ethyl (2R,3R)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate | 1310339-15-1

• 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: ethyl (2R,3R)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate
• CAS: 1310339-15-1
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: SWGJBGURCZDYNU-SJORKVTESA-N

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：

  ethyl (2R,3R)-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 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 60.25h， 生成 ethyl (2R,3R)-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

• 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.
• 3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation
  作者：Isabella Rimoldi、Edoardo Cesarotti、Daniele Zerla、Francesco Molinari、Domenico Albanese、Carlo Castellano、Raffaella Gandolfi

  DOI：10.1016/j.tetasy.2011.03.007

  日期：2011.3

  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.