7-phenyl-7-azabicyclo[4.1.0]hept-3-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-phenyl-7-azabicyclo[4.1.0]hept-3-ene
• 英文别名: (1S,6R)-7-phenyl-7-azabicyclo[4.1.0]hept-3-ene
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: AQQFXQLKQRJHBF-FUNVUKJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-phenyl-7-azabicyclo[4.1.0]hept-3-ene 、 异戊硫醇 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以91%的产率得到
  参考文献：
  名称：

  Indium(III) chloride-catalyzed thiolysis of meso-aziridines

  摘要：

  Indium(III) chloride efficiently catalyzed the thiol addition to meso-aziridines at very low substrate-catalyst ratios giving rise to 1,2-amino sulfides in excellent yields and complete diastereocontrol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.082

文献信息

• The Ti-BINOLate-catalyzed, enantioselective ring-opening of meso-aziridines with amines
  作者：Saravanan Peruncheralathan、Sandra Aurich、Henrik Teller、Christoph Schneider

  DOI：10.1039/c3ob40222c

  日期：——

  The titanium-BINOLate-catalyzed, highly enantioselective ring-opening reaction of meso-aziridines has been developed which furnishes trans-1,2-diamines in typically good yields and excellent enantioselectivities. N-Aryl aziridines attached to a 5- or 6-membered carbocyclic ring are among the best substrates for this process providing the products in up to >99% ee. The chiral catalyst is easily prepared in situ from commercially available components and does not require any laborious ligand synthesis. Structural investigations into the catalyst composition reveal an oligomeric structure of the active Ti-complex.

  开发了由钛-BINOLate催化的高对映选择性meso-氮杂环的开环反应，该反应通常能以良好的产率和优异的对映选择性生成trans-1,2-二胺。N-芳基氮杂环与5-或6-成员碳环相连，是此过程的最佳底物之一，产物的对映体过量可达>99%。该手性催化剂可通过市售组分原位简便制备，无需繁琐的配体合成。对催化剂组成的结构研究显示，其活性钛复合物具有低聚合结构。
• Cationic Late-Transition-Metal Complexes Catalyze the Ring Opening of Aziridines with Amines
  作者：Christoph Schneider、Alex Marti、Saravanan Peruncheralathan

  DOI：10.1055/s-0031-1289611

  日期：2012.1

  Cationic palladium and nickel complexes have been found to catalyze the ring-opening of meso-N-aryl aziridines with anilines very efficiently and furnish valuable 1,2-diamines in typically excellent yields. The active catalysts were generated in situ from the corresponding metal dichloride bis(triphenylphosphine) complexes through chloride abstraction with a silver salt. This new protocol is applicable across a broad substrate range with both cyclic as well as acyclic aziridines. In addition, cationic gold-phosphine complexes proved to be highly reactive as well as delivering products in comparable rates and yields.

  阳离子钯和镍配合物已被发现能够非常有效地催化间-N-芳基氮丙啶与苯胺的环开环反应，并生成有价值的1,2-二胺，且产率通常很高。活性催化剂是通过用银盐进行氯化物提取，从相应的金属二氯化物双（三苯基膦）配合物中原位生成的。这种新方法适用于广泛的底物范围，包括环状和非环状氮丙啶。此外，阳离子金-膦配合物被证明具有高反应性，且产率和产率相当。
• Indium(III) chloride-catalyzed thiolysis of meso-aziridines
  作者：Saravanan Peruncheralathan、Michael Henze、Christoph Schneider

  DOI：10.1016/j.tetlet.2007.07.082

  日期：2007.9

  Indium(III) chloride efficiently catalyzed the thiol addition to meso-aziridines at very low substrate-catalyst ratios giving rise to 1,2-amino sulfides in excellent yields and complete diastereocontrol. (c) 2007 Elsevier Ltd. All rights reserved.