(Z)-N,N’-diphenyloct-4-ene-1,8-diamine | 1415263-79-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-N,N’-diphenyloct-4-ene-1,8-diamine
• CAS: 1415263-79-4
• 化学式: C₂₀H₂₆N₂
• 分子量: 294.44
• InChiKey: HGRPIAPKLLLJJY-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-N,N’-diphenyloct-4-ene-1,8-diamine 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以67%的产率得到trans-N,N'-diphenyl-2,2'-bipyrrolidine
  参考文献：
  名称：

  Efficient Synthesis of Chiral 2,2′-Bipyrrolidines by an anti-Selective Alkene Diamination

  摘要：

  The rapid and efficient construction of complex chiral bicyclic amines is possible using a novel alkene diamination reaction. Electrophilic iodinating agents promote the intramolecular anti-selective diamination of alkenes and allow the efficient synthesis of chiral amines such as trans-bipyrrolidines.

  DOI：

  10.1021/ol302855z
• 作为产物：
  描述：

  (Z)-oct-4-enedial 、 苯胺 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以49%的产率得到(Z)-N,N’-diphenyloct-4-ene-1,8-diamine
  参考文献：
  名称：

  Efficient Synthesis of Chiral 2,2′-Bipyrrolidines by an anti-Selective Alkene Diamination

  摘要：

  The rapid and efficient construction of complex chiral bicyclic amines is possible using a novel alkene diamination reaction. Electrophilic iodinating agents promote the intramolecular anti-selective diamination of alkenes and allow the efficient synthesis of chiral amines such as trans-bipyrrolidines.

  DOI：

  10.1021/ol302855z

文献信息

• <i>Z</i>-Selective Ethenolysis with a Ruthenium Metathesis Catalyst: Experiment and Theory
  作者：Hiroshi Miyazaki、Myles B. Herbert、Peng Liu、Xiaofei Dong、Xiufang Xu、Benjamin K. Keitz、Thay Ung、Garik Mkrtumyan、K. N. Houk、Robert H. Grubbs

  DOI：10.1021/ja4010267

  日期：2013.4.17

  The Z-selective ethenolysis activity of chelated ruthenium metathesis catalysts was investigated with experiment and theory. A five-membered chelated catalyst that was successfully employed in Z-selective cross metathesis reactions has now been found to be highly active for Z-selective ethenolysis at low ethylene pressures, while tolerating a wide variety of functional groups. This phenomenon also affects its activity in cross metathesis reactions and prohibits crossover reactions of internal olefins via trisubstituted ruthenacyclobutane intermediates. In contrast, a related catalyst containing a six-membered chelated architecture is not active for ethenolysis and seems to react through different pathways more reminiscent of previous generations of ruthenium catalysts. Computational investigations of the effects of substitution on relevant transition states and ruthenacyclobutane intermediates revealed that the differences of activities are attributed to the steric repulsions of the anionic ligand with the chelating groups.