyclic Amidine Derivatives
  作者：Zhi-Hua Yan、Yan Yan、Zhong-Lin Wei、Wei-Wei Liao

  DOI：10.1021/acs.joc.3c02777

  日期：2024.2.16

  available starting materials furnished nonaromatic fused azaheterobicyclic compounds in a highly efficient and sustainable manner. The broad substrate scope, facile scalability, and sustainability enabled this electrochemical process to be an appealing complement for trifluoromethylated cyclic amidines.

  报道了带有两个电子差异的烯烃部分的N-氰酰胺烯烃的阳极氧化三氟甲基化级联，其中各种N-不饱和酰基氰酰胺烯烃和CF 3 SO 2 Na作为容易获得的起始材料，以高效且可靠的方式提供非芳香族稠合氮杂双环化合物。可持续的方式。广泛的底物范围、易于扩展和可持续性使该电化学过程成为三氟甲基化环脒的有吸引力的补充。
• Synthesis of Diverse Boron-Handled N-Heterocycles via Radical Borylative Cyclization of <i>N</i>-Allylcyanamides
  作者：Ji-Kang Jin、Feng-Lian Zhang、Qiang Zhao、Jun-An Lu、Yi-Feng Wang

  DOI：10.1021/acs.orglett.8b03303

  日期：2018.12.7

  A synthetic method based on radical borylation/cyclization cascades of N-allylcyanamides was developed to construct diverse boron-substituted N-heterocycles. In the reaction process, the N-heterocyclic carbene-boryl radical underwent a chemo- and regioselective addition to the alkene moiety, followed by cyclization with the N-cyano group. The resulting amide-iminyl radical intermediates underwent further reactions to afford various boron-tethered N-heterocyclic molecules. Further transformations to access synthetically useful building blocks were also demonstrated.
• Thermal rearrangement of allylic cyanamides
  作者：Carmen Betancor、Reyes Carrau、Cosme G Francisco、Ernesto Suárez

  DOI：10.1016/s0040-4039(00)85064-9

  日期：1986.1

  The allylic rearrangement of cyanamides has been achieved by pyrolysis in solution at temperatures between 125 and 190 °C. This rearrangement was also observed during the thermal opening of the aziridine ring in cyanoaziridines. This allylic transposition constitutes a formal method for the 1,3-isomerization of allylic amines.

  氰酰胺的烯丙基重排是通过在125至190°C的温度下在溶液中热解而实现的。在氰基氮丙啶中氮丙啶环的热打开期间也观察到这种重排。该烯丙基转座构成用于烯丙基胺的1，3-异构化的正式方法。