N,N-diethyl-N-(3-phenylprop-1-enyl)amine | 143236-90-2

• 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,N-diethyl-N-(3-phenylprop-1-enyl)amine
• 英文别名: (E)-N,N-diethyl-3-phenylprop-1-en-1-amine
• CAS: 143236-90-2
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: RFUNAURFTAZDNY-XYOKQWHBSA-N

物化性质

• 沸点：
  290.4±19.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二苯亚甲基甘氨酸甲酯 、 N,N-diethyl-N-(3-phenylprop-1-enyl)amine 在 zinc trifluoromethanesulfonate 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以31%的产率得到2-(Benzhydrylidene-amino)-3-diethylamino-5-phenyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Direct Addition of Glycine Derivatives to Enamines

  摘要：

  在一定量的路易斯酸催化下，甘氨酸衍生物与烯胺的直接加成反应进展顺利，并以极高的产率得到相应的 α,β-二氨基酸衍生物。在这一反应中，烯胺最初作为碱，随后作为 C=N 亲电体。这是利用烯胺作为亚胺等价物进行曼尼希式反应的第一个实例。

  DOI：

  10.1246/cl.2005.268
• 作为产物：
  描述：

  苯丙醛 、 二乙胺 以 氯仿 为溶剂， 反应 1.0h， 生成 N,N-diethyl-N-(3-phenylprop-1-enyl)amine
  参考文献：
  名称：

  Highly Chemoselective Formation of Aldehyde Enamines under Very Mild Reaction Conditions

  摘要：

  Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.

  DOI：

  10.1021/jo0611061

文献信息

• Regio‐ and Enantioselective Formal Hydroamination of Enamines for the Synthesis of 1,2‐Diamines
  作者：Lu Yu、Peter Somfai

  DOI：10.1002/anie.201902642

  日期：2019.6.17

  The asymmetric formal hydroamination of enamines using a CuH catalyst is reported. The method provides a straightforward and efficient approach to the synthesis of chiral 1,2‐dialkyl amines in good yields with high levels of enantioselectivities for a broad range of substrates, and should have significant value for the preparation of molecules bearing a 1,2‐diamine motif.

  报道了使用CuH催化剂对烯胺进行不对称的正式加氢胺化。该方法为高收率的手性1,2-二烷基胺的合成提供了一种简单有效的方法，对各种底物都有很高的对映选择性，对于制备带有1,2-二甲基的分子应该具有重要的价值。二胺基序。
• Chemically labile stannylene-nitrogen bonds. The chemoselective and stereoselective synthesis of N,N-bis(trimethylsilyl)enamines and N,N-dialkylenamines
  作者：Cynthia Burnell-Curty、Eric J. Roskamp

  DOI：10.1021/jo00045a009

  日期：1992.9

  The chemoselective reaction of Sn[N(TMS)2]2 with primary aldehydes leads to the stereoselective synthesis of trans-N,N-bis(trimethylsilyl)enamines. More reactive Sn(NR2)2 (R = Et, iPr, or piperidine) can be generated in situ and then treated with aldehydes or ketones to give trans enamines.
• [EN] ENANTIOSELECTIVE AMINATION AND ETHERIFICATION___________________<br/>[FR] AMINATION ET ETHERIFICATION ENANTIOSELECTIVE
  申请人：UNIV YALE

  公开号：WO2004024684A2

  公开（公告）日：2004-03-25

  The present invention is directed to a catalyst composition, comprising: (1) a catalyst precursor having the general structure MSXn wherein M is a transition metal selected from the group consisting of iridium, molybdenum, and tungsten; S is a coordinating ligand; X is a counterion; and n is an integer from 0 to 5; and (2) a phosphoramidite ligand having the structure wherein O-Cn-O is an aliphatic or aromatic diolate and wherein R1, R2, R3 and R4 are selected from the group consisting of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted aliphatic groups, and combinations thereof, with the proviso that at least one of R1, R2, R3, or R4 must be a substituted or unsubstituted aryl or heteroaryl group. The present invention is also directed to activated catalysts made from the above catalyst composition, as well as methods of allylic amination and etherification using the above catalysts.
• Highly Chemoselective Formation of Aldehyde Enamines under Very Mild Reaction Conditions
  作者：Guillaume Bélanger、Michaël Doré,、Frédéric Ménard、Véronique Darsigny

  DOI：10.1021/jo0611061

  日期：2006.9.1

  Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.
• Direct Addition of Glycine Derivatives to Enamines
  作者：Jun Kobayashi、Yasuhiro Yamashita、Shu Kobayashi

  DOI：10.1246/cl.2005.268

  日期：2005.2

  Direct addition of glycine derivatives to enamines proceeded smoothly in the presence of a catalytic amount of a Lewis acid to afford the corresponding α,β-diamino acid derivatives in excellent yields. In this reaction, enamines would initially act as a base and subsequently as a C=N electrophile. This is the first example of Mannich-type reactions using enamines as imine equivalents.

  在一定量的路易斯酸催化下，甘氨酸衍生物与烯胺的直接加成反应进展顺利，并以极高的产率得到相应的 α,β-二氨基酸衍生物。在这一反应中，烯胺最初作为碱，随后作为 C=N 亲电体。这是利用烯胺作为亚胺等价物进行曼尼希式反应的第一个实例。