trans-diphenyl-1-propenylamine | 133496-88-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-diphenyl-1-propenylamine
• 英文别名: N-phenyl-N-[(E)-prop-1-enyl]aniline
• CAS: 133496-88-5
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: UTHJIQQHQKJNTF-XNJYKOPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-烯丙基-N-苯基苯胺 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 trans-diphenyl-1-propenylamine
  参考文献：
  名称：

  Functionalized organolithium reagents. 9. Lithiation and isomerization of allylic amines as a general route to enamines and their carbonyl derivatives

  摘要：

  [3-(Diphenylamino)-2-propenyl]lithium, readily prepared by the lithiation of allyldiphenylamine with n-butyllithium in THF, undergoes alkylation either with organic halides or with carbonyl or azomethine derivatives to yield enamines, which can be converted by protons or other electrophiles into aldehydes or into five-membered heterocycles; lithiation of such allyldiarylamines with other reagents leads principally to isomerization to enamines (with lithium diisopropylamide) or to carbenoid intermediates (tert-butyllithium and potassium tert-butoxide).

  DOI：

  10.1021/jo00009a005

文献信息

• Catalytic 1,3-Proton Transfer in Alkenes Enabled by Fe═NR Bond Cooperativity: A Strategy for p<i>K</i>_a-Dictated Regioselective Transposition of C═C Double Bonds
  作者：Yafei Gao、Xuelian Li、Jeremiah E. Stevens、Hao Tang、Jeremy M. Smith

  DOI：10.1021/jacs.2c13350

  日期：2023.6.7

  (1-K(18-C-6)) catalyzes 1,3-proton transfer from 1-alkene substrates to afford 2-alkene transposition products. Mechanistic investigations involving kinetics, competition, and isotope labeling studies, supported by experimentally calibrated DFT computations, strongly support an unusual nonhydridic mechanism for alkene transposition that is enabled by the cooperative action of the iron center and basic imido ligand

  过渡金属催化的烯烃双键转位通常涉及金属氢化物中间体。尽管在决定产品选择性的催化剂设计方面取得了重大进展，但对底物选择性的控制却不太先进，而且在含有多个 1-烯烃官能团的底物中选择性转位双键的过渡金属催化剂很少见。在此，我们报道了三坐标高自旋 ( S = 2) Fe(II) 亚胺络合物 [Ph 2 B( t BuIm) 2 Fe═NDipp][K(18-C-6)THF 2 ] ( 1- K(18-C-6)) 催化 1,3-质子从 1-烯烃底物转移，得到 2-烯烃转座产物。由实验校准的 DFT 计算支持的涉及动力学、竞争和同位素标记研究的机理研究强烈支持一种不寻常的烯烃转座非氢化机制，这种机制是由铁中心和碱性亚氨基配体的协同作用实现的。正如烯丙基质子的 p K a所指示的，该催化剂能够在含有多个 1-烯烃的底物中实现 C=C 双键的区域选择性转座。配合物的高自旋 ( S = 2) 状态允许广泛
• Functionalized organolithium reagents. 9. Lithiation and isomerization of allylic amines as a general route to enamines and their carbonyl derivatives
  作者：John J. Eisch、Jamshed H. Shah

  DOI：10.1021/jo00009a005

  日期：1991.4

  [3-(Diphenylamino)-2-propenyl]lithium, readily prepared by the lithiation of allyldiphenylamine with n-butyllithium in THF, undergoes alkylation either with organic halides or with carbonyl or azomethine derivatives to yield enamines, which can be converted by protons or other electrophiles into aldehydes or into five-membered heterocycles; lithiation of such allyldiarylamines with other reagents leads principally to isomerization to enamines (with lithium diisopropylamide) or to carbenoid intermediates (tert-butyllithium and potassium tert-butoxide).