(S)-2-Acetylamino-3-p-tolyl-propionic acid | 74046-14-3

• 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-p-tolyl-propionic acid
• 英文别名: (2S)-2-acetamido-3-(4-methylphenyl)propanoic acid
• CAS: 74046-14-3
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: DTXURQXKJWPBIA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Acetylamino-3-p-tolyl-propionic acid 在 Acylase I enzyme from porcine kidney 、 水 作用下， 以72%的产率得到4-甲基-L-苯丙氨酸
  参考文献：
  名称：

  酰基转移酶I催化的水解对-取代的（小号） -苯丙氨酸衍生物由外消旋的混合物的邻-和对位-取代的异构体

  摘要：

  对位取代的（S）-苯丙氨酸可以通过用猪肾脏中的酰基转移酶I处理邻位和对位取代的N-乙酰基-（RS）-苯丙氨酸的相应混合物来获得。该酶的选择性可归因于其消化（S）-苯丙氨酸和（S）-酪氨酸的肽衍生物的进化。

  DOI：

  10.1016/s0040-4039(98)00997-6
• 作为产物：
  描述：

  N-acetyl-4-methyl-phenylalanine 在 phosphate buffer 、 acylase I from porcine kidney 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-2-Acetylamino-3-p-tolyl-propionic acid
  参考文献：
  名称：

  酰基转移酶I催化的水解对-取代的（小号） -苯丙氨酸衍生物由外消旋的混合物的邻-和对位-取代的异构体

  摘要：

  对位取代的（S）-苯丙氨酸可以通过用猪肾脏中的酰基转移酶I处理邻位和对位取代的N-乙酰基-（RS）-苯丙氨酸的相应混合物来获得。该酶的选择性可归因于其消化（S）-苯丙氨酸和（S）-酪氨酸的肽衍生物的进化。

  DOI：

  10.1016/s0040-4039(98)00997-6

文献信息

• 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。
• Novel atropisomeric bisphosphine ligands with a bridge across the 5,5′-position of the biphenyl for asymmetric catalysis
  作者：Hao Wei、Yong Jian Zhang、Feijun Wang、Wanbin Zhang

  DOI：10.1016/j.tetasy.2008.01.023

  日期：2008.3

  A new type of atropisomeric bisphosphine ligand 2 with a bridge across the 5,5'-position of the biphenyl has been developed. The axial chirality of this type of ligands can be retained by macrocyclic ring strain produced from 5,5'-linkage of the biphenyl even without 6,6'-substituents on the biphenyls. Ligand (R)-2a showed good catalytic activity and enantioselectivity for Rh(I)-catalyzed asymmetric hydrogenation of (Z)-alpha-acetamidocinnamic acid 11. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• Synthesis and application of peripherally alkyl-functionalized dendritic pyrphos ligands: Homogeneous-supported catalysts for enantioselective hydrogenation
  作者：Bing Yi、Hua-Ping He、Qing-Hua Fan

  DOI：10.1016/j.molcata.2009.09.004

  日期：2010.1

  A new series of dendritic ligands with a chiral diphosphine located at the focal point have been synthesized through coupling of (R, R)-3,4-bis(biphenylphosphino)pyrrolidine (pyrphos) with peripherally alkyl-functionalized benzoic acid dendrons. These ligands were employed in the Rh-catalyzed asymmetric hydrogenation of prochiral dehydroamino acids, exhibiting excellent catalytic activities and enantioselectivities. The second-generation dendritic catalyst could be recovered by simple liquid-liquid biphasic separation and reused four times without serious loss of its activity and selectivity. (C) 2009 Elsevier B.V. All rights reserved.
• H8-MonoPhos and its application in catalytic enantioselective hydrogenation of α-dehydroamino acids
  作者：Qingle Zeng、Hui Liu、Aiqiao Mi、Yaozhong Jiang、Xingshu Li、Michael C.K Choi、Albert S.C Chan

  DOI：10.1016/s0040-4020(02)01062-1

  日期：2002.10

  H-8-MonoPhos, a new stable and readily soluble monodentate phosphoramidite ligand, has been facilely prepared from H-8-BINOL. The ligand achieved up to 99.9% ee and 96.7% ee in hydrogenation of dehydroalanine and dehydrohomophenylalanine in a S/C ratio of 500:1, respectively, which are among the best results to date. For dehydrophenylalanine derivatives, it gave good to excellent enantioselectivity. Some factors controlling the enantioselectivity and conversion were examined and are discussed. The interesting effects of ligand/rhodium ratio on the enantioselectivity and conversion were observed, which a mechanism was proposed to explain. (C) 2002 Elsevier Science Ltd. All rights reserved.