benzyl N-[(1S)-2-anilino-2-oxo-1-phenylethyl]carbamate | 499782-23-9

• 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: benzyl N-[(1S)-2-anilino-2-oxo-1-phenylethyl]carbamate
• CAS: 499782-23-9
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: NEOGFQHQRXEINE-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1S)-2-anilino-2-oxo-1-phenylethyl]carbamate 在 氢溴酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (S)-2-amino-N,2-diphenylacetamide
  参考文献：
  名称：

  Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides

  摘要：

  A series of alpha-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)(2) catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.120
• 作为产物：
  描述：

  Cbz-L-苯甘氨酸 、 苯胺 在 吡啶 、 1-丙基磷酸酐 作用下， 以 乙酸乙酯 为溶剂， 以94%的产率得到benzyl N-[(1S)-2-anilino-2-oxo-1-phenylethyl]carbamate
  参考文献：
  名称：

  General and Scalable Amide Bond Formation with Epimerization-Prone Substrates Using T3P and Pyridine

  摘要：

  The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine has been developed for low-epimerization amide bond formation and implemented for the synthesis of a key intermediate to a glucokinase activator. This robust method is general for the coupling of various racemization-prone acid substrates and amines, including relatively non-nucleophilic anilines, and provides amides in high yields with very low epimerization. With easy reaction setup and product isolation, this protocol offers several practical and experimental benefits.

  DOI：

  10.1021/ol201875q