(+/-)-2-氯苯基甘氨酸甲酯盐酸盐 | 141109-17-3

• 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
• 中文名称: (+/-)-2-氯苯基甘氨酸甲酯盐酸盐
• 中文别名: DL-2-氯苯甘氨酸甲酯盐酸盐
• 英文名称: (+/-)-2-chlorophenylglycine methyl ester hydrochloride
• 英文别名: [1-(2-Chlorophenyl)-2-methoxy-2-oxoethyl]azanium;chloride；[1-(2-chlorophenyl)-2-methoxy-2-oxoethyl]azanium;chloride
• CAS: 141109-17-3
• 化学式: C₉H₁₀ClNO₂*ClH
• mdl: MFCD16661100
• 分子量: 236.098
• InChiKey: SUUNIMMHDPICBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (+/-)-2-氯苯基甘氨酸甲酯盐酸盐 在 吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 tetraphosphorus decasulfide 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 34.0h， 生成 2-[3-(2-chlorophenyl)pyrazin-2-yl]sulfanyl-N-phenyl-acetamide
  参考文献：
  名称：

  Discovery of novel 2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamides as potent HIV-1 inhibitors using a structure-based bioisosterism approach

  摘要：

  The present work is an extension of our ongoing efforts towards the development and identification of new molecules with anti-HIV activity which have previously led to the discovery of arylazolylthioacetanilides as highly active NNRTIs. In this article, a series of 2-2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamide derivatives were synthesized and evaluated for in vitro anti-HIV activity. Most of the tested compounds exhibited moderate activities against wild-type HIV-1. Among them, compound 6k showed significant activity against wild-type HIV-1 with an EC50 value of 1.7 mu M, along with moderate activity against wild-type reverse transcriptase (RT). The preliminary structure-activity relationship (SAR) and docking calculations of this new series of compounds were also investigated, which may help designing more potent molecules. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.058
• 作为产物：
  描述：

  o-chlorophenylglycine 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (+/-)-2-氯苯基甘氨酸甲酯盐酸盐
  参考文献：
  名称：

  Discovery of novel 2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamides as potent HIV-1 inhibitors using a structure-based bioisosterism approach

  摘要：

  The present work is an extension of our ongoing efforts towards the development and identification of new molecules with anti-HIV activity which have previously led to the discovery of arylazolylthioacetanilides as highly active NNRTIs. In this article, a series of 2-2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamide derivatives were synthesized and evaluated for in vitro anti-HIV activity. Most of the tested compounds exhibited moderate activities against wild-type HIV-1. Among them, compound 6k showed significant activity against wild-type HIV-1 with an EC50 value of 1.7 mu M, along with moderate activity against wild-type reverse transcriptase (RT). The preliminary structure-activity relationship (SAR) and docking calculations of this new series of compounds were also investigated, which may help designing more potent molecules. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.058

文献信息

• <i>tert</i>-Butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a green and chemoselective <i>N-tert</i>-butoxycarbonylation reagent
  作者：Fangyu Du、Qifan Zhou、Yang Fu、Hanqi Zhao、Yuanguang Chen、Guoliang Chen

  DOI：10.1039/c9nj00885c

  日期：——

  The use of tert-butyl(3-cyano-4,6-dimethylpyridin-2yl) carbonate as a chemoselective tert-butoxycarbonylation reagent for aromatic and aliphatic amines has been demonstrated (30 examples).

  使用tert-丁基(3-氰基-4,6-二甲基吡啶-2基)碳酸酯作为芳香族和脂肪族胺的化学选择性tert-丁氧羰基化试剂已经得到证明（30个示例）。
• A chiral cobalt(<scp>ii</scp>) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines
  作者：Baiwei Ma、Weiwei Luo、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c7cc01278k

  日期：——

  A highly efficient catalytic asymmetric Formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N,N'-dioxide/Co(BF4)2.6H2O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained...

  通过手性N，N'-二氧化物/Co(BF4)2.6H2O络合物实现了5-烷氧基恶唑与偶氮二羧酸酯化合物的高效催化不对称形式[3 + 2]环加成反应。获得了一系列多取代的1,2,4-三唑啉化合物。
• Umpolung of Imines Enables Catalytic Asymmetric Regio-reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins
  作者：Bin Feng、Liang-Qiu Lu、Jia-Rong Chen、Guoqiang Feng、Bin-Qing He、Bin Lu、Wen-Jing Xiao

  DOI：10.1002/anie.201802492

  日期：2018.5.14

  copper‐catalyzed regio‐reversed asymmetric [3+2] cycloaddition of iminoesters with nitroolefins is disclosed for the first time. This method enables the facile synthesis of polysubstituted chiral pyrrolidines bearing at least one chiral quaternary center in high yields with excellent regio‐, diastereo‐, and enantioselectivity. The application of chiral P,S ligands and the unique effect of α‐aryl groups

  首次公开了亚氨基酯与硝基烯烃的铜催化的区域反转的不对称[3 + 2]环加成反应。这种方法可以轻松合成具有至少一个手性季中心的多取代手性吡咯烷，并具有极高的区域，非对映和对映选择性。手性P，S配体的应用以及α-芳基对亚氨基酯的独特作用是该方法成功的关键。还证明了该反应的实用性和多功能性。
• Modular Synthesis of α-Aryl-α-Heteroaryl α-Amino Acid Derivatives via a Copper-Catalyzed Cross-Dehydrogenative-Coupling Reaction Using Air as the Sole Oxidant
  作者：Xiangxiang Kong、Jing Ren、Jinlong Li、Yu Liu、Kaizhi Li

  DOI：10.1021/acs.orglett.3c01934

  日期：2023.10.6

  copper-catalyzed cross-dehydrogenative-coupling (CDC) process of arylglycine derivatives with N-heteroarenes for the straightforward synthesis of α-aryl-α-heteroaryl α-amino acid scaffolds has been successfully developed. This protocol exhibits a broad substrate scope with good functional group compatibility by utilizing air as the sole oxidant. The use of the reaction is also displayed through the late-stage functionalization

  一种新型的铜催化芳基甘氨酸衍生物与N-杂芳烃的交叉脱氢偶联（CDC）工艺已成功开发，用于直接合成α-芳基-α-杂芳基α-氨基酸支架。该方案利用空气作为唯一的氧化剂，表现出广泛的底物范围和良好的官能团兼容性。该反应的用途还通过带有天然化合物或药物基序的芳基甘氨酸的后期功能化来展示。
• Isotopically Directed Symmetry Breaking and Enantioenrichment in Attrition-Enhanced Deracemization
  作者：James I. Murray、Jacob N. Sanders、Paul F. Richardson、K. N. Houk、Donna G. Blackmond

  DOI：10.1021/jacs.9b11422

  日期：2020.2.26

  The evolution of homochirality via attrition-enhanced deracemization (AED) of enantiomorphic solids is carried out using molecules that differ only in the isotopic composition of a phenyl group positioned remote from the chiral center. Enantioenrichment consistently favors the enantiomorph containing a deuterated phenyl group over the protio or C-13 version, and the protio version is consistently favored over the C-13 version. While these isotopic compounds exhibit identical crystal structures and solubilities, the trend in deracemization correlates with melting points. Understanding the origin of this isotope bias provides fundamental clues about overcoming stochastic behavior to direct the stereochemical outcome in attrition-enhanced deracemization processes. The energy required for breaking symmetry with chiral bias is compared for this near-equilibrium AED process and the far-from-equilibrium Soai autocatalytic reaction. Implications for the origin of biological homochirality are discussed.