(S)-Dibenzylamino-phenyl-acetic acid benzyl ester | 192439-50-2

• 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: (S)-Dibenzylamino-phenyl-acetic acid benzyl ester
• 英文别名: benzyl (2S)-2-(dibenzylamino)-2-phenylacetate
• CAS: 192439-50-2
• 化学式: C₂₉H₂₇NO₂
• 分子量: 421.539
• InChiKey: SZQREMIIKFYHHF-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-Dibenzylamino-phenyl-acetic acid benzyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-(N,N-dibenzylamino)-2-phenylethanol
  参考文献：
  名称：

  手性N-杂环碳-铱配合物用于不对称还原前手性酮亚胺

  摘要：

  摘要使用一系列手性半三明治铱配合物，研究了亚胺对映体选择性还原为相应的手性仲胺。这些配合物中的手性N-杂环卡宾（NHC）配体是由易于获得的天然氨基酸合成的。廉价的苯基硅烷被用作方便的氢供体。在优化的条件下，Ir-NHC复合物可以降低酮亚胺的收率，尽管对映体过量（ee）适中。与由该系列其他NHC制备的催化剂相比，苯基甘氨酸衍生的手性NHC被证明可提供最佳的Ir催化剂，并且也可提供最大的ee。当使用带有基于缬氨酸的NHC的Ir配合物时，总是获得还原产物的相反对映异构体。

  DOI：

  10.1016/j.poly.2020.114976
• 作为产物：
  描述：

  L-苯甘氨酸 、 溴甲苯 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 (S)-Dibenzylamino-phenyl-acetic acid benzyl ester
  参考文献：
  名称：

  Diastereoselective reduction of β-ketophosphonates derived from amino acids. A new entry to enantiopure β-hydroxy-γ-aminophosphonate derivatives

  摘要：

  The reduction of gamma-N,N-dibenzylamino-beta-ketophosphonates 4 derived from readily available (S)-tribenzylated amino acids teas achieved with catecholborane at -20degreesC affording gamma-amino-beta-hydroxyphosphonates 5 in high diastereoselectivity and good chemical yield. These reactions provide a new entry to enantiomerically pure gamma-amino-beta-hydroxyphosphonates. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00159-3

文献信息

• Stereoselective Deprotonation of Chiral and Achiral 2-Aminoalkyl Carbamates: Synthesis of Optically Active β-Amino Alcohols via 1-Oxy-Substituted Alkyllithium Intermediates
  作者：Jörg Schwerdtfeger

  DOI：10.1055/s-1999-3575

  日期：1999.9
• A convenient synthesis of enaminones using tandem acetonitrile condensation, Grignard addition
  作者：Anthony R. Haight、Timothy L. Stuk、Jerome A. Menzia、Timothy A. Robbins

  DOI：10.1016/s0040-4039(97)00866-6

  日期：1997.6

  Condensations of N,N-dibenzyl alpha-amino esters with the anion of acetonitrile followed by the addition of a Grignard reagent proceed in excellent yields. This affords rapid access to the peptidomimetic precursor alpha-amino enaminones in one pot from the esters. (C) 1997 Elsevier Science Ltd.
• Stereoselective synthesis of β-amino alcohols: diastereoselective reduction of chiral α′-amino enones derived from amino acids
  作者：Sung-Kee Chung、Dong-Ho Kang

  DOI：10.1016/s0957-4166(97)00374-1

  日期：1997.9

  alpha-Amino acids are doubly benzylated at nitrogen to give N,N-dibenzyl amino adds, which can readily be converted to alpha'-amino enones 3. The alpha'-amino enones are very resistant to racemization, and undergo highly diastereoselective reduction to afford chiral amino alcohols upon treatment with L-Selectride under non-chelation control. (C) 1997 Elsevier Science Ltd.
• Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines
  作者：Lakshay Kathuria、Ashoka G. Samuelson

  DOI：10.1016/j.poly.2020.114976

  日期：2021.2

  phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands

  摘要使用一系列手性半三明治铱配合物，研究了亚胺对映体选择性还原为相应的手性仲胺。这些配合物中的手性N-杂环卡宾（NHC）配体是由易于获得的天然氨基酸合成的。廉价的苯基硅烷被用作方便的氢供体。在优化的条件下，Ir-NHC复合物可以降低酮亚胺的收率，尽管对映体过量（ee）适中。与由该系列其他NHC制备的催化剂相比，苯基甘氨酸衍生的手性NHC被证明可提供最佳的Ir催化剂，并且也可提供最大的ee。当使用带有基于缬氨酸的NHC的Ir配合物时，总是获得还原产物的相反对映异构体。
• Diastereoselective reduction of β-ketophosphonates derived from amino acids. A new entry to enantiopure β-hydroxy-γ-aminophosphonate derivatives
  作者：Mario Ordóñez、Ricardo de la Cruz、Mario Fernández-Zertuche、Miguel-Ángel Muñoz-Hernández

  DOI：10.1016/s0957-4166(02)00159-3

  日期：2002.4

  The reduction of gamma-N,N-dibenzylamino-beta-ketophosphonates 4 derived from readily available (S)-tribenzylated amino acids teas achieved with catecholborane at -20degreesC affording gamma-amino-beta-hydroxyphosphonates 5 in high diastereoselectivity and good chemical yield. These reactions provide a new entry to enantiomerically pure gamma-amino-beta-hydroxyphosphonates. (C) 2002 Elsevier Science Ltd. All rights reserved.