2-(N-(4-氯苯基)氨基)丙酸甲酯 | 123695-95-4

• 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
• 中文名称: 2-(N-(4-氯苯基)氨基)丙酸甲酯
• 英文名称: methyl 2-(N-(4-chlorophenyl)amino)propanoate
• 英文别名: methyl N-(4-chlorophenyl)alaninate；Alanine, N-(4-chlorophenyl)-, methyl ester；methyl 2-(4-chloroanilino)propanoate
• CAS: 123695-95-4
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: MMCACXQOJXOMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-(4-氯苯基)氨基)丙酸甲酯 在 lithium aluminium tetrahydride 作用下， 生成 2-(2-chlorophenylamino)propan-1-ol
  参考文献：
  名称：

  Nishiyama, Tomihiro; Takahama, Yasumitsu; Yamada, Fukiko, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 195 - 197

  摘要：

  DOI：
• 作为产物：
  描述：

  丙酮酸甲酯 、 对氯苯胺 在 palladium on activated charcoal 氢气 、 sodium sulfate 作用下， 以 环己烷 为溶剂， 以67%的产率得到2-(N-(4-氯苯基)氨基)丙酸甲酯
  参考文献：
  名称：

  苯胺的催化还原性N-烷基化。在合成N-芳基氨基酸前体中的应用

  摘要：

  使用酮和α-酮酸酯作为烷基化剂，通过还原烷基化将不同的苯胺单烷基化，分离收率很好。这提供了获得氨基酸衍生物的途径。还进行了非对映选择性实验。

  DOI：

  10.1016/0040-4020(96)00503-0

文献信息

• Catalytic Enantioselective Synthesis of N,C^α,C^α-Trisubstituted α-Amino Acid Derivatives Using 1<i>H</i>-Imidazol-4(5<i>H</i>)-ones as Key Templates
  作者：Julen Etxabe、Joseba Izquierdo、Aitor Landa、Mikel Oiarbide、Claudio Palomo

  DOI：10.1002/anie.201501275

  日期：2015.6.1

  1H‐Imidazol‐4(5H)‐ones are introduced as novel nucleophilic α‐amino acid equivalents in asymmetric synthesis. These compounds not only allow highly efficient construction of tetrasubstituted stereogenic centers, but unlike hitherto known templates, provide direct access to N‐substituted (alkyl, allyl, aryl) α‐amino acid derivatives.

  在不对称合成中，将1 H-咪唑-4（5 H）-1作为新的亲核α-氨基酸等效物引入。这些化合物不仅可以高效地构建四取代的立体异构中心，而且与迄今已知的模板不同，可以直接获得N-取代的（烷基，烯丙基，芳基）α-氨基酸衍生物。
• Enantioselective Hydrolysis of Some 2-Aryloxyalkanoic Acid Methyl Esters and Isosteric Analogues Using a Penicillin G Acylase-Based HPLC Monolithic Silica Column
  作者：Gabriella Massolini、Enrica Calleri、Antonio Lavecchia、Fulvio Loiodice、Dieter Lubda、Caterina Temporini、Giuseppe Fracchiolla、Paolo Tortorella、Ettore Novellino、Gabriele Caccialanza

  DOI：10.1021/ac0204193

  日期：2003.2.1

  A technique based on liquid chromatography has been developed to facilitate studies of enantioselectivity in penicillin G acylase (PGA)-catalyzed hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues. PGA was covalently immobilized on an aminopropyl monolithic silica support to create an immobilized HPLC-enzyme reactor. Two sets of experimental data were drawn to calculate the enantioselectivity (E) of the kinetically controlled enantiomer-differentiating reaction, the degree of substrate conversion and the enantiomeric excess of the product. The developed enzymatic reactor was coupled through a switching valve to an achiral analytical column for separation and quantitation of the hydrolysis products. The enantiomeric excess was determined off-line on a PGA-chiral stationary phase. In this way, highly precise E values were determined. A computational study related to the hydrolysis of the considered racemic esters was also carried out in order to unambiguously clarify both the substrate specificity and the enantioselectivity displayed by PGA.

  一种基于液相色谱的技术已被开发出来，以便于研究青霉素G酰化酶（PGA）催化某些2-芳氧烷基酸甲酯及其同效物的水解反应中的对映选择性。PGA被共价固定在氨丙基单体硅胶支撑物上，创建了一个固定化HPLC-酶反应器。通过两组实验数据，计算了动力学控制的对映体区分反应的对映选择性（E）、底物转化率以及产物的对映过量。所开发的酶反应器通过切换阀与无手性的分析柱连接，用于分离和定量水解产物。对映过量在线上通过PGA-手性固定相确定。通过这种方式，获得了高度精确的E值。此外，还进行了与所考虑的外消旋酯水解相关的计算研究，以明确PGA所表现出的底物特异性和对映选择性。
• Synthesis, Fungicidal Activity and Plant Protective Properties of 1,2,3-Thiadiazole and Isothiazole-Based N-acyl-N-arylalaninates
  作者：Tatiana A. Kalinina、Valeriya I. Balandina、Konstantin L. Obydennov、Pavel A. Slepukhin、Zhijin Fan、Vasiliy A. Bakulev、Tatiana V. Glukhareva

  DOI：10.3390/molecules28010419

  日期：——

  The addition of active groups of known fungicides, or systemic acquired resistance inducers, into novel compound molecules to search for potential antifungal compounds is a popular and effective strategy. In this work, a new series of N-acyl-N-arylalanines was developed and synthesized, in which 1,2,3-thiadiazol-5-ylcarbonyl or 3,4-dichloroisothiazol-5-ylcarbonyl (fragments from synthetic plant resistance activators tiadinil and isotianil, respectively) and a fragment of N-arylalanine, the toxophoric group of acylalanine fungicides. Several new synthesized compounds have shown moderate antifungal activity against fungi in vitro, such as B. cinerea, R. solani and S. sclerotiorum. In vivo tests against A. brassicicola showed that compound 1d was 92% effective at a concentration of 200 µg/mL, similar to level of tiadinil, a known inducer of systemic resistance. Thus, 1d could be considered a new candidate fungicide for further detailed study. The present results will advance research and influence the search for more promising fungicides for disease control in agriculture.

  在新型化合物分子中加入已知杀真菌剂或系统获得性抗性诱导剂的活性基团，以寻找潜在的抗真菌化合物，是一种流行而有效的策略。这项研究开发并合成了一系列新的 N-酰基-N-芳基丙氨酸，其中包括 1,2,3-噻二唑-5-基羰基或 3,4-二氯异噻唑-5-基羰基（分别来自合成植物抗性激活剂噻菌胺和异噻菌胺的片段）和 N-芳基丙氨酸的一个片段，这是酰基丙氨酸类杀菌剂的毒力基团。几种新合成的化合物在体外对真菌（如 B.cinerea、R.solani 和 S.sclerotiorum）显示出中等程度的抗真菌活性。针对黄铜菌的体内测试表明，化合物 1d 在 200 µg/mL 浓度下的有效率为 92%，与噻菌胺（一种已知的系统抗性诱导剂）的水平相似。因此，1d 可被视为一种新的候选杀菌剂，有待进一步详细研究。本研究结果将推动相关研究，并影响寻找更多有前景的杀菌剂来控制农业病害。
• Study on the Design, Synthesis, Bioactivity and Translocation of the Conjugates of Phenazine-1-carboxylic Acid and N-Phenyl Alanine Ester
  作者：Yiran Wu、Guoqing Mao、Gaoshan Xing、Yao Tian、Yong Hu、Changzhou Liao、Li Li、Xiang Zhu、Junkai Li

  DOI：10.3390/molecules29081780

  日期：——

  phenazine-1-carboxylic acid (PCA) is known to lack phloem mobility, whereas Metalaxyl is a representative phloem systemic fungicide. In order to endow PCA with phloem mobility and also enhance its antifungal activity, thirty-two phenazine-1-carboxylic acid-N-phenylalanine esters conjugates were designed and synthesized by conjugating PCA with the active structure N-acylalanine methyl ester of Metalaxyl. All

  已知天然农药吩嗪-1-羧酸（PCA）缺乏韧皮部迁移性，而甲霜灵是一种代表性的韧皮部内吸性杀菌剂。为了赋予PCA韧皮部迁移性并增强其抗真菌活性，通过将PCA与甲霜灵活性结构N-酰基丙氨酸甲酯缀合，设计并合成了32种吩嗪-1-羧酸-N-苯丙氨酸酯缀合物。所有目标化合物均通过 1H NMR、13C NMR 和 HRMS 进行表征。抗真菌评价结果表明，几种目标化合物对核盘菌、大豆疫霉、寄生疫霉、柑橘疫霉表现出中度至强效的抗真菌活性。特别是，化合物F7对核盘菌表现出优异的抗真菌活性，EC50值为6.57 µg/mL，优于甲霜灵。蓖麻子系统中的韧皮部迁移性研究表明目标化合物 F1-F16 具有良好的韧皮部迁移性。特别是，化合物F2表现出优异的韧皮部迁移性；蓖麻子韧皮部汁液中化合物F2的含量为19.12μmol/L，是甲霜灵（3.56μmol/L）的6倍。不同pH培养液下的韧皮部迁移率测试验证了与“离子
• COMPOUNDS FOR USE IN TREATING NEUROMUSCULAR DISORDERS
  申请人：NMD Pharma A/S

  公开号：EP3307262B1

  公开（公告）日：2021-05-19