(R)-N-(2-ethyl-6-methylphenyl)alanine | 82508-05-2

• 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: (R)-N-(2-ethyl-6-methylphenyl)alanine
• 英文别名: (R)-(+)-N-(2-Ethyl-6-methyl-phenyl)-alanin；N-(2-Ethyl-6-methylphenyl)-D-alanine；(2R)-2-(2-ethyl-6-methylanilino)propanoic acid
• CAS: 82508-05-2
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: ACQCQKSFTBFYDO-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-(2-ethyl-6-methylphenyl)alanine 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以96.8 g的产率得到(R)-(+)-N-(1'-Methyl-2'-hydroxyethyl)-2-ethyl-6-methylanilin
  参考文献：
  名称：

  Der Einfluß von Atropisomerie und chiralem Zentrum auf die biologische Aktivität des Metolachlor / Atropisomerism 和手性中心对 Metolachlor 生物活性的影响

  摘要：

  制备了草除草剂异丙甲草胺的四种立体异构体，其异构体基于手性中心和手性轴的组合，并通过X射线分析确定了它们的绝对构型。该合成是通过使用光学活性起始材料和新的光学活性氨基甲酸酯作为中间体来实现的。除草活性主要受手性中心的影响，S-异构体是最活跃的。

  DOI：

  10.1515/znb-1982-0411
• 作为产物：
  描述：

  N-(2-Ethyl-6-methyl-phenyl)-alaninmethylester 在 sodium hydroxide 作用下， 反应 6.0h， 以72.8 g的产率得到(R)-N-(2-ethyl-6-methylphenyl)alanine
  参考文献：
  名称：

  Der Einfluß von Atropisomerie und chiralem Zentrum auf die biologische Aktivität des Metolachlor / Atropisomerism 和手性中心对 Metolachlor 生物活性的影响

  摘要：

  制备了草除草剂异丙甲草胺的四种立体异构体，其异构体基于手性中心和手性轴的组合，并通过X射线分析确定了它们的绝对构型。该合成是通过使用光学活性起始材料和新的光学活性氨基甲酸酯作为中间体来实现的。除草活性主要受手性中心的影响，S-异构体是最活跃的。

  DOI：

  10.1515/znb-1982-0411

文献信息

• Chemoenzymatic synthesis of the chiral herbicide: (<i>S</i>)-metolachlor
  作者：Liangyu Zheng、Suoqin Zhang、Fang Wang、Gui Gao、Shugui Cao

  DOI：10.1139/v06-129

  日期：2006.8.1

  A chemoenzymatic approach for the production of (S)-metolachlor, one of the most widely used herbicides, has been developed. The starting material (S)-N-(2-ethyl-6-methylphenyl)alanine was obtained by the use of lipase-catalyzed hydrolytic kinetic resolution. Under the optimal conditions, the good activity and excellent enantioselectivity of lipase B from Candida antarctica (CAL-B,E > 100) are achieved in diethyl ether – water (15% v/v), which is about 9.7-fold more enantioselective than that in a pure buffered aqueous solution (E = 12.1). After a simple extraction procedure is used to separate the acid product from the remaining ester, the remaining ester is racemized, providing the basis for the continuous resolution process. Then (S)-metolachlor is synthesized by a simple chemical method using the enantiomerically pure (S)-acid.Key words: (S)-metolachlor, herbicide, CAL-B, (S)-N-(2-ethyl-6-methylphenyl)alanine, resolution.

  我们开发出了一种化学酶法生产(S)-甲草胺（最广泛使用的除草剂之一）的方法。起始原料(S)-N-(2-乙基-6-甲基苯基)丙氨酸是通过脂肪酶催化的水解动力学解析获得的。在最佳条件下，在二乙醚-水（15% v/v）中，来自南极念珠菌的脂肪酶 B（CAL-B,E >100）具有良好的活性和出色的对映选择性，其对映选择性比在纯缓冲水溶液（E = 12.1）中高出约 9.7 倍。使用简单的萃取程序将酸产物与剩余的酯分离后，剩余的酯发生消旋化，为连续解析过程奠定了基础。然后，利用对映体纯的(S)-酸，通过简单的化学方法合成了(S)-甲草胺。 关键词：(S)-甲草胺 除草剂 CAL-B (S)-N-(2-ethyl-6-methylphenyl)alanine 解析。
• MOSER, H.;RIHS, G.;SAUTER, H., Z. NATURFORSCH., 1982, 37, N 4, 451-462
  作者：MOSER, H.、RIHS, G.、SAUTER, H.

  DOI：——

  日期：——
• Der Einfluß von Atropisomerie und chiralem Zentrum auf die biologische Aktivität des Metolachlor / The Influence of Atropisomerism and Chiral Centre on the Biological Activity of Metolachlor
  作者：Hans Moser、Grety Rihs、Hanspeter Sauter

  DOI：10.1515/znb-1982-0411

  日期：1982.4.1

  stereoisomers of the grass herbicide Metolachlor, the isomerism of which is based on a combination of a chiral centre and a chiral axis, were prepared, and their absolute configurations determined by X-ray analysis. The synthesis was achieved by using optically active starting materials and new optically active carbamates as intermediates. The herbicidal activity is mainly influenced by the chiral centre, the

  制备了草除草剂异丙甲草胺的四种立体异构体，其异构体基于手性中心和手性轴的组合，并通过X射线分析确定了它们的绝对构型。该合成是通过使用光学活性起始材料和新的光学活性氨基甲酸酯作为中间体来实现的。除草活性主要受手性中心的影响，S-异构体是最活跃的。
• Enhancing lipase-catalyzed hydrolysis by adding macrocyclic tetraamines
  作者：Xuemei Tian、Kun Wu、Jin Tao、Liangyu Zheng、Suoqin Zhang、Shugui Cao

  DOI：10.1016/j.molcatb.2011.09.002

  日期：2012.1

  Macrocyclic tetraamines (MTs) were employed as novel additives to improve the enzyme's performance in Pseudomonas cepacia lipase (PCL)-catalyzed enantioselective hydrolysis of N-(2-ethyl-6-methylphenyl)alanine methyl ester (NEMPA-ME). Our results showed that the activity of PCL was significantly enhanced and the higher enantioselectivity of the reaction was maintained when some MTs were added to the reaction media. The acceleration of the initial reaction rate greatly depended on MT structure and additive concentration. Among the 21 MTs we tested, 10-(2-hydroxydecyl)-2, 6-dioxo-1,4,7,10-tetraazacyclododecane (MT#20) was found to be the best enzyme activator as 11-fold increase in the initial reaction rate was seen when an optimal concentration of 9.6 mmol/L of the amine was added. Kinetic analysis indicated that the affinity of lipase PCL toward the substrate was modified in the presence of MTs. Molecular modeling suggested that MTs could lead to a more native and stable conformation of lipase, thereby enhancing its enzymatic activity. This is the first systematic study of enhancement of an enzymatic reaction by MT-type additives. (C) 2011 Elsevier B.V. All rights reserved.