(S)-N-Boc-(2’-氯苯基)甘氨酸 | 225918-60-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: (S)-N-Boc-(2’-氯苯基)甘氨酸
• 中文别名: (S)-N-叔丁氧羰基-(2'-氯苯基)甘氨酸
• 英文名称: N-Boc-(S)-2-chlorophenylglycine
• 英文别名: (S)-N-Boc-(2'-Chlorophenyl)Glycine；(2S)-2-(2-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 225918-60-5
• 化学式: C₁₃H₁₆ClNO₄
• 分子量: 285.727
• InChiKey: XPFJZGJBRMTXCE-JTQLQIEISA-N

物化性质

• 沸点：
  431.5±40.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (S)-N-Boc-(2’-氯苯基)甘氨酸 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-2-氯苯甘氨酸
  参考文献：
  名称：

  Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel

  摘要：

  The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA (R)). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.040
• 作为产物：
  描述：

  N-benzyhydryl-(2-chlorobenzylidene)-amine 在 titanium(IV) isopropylate 、 盐酸 、 sodium hydroxide 、 C₂₄H₃₅Cl₂N₃O₆ 、 异丙醇 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 38.5h， 生成 (S)-N-Boc-(2’-氯苯基)甘氨酸
  参考文献：
  名称：

  Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids

  摘要：

  DOI：

  10.1021/ja9840605

文献信息

• A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction
  作者：Vorawit Banphavichit、Woraluk Mansawat、Worawan Bhanthumnavin、Tirayut Vilaivan

  DOI：10.1016/j.tet.2009.04.098

  日期：2009.7

  A practical procedure for catalytic asymmetric synthesis of optically active arylglycine derivatives via optically active α-aminonitriles has been developed. The N-benzhydryl α-arylaminonitrile intermediates were prepared in excellent yield (89–99%) and enantiomeric purity (96 to >98% ee) by enantioselective cyanation of aldimines with TMSCN/iPrOH in the presence of 2.5 mol % of an easily prepared

  已经开发了通过光学活性α-氨基腈催化不对称合成光学活性芳基甘氨酸衍生物的实用方法。所述Ñ在良好的产率（89-99％）和对映体纯度（96至> 98％ee）的通过与TMSCN /醛亚胺对映选择性氰化制备-二苯甲基α-arylaminonitrile中间体我PrOH中在2.5％（摩尔）的存在下很容易地在0°C下制备Ti /手性氨基醇络合物，而无需缓慢添加氰化剂。易消旋的α-氨基腈中间体被HCl / TFA水溶液有效水解，得到芳基甘氨酸衍生物，收率高（60-92％），对映体纯度中等至极好（ee 85-98％）。
• Chemo-Enzymatic Dynamic Kinetic Resolution of Amino Acid Thioesters
  作者：Dario Arosio、Antonio Caligiuri、Paola D'Arrigo、Giuseppe Pedrocchi-Fantoni、Cristina Rossi、Caterina Saraceno、Stefano Servi、Davide Tessaro

  DOI：10.1002/adsc.200700050

  日期：2007.6.4

  racemic-N-protected-β,γ-unsaturated α-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracemisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities

  发现外消旋-N-保护的β，γ-不饱和α-氨基酸硫代酯的L-形式是枯草杆菌蛋白酶催化水解成相应酸的底物。D-对映体在有机碱的存在下连续消旋。在双相系统中的合并的反应允许基于动态动力学拆分使氨基酸衍生物脱氨。获得了优异的产率和对映选择性。
• Copper-catalyzed enantioselective 1,4-hydroboration of α,β-unsaturated amides
  作者：Hong-Hao Yan、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tetlet.2023.154364

  日期：2023.3

  described a new catalytic system for copper-catalyzed asymmetric conjugate hydroboration of α,β-unsaturated amides. Under the optimal conditions, the reactions proceeded smoothly to afford the corresponding chiral β-hydroxyl amides with up to 96% yield and 84% ee by employing chiral N,P-ligand. The reaction conditions are mild, the operation is simple, and it has good substrate generality.

  手性硼酸盐可以进行各种具有高度立体特异性的转化，因此它们在不对称合成中具有重要意义。在此我们描述了一种新的催化体系，用于铜催化的 α,β-不饱和酰胺的不对称共轭硼氢化反应。在最佳条件下，反应顺利进行，通过使用手性 N,P-配体得到相应的手性 β-羟基酰胺，产率高达 96%，ee 率为 84%。反应条件温和，操作简单，底物通用性好。
• Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel
  作者：Patrizia Ferraboschi、Maria De Mieri、Fiorella Galimberti

  DOI：10.1016/j.tetasy.2010.06.040

  日期：2010.9

  The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA (R)). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation. (C) 2010 Elsevier Ltd. All rights reserved.
• Ti-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids
  作者：Clinton A. Krueger、Kevin W. Kuntz、Carolyn D. Dzierba、Wolfgang G. Wirschun、John D. Gleason、Marc L. Snapper、Amir H. Hoveyda

  DOI：10.1021/ja9840605

  日期：1999.5.1