methyl 2-((4-(tert-butyl)phenyl)amino)-2-phenylacetate | 1253782-92-1

• 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 2-((4-(tert-butyl)phenyl)amino)-2-phenylacetate
• 英文别名: Methyl 2-(4-tert-butylanilino)-2-phenylacetate；methyl 2-(4-tert-butylanilino)-2-phenylacetate
• CAS: 1253782-92-1
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: AMJWYNOCCYQOBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  C₁₉H₂₁NO₂ 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 苯硅烷 、 水 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以86%的产率得到methyl 2-((4-(tert-butyl)phenyl)amino)-2-phenylacetate
  参考文献：
  名称：

  亚胺酯的 Umpolung 反应性：可见光介导的苯基硅烷和水对 α-芳基亚氨基酯的转移氢化

  摘要：

  证明了 α-芳基亚氨基酯的可见光介导的化学选择性转移氢化。该方法允许有效且实用地制备 α-氨基酸酯。通过 DFT 计算探讨了反应机理，氘化实验表明氘被有效地引入氨基酸酯中（D 比率高达 99%），从而实现了使用 D 2 O 作为廉价氘源获得氘代氨基酸的可行方法.

  DOI：

  10.1002/chem.202202460

文献信息

• TfOH-Catalyzed N–H Insertion of α-Substituted-α-Diazoesters with Anilines Provides Access to Unnatural α-Amino Esters
  作者：Sha Hu、Jiale Wu、Zuolin Lu、Jiaqi Wang、Yuan Tao、Meifen Jiang、Fener Chen

  DOI：10.1021/acs.joc.0c02588

  日期：2021.2.19

  time-economical TfOH-catalyzed N–H insertion between anilines and α-alkyl and α-aryl-α-diazoacetates provides a straightforward approach to access unnatural α-amino esters, which readily undergo various transformations and can thus be used for the synthesis of pharmaceutically relevant molecules. The α-amino esters were obtained in moderate to excellent yields.

  节省时间的TfOH催化的苯胺与α-烷基和α-芳基-α-二重氮乙酸酯之间的N–H插入提供了一种直接获得非天然α-氨基酯的直接方法，该酯易于经历各种转化，因此可用于合成药物相关分子 以中等至优异的产率获得了α-氨基酯。
• 一种氨基酸酯或氘代氨基酸酯类化合物的制备方法
  申请人：云南民族大学

  公开号：CN114436871A

  公开（公告）日：2022-05-06

  本发明公开了一种氨基酸酯或氘代氨基酸酯类化合物的制备方法，是以亚氨酸酯、硅烷、水或重水为起始原料，将光敏剂、有机溶剂加入至反应容器中，在蓝光照射下进行搅拌反应，TLC薄层色谱检测反应原料亚氨酸酯完全消失，停止搅拌后除去挥发性溶剂，用硅胶柱层析或中性氧化铝柱层析，再经减压浓缩得到目标氨基酸酯或氘代氨基酸酯类化合物。本发明首次以蓝光催化代替了传统的贵金属催化，以硅烷、水代替传统的氢源，实现了对亚氨酸酯类化合物的转移氢化，且以廉价的氘水为氘源，可以制备一系列的氘代氨基酸酯类化合物，从而大大降低了生产成本；本发明方法采用的催化条件温和、催化体系简单，反应选择性高，安全性高，合成效率高，值得推广应用。
• Glycoporphyrin Catalysts for Efficient C–H Bond Aminations by Organic Azides
  作者：Giorgio Tseberlidis、Paolo Zardi、Alessandro Caselli、Damiano Cancogni、Matteo Fusari、Luigi Lay、Emma Gallo

  DOI：10.1021/acs.organomet.5b00436

  日期：2015.8.10

  We report herein the synthesis of new glycoporphyrin ligands which bear a glucopyranoside derivative on each meso-aryl moiety of the porphyrin skeleton. The saccharide unit is directly conjugated to the porphyrin or a triazole spacer is placed between the carbohydrate and porphyrin ring. The obtained glycoporphyrin ligands were employed to synthesize cobalt(II), ruthenium(II), and iron(III) complexes which were tested as catalysts of C-H bond aminations by organic azides. Two of the synthesized complexes were very efficient in promoting catalytic reactions, and the results achieved indicated that ruthenium and iron complexes show an interesting complementary catalytic activity in several amination reactions. The eco-friendly iron catalyst displayed very good chemical stability in catalyzing the amination reaction for three consecutive runs without losing catalytic activity.
• Gold (I) catalysis of X–H bond insertions
  作者：Ian K. Mangion、Mark Weisel

  DOI：10.1016/j.tetlet.2010.08.038

  日期：2010.10

  The utility of gold catalysis for carbene X-H bond insertion chemistry is described for the first time, taking advantage of the unique reactivity of sulfoxonium ylides as metal carbene precursors. (C) 2010 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.