(E)-1,3-diphenyl-N,N-dipropylprop-2-en-1-amine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1,3-diphenyl-N,N-dipropylprop-2-en-1-amine
• 英文别名: (E,1S)-1,3-diphenyl-N,N-dipropylprop-2-en-1-amine
• 化学式: C₂₁H₂₇N
• 分子量: 293.452
• InChiKey: UFBLFQWAOWYJRX-ANUWBXLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (±)-反式-1,3-二苯基烯丙基乙酸酯 、 二正丙胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 2-[(2R,5S)-3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]oct-2-yloxy]-1,1'-binaphthyl-2'-yl (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (E)-1,3-diphenyl-N,N-dipropylprop-2-en-1-amine
  参考文献：
  名称：

  Phosphites and diamidophosphites based on mono-ethers of BINOL: a comparison of enantioselectivity in asymmetric catalytic reactions

  摘要：

  Novel P-monodentate phosphite-type ligands have been synthesized in one step from BINOL monotosylate and BINOL mono-(-)-menthylcarbonate. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate and up to 99% ee in Rh-catalyzed asymmetric addition of phenylboronic acid to cyclohex-2-enone. The influence of the structural modules such as the nature of phosphorus-containing ring or exocyclic substituent on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.092

文献信息

• Palladium-catalyzed allylic substitution assisted by 1,3,2-diazaphospholidine derivatives of (R,R)-N-naphthyltartarimide
  作者：K. N. Gavrilov、E. A. Rastorguev、S. V. Zheglov、N. N. Groshkin、V. E. Boyko、A. S. Safronov、P. V. Petrovskii、V. A. Davankov

  DOI：10.1007/s11172-010-0228-7

  日期：2010.6

  P,P-Bidentate diamidophosphite ligands containing the (3R,4R)-3,4-dioxy-1-(1-naphthyl)pyrrolidine-2,5-dione framework and 1,3,2-diazaphospholidine rings with the stereogenic P atoms were obtained. The use of these ligands provides up to 85% ee in Pd-catalyzed asymmetric amination of (E)-1,3-diphenylallyl acetate and up to 95% ee in its asymmetric alkylation with dimethyl malonate.

  获得了含有(3R,4R)-3,4-二氧基-1-(1-萘基)吡咯烷-2,5-二酮框架和带有立体 P 原子的 1,3,2- 二氮磷啶环的 P,P-二叉二磷酸配体。在 Pd 催化下，(E)-1,3-二苯基烯丙基乙酸酯的不对称胺化反应中，这些配体的ee值高达 85%，而在其与丙二酸二甲酯的不对称烷基化反应中，ee值高达 95%。
• The use of an ionic liquid in asymmetric catalytic allylic amination
  作者：Sergey E. Lyubimov、Vadim A. Davankov、Konstantin N. Gavrilov

  DOI：10.1016/j.tetlet.2006.02.085

  日期：2006.4

  Asymmetric amination of 1,3-diphenyl-2-propenyl acetate with di-n-propylamine catalysed by palladium/P∗-chiral diamidophosphites was carried out in [bdmim]BF4- ionic liquid, THF and CH2Cl2 with up to 90% ee. The catalyst can be reused three times without loss in enantioselectivity.

  在[bdmim] BF4-离子液体，THF和CH 2 Cl 2中，至多90进行钯/ P *-手性二氨基亚磷酸酯催化的1，3-二苯基-2-丙烯基乙酸乙烯酯与二正丙胺的不对称胺化反应％ee。该催化剂可以重复使用三次，而不会损失对映选择性。
• Phosphites and diamidophosphites based on mono-ethers of BINOL: a comparison of enantioselectivity in asymmetric catalytic reactions
  作者：Konstantin N. Gavrilov、Sergey V. Zheglov、Mariya N. Gavrilova、Ivan M. Novikov、Marina G. Maksimova、Nikolay N. Groshkin、Eugenie A. Rastorguev、Vadim A. Davankov

  DOI：10.1016/j.tet.2011.11.092

  日期：2012.2

  Novel P-monodentate phosphite-type ligands have been synthesized in one step from BINOL monotosylate and BINOL mono-(-)-menthylcarbonate. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate and up to 99% ee in Rh-catalyzed asymmetric addition of phenylboronic acid to cyclohex-2-enone. The influence of the structural modules such as the nature of phosphorus-containing ring or exocyclic substituent on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.