ethyl (2R,3S)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate | 1310339-10-6

• 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,3S)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate
• 英文别名: ethyl 2-(benzamidomethyl)-3-hydroxyphenylpropanoate
• CAS: 1310339-10-6
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: SWGJBGURCZDYNU-IAGOWNOFSA-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：

  ethyl (2R,3S)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate 在 盐酸 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.08h， 生成 (3R)-1-[(4-bromophenyl)methyl]-3-[(R)-hydroxy(phenyl)methyl]azetidin-2-one
  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：

  苯甲酰乙酸乙酯 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 三氟化硼乙醚 、 C₃₇H₄₁FeN₂O₂PS 、 氢气 、 sodium carbonate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 45.0 ℃ 、3.55 MPa 条件下， 反应 26.0h， 生成 ethyl (2R,3S)-2-(benzamidomethyl)-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  铱催化的外消旋β'-酮-β-氨基酯的对映选择性和非对映选择性氢化通过动态动力学拆分

  摘要：

  报道了一种通过动态动力学拆分对α-取代的β-酮酯进行对映选择性氢化的铱/ f-二磷催化系统。期望的抗β”羟基β在中度至良好的产率（60-95％）与72-99％得到氨基酯EE秒和91：9到99：1个博士秒。该协议可以容忍各种官能团，并且可以轻松地以较低的催化剂负载量（TON 高达 9100）以克规模进行。

  DOI：

  10.1002/adsc.202100929

文献信息

• 一种(2R,3S)-β′-羟基-β-氨基酸酯类衍生物及其制备方法
  申请人：浙江工业大学

  公开号：CN113354554B

  公开（公告）日：2022-10-11

  本发明公开了一种(2R,3S)‑β′‑羟基‑β‑氨基酸酯类衍生物及其制备方法，所述制备过程为：在氩气氛围及0～60℃下，将金属Ir络合物与手性配体(III)加入到溶剂A中，搅拌反应0.5～6小时，制得金属Ir催化剂的溶剂A溶液；氮气保护下，往高压釜中依次加入β′‑羰基‑β‑氨基酸酯类衍生物、上述制备的金属Ir催化剂、溶剂B及碱A，于10～100℃温度和1.0～10.0MPa的氢气压力下反应2～24小时，反应结束后，减压浓缩除去溶剂，残留物经柱层析分离，得到(2R,3S)‑β′‑羟基‑β‑氨基酸酯类衍生物。本发明方法得到的β′‑羟基‑β‑氨基酸酯衍生物，反应收率高达95％，对映选择性高达99％，非对映选择性高达99∶1；与现有技术相比，具有原子经济性高、绿色污染小、易于工业化等特点。
• Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma
  作者：Martina Letizia Contente、Francesco Molinari、Paolo Zambelli、Valerio De Vitis、Raffaella Gandolfi、Andrea Pinto、Diego Romano

  DOI：10.1016/j.tetlet.2014.10.133

  日期：2014.12
• 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.
• Iridium‐Catalyzed Enantioselective and Diastereoselective Hydrogenation of Racemic <i>β’</i> ‐Keto‐ <i>β</i> ‐Amino Esters via Dynamic Kinetic Resolution
  作者：Fei Ling、Yifan Wang、An Huang、Ze Wang、Shiliang Wang、Jiayin He、Xianghua Zhao、Weihui Zhong

  DOI：10.1002/adsc.202100929

  日期：2021.10.19

  An iridium/f-diaphos catalytic system for the enantioselective hydrogenation of α-substituted β-ketoesters via dynamic kinetic resolution is reported. The desired anti β’-hydroxy-β-amino esters were obtained in moderate to good yields (60–95%) with 72–99% ees and 91:9 to 99:1 drs. This protocol tolerates various functional groups and could be easily conducted on gram scale with lower catalyst loading

  报道了一种通过动态动力学拆分对α-取代的β-酮酯进行对映选择性氢化的铱/ f-二磷催化系统。期望的抗β”羟基β在中度至良好的产率（60-95％）与72-99％得到氨基酯EE秒和91：9到99：1个博士秒。该协议可以容忍各种官能团，并且可以轻松地以较低的催化剂负载量（TON 高达 9100）以克规模进行。
• 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.