(S)-2-Acetylamino-3-(3-chloro-phenyl)-propionic acid | 197087-51-7

• 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)-2-Acetylamino-3-(3-chloro-phenyl)-propionic acid
• 英文别名: N-Acetyl-3-chloro-L-phenylalanine；(2S)-2-acetamido-3-(3-chlorophenyl)propanoic acid
• CAS: 197087-51-7
• 化学式: C₁₁H₁₂ClNO₃
• 分子量: 241.674
• InChiKey: HASYVZNBHCVMEA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-2-Acetylamino-3-(3-chloro-phenyl)-acrylic acid 在 nonane>⁺ 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 0.17h， 生成 (S)-2-Acetylamino-3-(3-chloro-phenyl)-propionic acid
  参考文献：
  名称：

  Novel Spiro Phosphinite Ligands and Their Application in Homogeneous Catalytic Hydrogenation Reactions

  摘要：

  DOI：

  10.1021/ja970955q

文献信息

• A comparison of the asymmetric hydrogenation catalyzed by rhodium complexes containing chiral ligands with a binaphthyl unit and those with a 5,5′,6,6′,7,7′,8,8′-octahydro-binaphthyl unit
  作者：Fu-Yao Zhang、Wai Him Kwok、Albert S.C. Chan

  DOI：10.1016/s0957-4166(01)00399-8

  日期：2001.9

  The chiral ligands H8–BINAPO and H8–BDPAB were synthesized by reacting chlorodiphenylphosphine with H8–BINOL and H8–BINAM, respectively. Applications of these ligands in the Rh-catalyzed enantioselective hydrogenation of a variety of (Z)-acetamido-3-arylacrylic acid methyl esters provided chiral amino acid derivatives with good to excellent enantioselectivities (H8–BINAPO: up to 84.0% e.e.; H8–BDPAB:

  通过使氯二苯基膦分别与H 8 -BINOL和H 8 -BINAM反应合成手性配体H 8 -BINAPO和H 8 -BDPAB 。这些配体在多种（Z）-乙酰氨基-3-芳基丙烯酸甲酯的Rh催化对映选择性氢化中的应用提供了具有良好至优异对映选择性的手性氨基酸衍生物（H 8 -BINAPO：高达84.0％ee; H 8 –BDPAB：ee高达97.1％）。在乙酰胺基丙烯酸的氢化中，当使用[Rh（H 8 -BDPAB）] +催化剂时，获得了99％ee 。[Rh（H 8）的催化活性和对映选择性-BINAPO）] +和[Rh（H 8 -BDPAB）] +明显优于使用相应的含BINAPO（最高64％ee）和BDPAB（最高92.6％ee）的铑催化剂获得的那些。
• Facile Synthesis of Chiral Diphosphine-Containing Multiple Dendrimeric Catalysts for Enantioselective Hydrogenation
  作者：Liwen Zhao、Ji Liu、Yu Feng、Yanmei He、Qinghua Fan

  DOI：10.1002/cjoc.201200648

  日期：2012.9

  PyrPhos‐functionalized codendrimers have been synthesized via a liquid‐phase strategy in high yields. The resulting dendrimeric PyrPhos ligands were purified by a simple solvent precipitation without the need for chromatographic separation, and well characterized by 1H, 13C and 31P NMR, MALDI‐TOF mass spectroscopy as well as elemental analysis. Their rhodium complexes were applied to the asymmetric hydrogenation of

  通过液相策略以高收率合成了一种新型的手性二膦PyrPhos功能化共聚酯。生成的树枝状PyrPhos配体通过简单的溶剂沉淀法纯化，无需进行色谱分离，并通过1 H，13 C和31 P NMR，MALDI-TOF质谱以及元素分析进行​​了很好的表征。他们的铑配合物用于α的不对称氢化乙酰胺基肉桂酸。获得了优异的对映选择性，这与使用相应的小分子催化剂的对映选择性相当。另外，这些共聚体催化剂表现出比具有位于聚（芳基醚）树突的焦点处或聚（丙烯亚胺）树状体的外围的Rh（PyrPhos）位点的树状聚合物催化剂更好的催化性能。
• A highly effective phosphinite ligand derived from D-mannitol for Rh-catalyzed asymmetric hydrogenation
  作者：Yixin Chen、Xingshu Li、Siu-kuen Tong、Michael C.K. Choi、Albert S.C. Chan

  DOI：10.1016/s0040-4039(98)02457-5

  日期：1999.1

  chiral phosphinite 1,2,5,6-di-isopropylidene-3,4-bis(diphenylphosphino)-D-mannitol was prepared and its rhodium complex was found to be an effective catalyst for the asymmetric hydrogenation of amidoacrylic acid and its derivatives with product ee's ranging from 90% to 97%.

  制备了一种新型的手性次膦酸酯1,2,5,6-二异亚丙基-3,4-双（二苯基膦基）-D-甘露醇，发现其铑配合物是酰胺基丙烯酸及其不对称加氢的有效催化剂。产品ee介于90％至97％之间的衍生产品。
• Synthesis of a novel spiro bisphosphinamidite ligand for highly enantioselective hydrogenation
  作者：Ching Wen Lin、Chi-Ching Lin、Louis F.-L. Lam、Terry T.-L. Au-Yeung、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2004.07.137

  日期：2004.9

  A novel chiral bisphosphinamidite ligand SpiroNP has been synthesized. The rhodium complex of this ligand has been found to be highly active and enantioselective in the asymmetric hydrogenation of (Z)-2-acetamidoacrylic acid derivatives and α,β-unsaturated carboxylic acid derivatives.

  合成了一种新型的手性双膦亚酰胺配体SpiroNP。已经发现该配体的铑配合物在（Z）-2-乙酰氨基丙烯酸衍生物和α，β-不饱和羧酸衍生物的不对称氢化中具有高活性和对映选择性。
• Synthesis of a novel spiro bisphosphinite ligand and its application in Rh-catalyzed asymmetric hydrogenation
  作者：Zhenqiu Guo、Xiaoyu Guan、Zhiyong Chen

  DOI：10.1016/j.tetasy.2006.01.021

  日期：2006.2

  A novel, chiral bisphosphinite ligand (R)-SpiroBIP has been synthesized. The rhodium complex of the ligand was found to be highly enantioselective in the asymmetric hydrogenation of alpha-dehydroamino acid derivatives. (c) 2006 Published by Elsevier ltd.