(2S,3S)-ethyl 2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate | 1310339-16-2

• 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: (2S,3S)-ethyl 2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate
• 英文别名: ethyl (2S,3S)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate
• CAS: 1310339-16-2
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: SWGJBGURCZDYNU-DLBZAZTESA-N

物化性质

• 沸点：
  558.5±50.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-ethyl 2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate 在 盐酸 、 水 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 C₁₀H₁₃NO₃
  参考文献：
  名称：

  3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation

  摘要：

  The catalytic asymmetric reduction of ethyl-2-(benzamidomethyl)-3-oxo-phenylpropanoate was realized with high enantiomeric and diastereoisomeric excesses via biotransformation using whole cells of different yeasts and asymmetric hydrogenation with Ru(II) complexes prepared from different chiral diphosphine ligands.With these combined approaches it was possible to prepare both enantiomers of the syn-stereoisomers in almost enantiomerically pure form; one of the enantiomers of the anti-stereoisomer was obtained in high ee with selected yeast while the other enantiomer of the anti was prepared in low ee and de. With three of the four epimers we were able to prepare the corresponding azetidinones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.007
• 作为产物：
  描述：

  N-氯甲基-苯甲酰胺 在 (x)C₃H₇NO*C₃₆H₃₂P₂S₂*2Cl^(1-)*Ru⁽²⁺⁾ 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 60.0 ℃ 、5.07 MPa 条件下， 反应 72.25h， 生成 (2S,3S)-ethyl 2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation

  摘要：

  The catalytic asymmetric reduction of ethyl-2-(benzamidomethyl)-3-oxo-phenylpropanoate was realized with high enantiomeric and diastereoisomeric excesses via biotransformation using whole cells of different yeasts and asymmetric hydrogenation with Ru(II) complexes prepared from different chiral diphosphine ligands.With these combined approaches it was possible to prepare both enantiomers of the syn-stereoisomers in almost enantiomerically pure form; one of the enantiomers of the anti-stereoisomer was obtained in high ee with selected yeast while the other enantiomer of the anti was prepared in low ee and de. With three of the four epimers we were able to prepare the corresponding azetidinones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.007

文献信息

• Dynamic kinetic resolution of β′-keto-β-amino esters using Ru–DTBM–Sunphos catalyzed asymmetric hydrogenation
  作者：Xiaoming Li、Xiaoming Tao、Xin Ma、Wanfang Li、Mengmeng Zhao、Xiaomin Xie、Tahar Ayad、Virginie Ratovelomanana-Vidal、Zhaoguo Zhang

  DOI：10.1016/j.tet.2013.05.136

  日期：2013.8

  higher activity and selectivity than the corresponding [Ru(cymene)I2]2–Sunphos. In situ generated catalyst could be used for this transformation. Asymmetric hydrogenation of a series of β′-keto-β-amino esters derivatives using Ru–Sunphos complexes via dynamic kinetic resolution led to the corresponding β′-hydroxy-β-amino esters with ee up to 99.6% and de up to 98.8% (S/C=1000).

  通过深入研究反应条件，开发了一种方便的对映选择性合成β'-羟基-β-氨基酯的方法。发现二氯甲烷（DCM）/ 2,2,2-三氟乙醇（TFE）和1,2-二氯乙烷（DCE）/ TFE组合是该反应的合适助溶剂。在这种混合溶剂体系中，[Ru（cymene ）Cl 2 ] 2 -Sunphos的活性和选择性都比相应的[Ru（cymene）I 2 ] 2高。–Sunphos。原位产生的催化剂可用于该转化。使用Ru-Sunphos配合物通过动态动力学拆分对一系列β'-酮-β-氨基酯衍生物进行不对称加氢，导致相应的β'-羟基-β-氨基酯的ee高达99.6％，de高达98.8％ （S / C＝ 1000）。
• 8-Amino-5,6,7,8-tetrahydroquinolines as ligands in iridium(III) catalysts for the reduction of aryl ketones by asymmetric transfer hydrogenation (ATH)
  作者：Daniele Zerla、Giorgio Facchetti、Marco Fusè、Michela Pellizzoni、Carlo Castellano、Edoardo Cesarotti、Raffaella Gandolfi、Isabella Rimoldi

  DOI：10.1016/j.tetasy.2014.06.003

  日期：2014.7

  Aqua iridium(III) complexes with 8-amino-5,6,7,8-tetrahydroquinolines CAMPY L1 and its derivatives as chiral ligands proved to be very efficient catalysts for the reduction of a wide range of prochiral aryl ketones, revealing a variety of behaviours in terms of reaction rate and stereoselectivity. As standard substrates, differently substituted acetophenones were studied and good enantioselectivity (86% ee) was achieved in the reduction of 1-(o-tolyl)ethan-1-one 6. Particularly interesting was the ATH reaction in the case of beta-amino keto esters, precursors of beta-lactams and azetidinones. The best results were obtained with [Cp*Ir(H2O)(L1)]SO4 affording the corresponding diastereomeric alcohols in an (R,S)-configuration with an excellent 99% ee in the reduction of 2-(benzamido methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl) propanoate 12. (C) 2014 Elsevier Ltd. All rights reserved.