methyl 3-phenyl-2-{[4-(trifluoromethyl)phenyl]amino}propanoate | 1605291-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-phenyl-2-{[4-(trifluoromethyl)phenyl]amino}propanoate
• 英文别名: 2-(p-(Trifluoromethyl)anilino)-3-phenylpropionic acid methyl ester；methyl 3-phenyl-2-[4-(trifluoromethyl)anilino]propanoate
• CAS: 1605291-23-3
• 化学式: C₁₇H₁₆F₃NO₂
• 分子量: 323.315
• InChiKey: PWJBDIWPKXDKSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-benzyl-4-(trifluoromethyl)aniline 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 methyl 3-phenyl-2-{[4-(trifluoromethyl)phenyl]amino}propanoate
  参考文献：
  名称：

  N-苄基和N-烯丙基甘氨酸甲基酯的Aza-Wittig重排。令人惊讶的级联Aza-Wittig重排/加氢硼化反应的发现

  摘要：

  用n Bu 2 BOTf和i Pr 2 NEt处理N-（芳基甲基）-N-芳基或N-烯丙基-N-芳基甘氨酸甲酯衍生物会产生aza-Wittig重排，提供N-芳基苯丙氨酸甲酯衍生物和N -芳基烯丙基甘氨酸甲基酯衍生物，分别以高收率和中等至良好的非对映选择性而得到。在相似条件下，带有N-羰基的类似底物被转化为1,4,2-氧杂硼烷衍生物。另外，N-烯丙基-N-在升高的温度下经受类似条件的芳基甘氨酸甲酯衍生物进行aza- [2,3] -Wittig重排，然后进行随后的硼氢化氧化反应，得到取代的氨基醇产物。

  DOI：

  10.1021/acs.joc.5b01286

文献信息

• Transition Metal‐Free <i>N‐</i> Arylation of Amino Acid Esters with Diaryliodonium Salts
  作者：Gabriella Kervefors、Leonard Kersting、Berit Olofsson

  DOI：10.1002/chem.202005351

  日期：2021.3.26

  A transition metal‐free approach for the N‐arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional

  已经开发出一种用于氨基酸衍生物N芳基化的无过渡金属方法。该方法的关键是使用带有茴香基配体的不对称二芳基碘盐，这被证明对于获得高化学选择性和产率非常重要。范围包括缺电子、富电子和空间位阻芳基与各种不同官能团的转移。此外，环状二芳基碘鎓盐成功地用于芳基化。获得保留对映体过量的N-芳基化产物。
• Aza-[1,2]-Wittig rearrangements of N-benzyl glycine methyl esters. A new approach to the synthesis of N-aryl phenylalanine derivatives
  作者：Renata K. Everett、John P. Wolfe

  DOI：10.1016/j.tetlet.2015.01.037

  日期：2015.6

  Treatment of N-(arylmethyl)-N-aryl glycine methyl ester derivatives with Bu2BOTf and (Pr2NEt)-Pr-i effects an aza-[1,2]-Wittig rearrangement that provides N-aryl phenylalanine methyl esters in good yields. Analogous substrates bearing N-carbonyl groups are converted to 1,4,2-oxazaborole derivatives under similar conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Biologically Relevant Compounds by Ruthenium Porphyrin Catalyzed Amination of Benzylic C–H Bonds
  作者：Paolo Zardi、Alessandro Caselli、Piero Macchi、Francesco Ferretti、Emma Gallo

  DOI：10.1021/om500064d

  日期：2014.5.12

  Herein we report the catalytic activity of ruthenium porphyrin complexes to promote the amination of benzylic C-H bonds by aryl azides, yielding alpha- and beta-amino esters. The catalytic methodology is also effective to synthesize two derivatives of methyl L-3-phenyllactate in order to convert one of them into the corresponding beta-lactam. The catalytic experimental conditions have been optimized on the basis of a preliminary mechanistic investigation which underlines the pivotal role of the substrate concentration to maximize the reaction productivity.