methyl 2-((4-methoxyphenyl)amino)-2-(naphthalen-2-yl)acetate | 1353873-69-4

• 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-methoxyphenyl)amino)-2-(naphthalen-2-yl)acetate
• 英文别名: Methyl 2-(4-methoxyanilino)-2-naphthalen-2-ylacetate；methyl 2-(4-methoxyanilino)-2-naphthalen-2-ylacetate
• CAS: 1353873-69-4
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: WCLFVFHPWIOCAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-((4-methoxyphenyl)amino)-2-(naphthalen-2-yl)acetate 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 2-苯基-2,3-二氢-1,3-苯并噻唑 、 氧气 、 copper dichloride 作用下， 以 1,2-二氯乙烷 、 均三甲苯 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 (+)-(4-methoxyphenylamino)naphthalen-2-ylacetic acid methyl ester
  参考文献：
  名称：

  α-芳基甘氨酸酯的好氧氧化还原脱硫

  摘要：

  已经描述了α-芳基甘氨酸酯的有效氧化还原脱硫。一锅法氧化还原工艺包括使用分子氧作为末端氧化剂的铜（II）催化和以苯并噻唑啉为氢化物供体的手性磷酸催化不对称转移氢化。该反应表现出良好的官能团耐受性，提供了一系列具有优异对映选择性的光学活性非天然α-芳基甘氨酸酯。

  DOI：

  10.1016/j.tetlet.2020.152107
• 作为产物：
  描述：

  (4-methoxy-phenylimino)-(naphthalen-2-yl)-acetic acid methyl ester 在 2-(4'-carboxyphenyl)benzothiazoline 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 28.0h， 以87%的产率得到methyl 2-((4-methoxyphenyl)amino)-2-(naphthalen-2-yl)acetate
  参考文献：
  名称：

  Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor

  摘要：

  A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline and benzothiazole by washing with aqueous basic solution. The present approach provides a convenient and straightforward access to various amines with broad substrate scope and in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.061

文献信息

• Nitrogen‐Doped Carbon Enables Heterogeneous Asymmetric Insertion of Carbenoids into Amines Catalyzed by Rhodium Nanoparticles
  作者：Ryusuke Masuda、Tomohiro Yasukawa、Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1002/anie.202102506

  日期：2021.6

  into N−H bonds cocatalyzed by chiral phosphoric acid. Nitrogen dopants played a crucial role in both catalytic activity and enantioselectivity while almost no catalysis was observed with Rh nanoparticles immobilized on supports without nitrogen dopants. Various types of chiral α-amino acid derivatives were synthesized in high yields with high enantioselectivities and NCI-Rh could be reused in seven

  稳定的多相催化剂体系的发展是实现可持续社会的关键。尽管金属纳米颗粒是坚固的物种，但是由于限制了激活金属纳米颗粒而不引起金属浸出的方法的限制，因此限制了它们对不对称催化的研究。我们开发了氮掺杂碳作为固体配体负载的Rh纳米颗粒催化剂（NCI-Rh），可与金属相互作用，将类胡萝卜素不对称地插入手性磷酸共催化的N-H键中。氮掺杂剂在催化活性和对映选择性中都起着至关重要的作用，而将Rh纳米颗粒固定在没有氮掺杂剂的载体上几乎没有催化作用。以高收率和高对映选择性合成了各种类型的手性α-氨基酸衍生物，NCI-Rh可重复使用七次。此外，我们证明了使用装有NCI-Rh的色谱柱进行相应的连续流动反应。通过NCI-Rh的再活化，可在90多个小时内有效地获得所需的产物，并且可以回收手性来源。
• Asymmetric Hydrogenation of α-Amino Esters into Optically Active β-Amino Alcohols through Dynamic Kinetic Resolution Catalyzed by Ruthenabicyclic Complexes
  作者：Hiroki Ishikawa、Taiga Yurino、Ryo Komatsu、Ming-Yuan Gao、Noriyoshi Arai、Taichiro Touge、Kazuhiko Matsumura、Takeshi Ohkuma

  DOI：10.1021/acs.orglett.3c00740

  日期：——

  Racemic α-substituted α-amino esters were hydrogenated into enantioenriched β-amino alcohols through dynamic kinetic resolution with chiral ruthenabicyclic complexes. The reaction was carried out with a substrate/catalyst molar ratio of 200–1000 under 15 atm of H2 at 25 °C to afford a variety of β-substituted β-aminoethanols in up to 96% ee (24 examples). The mechanistic studies including deuteration

  通过手性钌双环配合物的动态动力学拆分，将外消旋 α-取代的 α-氨基酯氢化为富含对映体的 β-氨基醇。在 15 atm H 2和 25 °C下，底物/催化剂摩尔比为 200–1000 的情况下进行反应，以提供高达 96% ee 的各种 β-取代的 β-氨基乙醇（24 个示例）。包括氘化实验在内的机理研究表明，该反应是通过 α-氨基乙酸酯中间体的 1,2-氢化物迁移到 α-羟基亚胺，然后亚氨基化合物不断还原，得到氨基醇产物。
• Rh-Catalyzed Asymmetric Hydrogenation of α-Aryl Imino Esters: An Efficient Enantioselective Synthesis of Aryl Glycine Derivatives
  作者：Gao Shang、Qin Yang、Xumu Zhang

  DOI：10.1002/anie.200601540

  日期：2006.9.25
• Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor
  作者：Chen Zhu、Takahiko Akiyama

  DOI：10.1016/j.tetlet.2011.11.061

  日期：2012.1

  A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline and benzothiazole by washing with aqueous basic solution. The present approach provides a convenient and straightforward access to various amines with broad substrate scope and in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Molecular iodine catalyzed transfer hydrogenation: reduction of aldimines, ketimines, and α-imino esters
  作者：Prabhakar Bachu、Chen Zhu、Takahiko Akiyama

  DOI：10.1016/j.tetlet.2013.05.071

  日期：2013.7

  An efficient and practical protocol for the reduction of aldimines, ketimines, and alpha-imino esters in the presence of catalytic amount of molecular iodine with Hantzsch ester at ambient temperature afforded the corresponding amines in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.