N-phenyl-4-vinylbenzaldimine | 67735-81-3

• 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-phenyl-4-vinylbenzaldimine
• 英文别名: 1-(4-ethenylphenyl)-N-phenylmethanimine
• CAS: 67735-81-3
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: OOXSYQKTPQPCTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-phenyl-4-vinylbenzaldimine 、 苯硅烷 在 2,6-bis[1-(2,6-diethylphenylimino)ethyl]pyridine iron(II) triflate 、 N,N-二异丙基乙胺 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 以39%的产率得到phenyl(N-[(4-ethylphenyl)methylene]benzenamine)silane
  参考文献：
  名称：

  胺活化的铁催化：空气和水分稳定的烯烃和炔烃加氢官能化

  摘要：

  一种简单的烷基胺[（i Pr）2 NEt]已用于活化对空气和水分稳定的铁（II）预催化剂，用于烯烃和炔烃的加氢官能​​化反应。这种胺活化仅使用0.25–2 mol％的铁催化剂和1–25 mol％的胺即可实现烯烃和炔烃的高度操作简单的氢化硅烷化和氢硼化。明显地，这些反应在空气和惰性反应条件下均以相等的产率进行。

  DOI：

  10.1002/adsc.201600570
• 作为产物：
  描述：

  对苯二甲醛 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 N-phenyl-4-vinylbenzaldimine
  参考文献：
  名称：

  使用台式稳定的铁（II）预催化剂进行铁催化的烯烃和炔烃的化学，区域和立体选择性氢化硅烷化

  摘要：

  AbstractThe chemo‐, regio‐, and stereoselective iron‐catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41–96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron‐catalysed hydrosilylation. The silane products can be oxidised to the anti‐Markovnikov product of olefin hydration, and the one‐pot iron‐catalysed hydrosilylation–oxidation of olefins to give silane(di)ols directly is also reported. The iron pre‐catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 mol h−1. Initial mechanistic studies indicate an iron(I) active catalyst.magnified image

  DOI：

  10.1002/adsc.201300827

文献信息

• Iron-Catalysed Chemo-, Regio-, and Stereoselective Hydrosilylation of Alkenes and Alkynes using a Bench-Stable Iron(II) Pre-Catalyst
  作者：Mark D. Greenhalgh、Dominik J. Frank、Stephen P. Thomas

  DOI：10.1002/adsc.201300827

  日期：2014.2.10

  AbstractThe chemo‐, regio‐, and stereoselective iron‐catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41–96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron‐catalysed hydrosilylation. The silane products can be oxidised to the anti‐Markovnikov product of olefin hydration, and the one‐pot iron‐catalysed hydrosilylation–oxidation of olefins to give silane(di)ols directly is also reported. The iron pre‐catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 mol h−1. Initial mechanistic studies indicate an iron(I) active catalyst.magnified image
• Amine-Activated Iron Catalysis: Air- and Moisture-Stable Alkene and Alkyne Hydrofunctionalization
  作者：Amy J. Challinor、Marc Calin、Gary S. Nichol、Neil B. Carter、Stephen P. Thomas

  DOI：10.1002/adsc.201600570

  日期：2016.7.28

  an air‐ and moisture‐stable iron(II) pre‐catalyst for alkene and alkyne hydrofunctionalization reactions. This amine activation has enabled the highly operationally simple hydrosilylation and hydroboration of alkenes and alkynes using just 0.25–2 mol% iron catalyst and 1–25 mol% amine. Significantly, these reactions proceed in equal yield under both air and inert reaction conditions.

  一种简单的烷基胺[（i Pr）2 NEt]已用于活化对空气和水分稳定的铁（II）预催化剂，用于烯烃和炔烃的加氢官能​​化反应。这种胺活化仅使用0.25–2 mol％的铁催化剂和1–25 mol％的胺即可实现烯烃和炔烃的高度操作简单的氢化硅烷化和氢硼化。明显地，这些反应在空气和惰性反应条件下均以相等的产率进行。