N-(hex-5-en-2-ylidene)semicarbazide | 339207-38-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: N-(hex-5-en-2-ylidene)semicarbazide
• CAS: 339207-38-4
• 化学式: C₇H₁₃N₃O
• 分子量: 155.2
• InChiKey: BKHYMKCMJNYQRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.48
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(hex-5-en-2-ylidene)semicarbazide 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以49%的产率得到N-(hex-5-en-2-yl)semicarbazide
  参考文献：
  名称：

  Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation

  摘要：

  Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230 degrees C), afford intramolecular hydroamination products upon heating at high temperatures (120-235 degrees C). A concerted Cope-type hydroamination event, followed by a hydrazide-mediated proton transfer step of the hydrazinium ylide intermediate, is proposed and supported by DFT calculations. In contrast, a simple modification of the reagent structure (R = Ot-Bu or NH2) favors the formation of aminocarbonylation products at 200 degrees C, and the tatter reaction is shown to be stereospecific.

  DOI：

  10.1021/ja902558j
• 作为产物：
  描述：

  5-已烯-2-酮 、 S-(4-叔-丁基苯甲基)[2-(1-甲基丁基)吡啶-3-基]硫代氨基甲酸酯 在 盐酸 作用下， 以 甲醇 为溶剂， 以100%的产率得到N-(hex-5-en-2-ylidene)semicarbazide
  参考文献：
  名称：

  Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation

  摘要：

  Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230 degrees C), afford intramolecular hydroamination products upon heating at high temperatures (120-235 degrees C). A concerted Cope-type hydroamination event, followed by a hydrazide-mediated proton transfer step of the hydrazinium ylide intermediate, is proposed and supported by DFT calculations. In contrast, a simple modification of the reagent structure (R = Ot-Bu or NH2) favors the formation of aminocarbonylation products at 200 degrees C, and the tatter reaction is shown to be stereospecific.

  DOI：

  10.1021/ja902558j

文献信息

• Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation
  作者：Jean-Grégoire Roveda、Christian Clavette、Ashley D. Hunt、Serge I. Gorelsky、Christopher J. Whipp、André M. Beauchemin

  DOI：10.1021/ja902558j

  日期：2009.7.1

  Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230 degrees C), afford intramolecular hydroamination products upon heating at high temperatures (120-235 degrees C). A concerted Cope-type hydroamination event, followed by a hydrazide-mediated proton transfer step of the hydrazinium ylide intermediate, is proposed and supported by DFT calculations. In contrast, a simple modification of the reagent structure (R = Ot-Bu or NH2) favors the formation of aminocarbonylation products at 200 degrees C, and the tatter reaction is shown to be stereospecific.