N-acetyl-α-(L)-phenylglycine ethyl ester

• 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: N-acetyl-α-(L)-phenylglycine ethyl ester
• 英文别名: N-Acetyl-L-α-phenylglycine ethyl ester；(S)-N-acetylphenylglycine ethyl ester；N-acetyl-L-phenylglycine ethyl ester；ethyl (2S)-2-acetamido-2-phenylacetate
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: ADQCYQILCVEXBK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-acetamido-3-ethoxy-3-oxopropanoic acid 在 水 、 三氟乙酸酐 作用下， 生成 N-acetyl-α-(L)-phenylglycine ethyl ester
  参考文献：
  名称：

  有机三乙酸铅与4-乙氧基羰基-2-甲基恶唑-5-酮的反应。α-芳基和α-乙烯基N-乙酰基甘氨酸乙酯的合成及其酶促拆分

  摘要：

  已经实现了对水分敏感化合物4-乙氧基羰基-2-甲基恶唑-5-酮的有效合成。该化合物在4-位用有机三乙酸铅进行高产率的芳基化和乙烯基化反应，得到在水中转化为α-芳基和α-乙烯基N-乙酰基甘氨酸乙酯的化合物。这些α-取代的甘氨酸衍生物可以通过相应的羧酸的酯基或酰胺官能团的酶水解以非常好的收率和高的对映体过量动力学地拆分。

  DOI：

  10.1016/0040-4039(94)88529-x

文献信息

• Diastereoselective Synthesis of Arylglycine Derivatives by Cationic Palladium(II)-Catalyzed Addition of Arylboronic Acids to <i>N</i>-<i>tert</i>-Butanesulfinyl Imino Esters
  作者：Huixiong Dai、Xiyan Lu

  DOI：10.1021/ol0711220

  日期：2007.8.1

  A cationic palladium-complex-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl iminoacetates to yield the optically active arylglycine derivatives with moderate to good yield and high diastereoselectivity was developed. This reaction provides a convenient and efficient method for the synthesis of arylglycine derivatives.

  开发了阳离子钯络合物催化的芳基硼酸加成到N-叔丁烷亚磺酰基亚氨基乙酸酯中，以中等到良好的产率和高的非对映选择性产生光学活性的芳基甘氨酸衍生物。该反应为合成芳基甘氨酸衍生物提供了方便而有效的方法。
• Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyloxazol-5-one. The synthesis of α-aryl and α-vinyl N-acetylglycine ethyl esters and their enzymic resolution
  作者：Jacqueline Morgan、John T. Pinhey

  DOI：10.1016/0040-4039(94)88529-x

  日期：1994.12

  An efficient synthesis of the moisture-sensitive compound, 4-ethoxycarbonyl-2-methyloxazol-5-one, has been achieved. This compound undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which in water are converted to α-aryl and α-vinyl N-acetylglycine ethyl esters. These α-substituted glycine derivatives may be kinetically resolved in very

  已经实现了对水分敏感化合物4-乙氧基羰基-2-甲基恶唑-5-酮的有效合成。该化合物在4-位用有机三乙酸铅进行高产率的芳基化和乙烯基化反应，得到在水中转化为α-芳基和α-乙烯基N-乙酰基甘氨酸乙酯的化合物。这些α-取代的甘氨酸衍生物可以通过相应的羧酸的酯基或酰胺官能团的酶水解以非常好的收率和高的对映体过量动力学地拆分。
• Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330
  作者：Selvaraj Stella、Anju Chadha

  DOI：10.1016/j.tetasy.2010.02.011

  日期：2010.3

  Whole cells of Candida parapsilosis ATCC 7330 were used for the resolution of N-acetyl amino acid esters. Excellent enantioselectivities (E = 40 to >500) were achieved for the resolution of N-protected protein and non-protein amino acid esters giving good yields (28-50%) and high enantiomeric excesses (up to >99%) for both enantiomers. (C) 2010 Elsevier Ltd. All rights reserved.
• Morgan, Jacqueline; Pinhey, John T.; Sherry, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1997, # 5, p. 613 - 619
  作者：Morgan, Jacqueline、Pinhey, John T.、Sherry, Christopher J.

  DOI：——

  日期：——