(2S,3S)-3-methyl-2-[(3-phenyl-2-propynoyl)amino]pentanoic acid | 1103350-47-5

• 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: (2S,3S)-3-methyl-2-[(3-phenyl-2-propynoyl)amino]pentanoic acid
• 英文别名: (2S,3S)-3-methyl-2-(3-phenylprop-2-ynoylamino)pentanoic acid
• CAS: 1103350-47-5
• 化学式: C₁₅H₁₇NO₃
• mdl: MFCD21601846
• 分子量: 259.305
• InChiKey: UVYRVZPTTQTXEK-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-异亮氨酸 、 1-(1H-1,2,3-benzotriazol-1-yl)-3-phenyl-2-propyn-1-one 在 三乙胺 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 19.0h， 以70%的产率得到(2S,3S)-3-methyl-2-[(3-phenyl-2-propynoyl)amino]pentanoic acid
  参考文献：
  名称：

  Preparation and Synthetic Applications of N-(α,β-Unsaturated Acyl)-α-amino Acid Derivatives

  摘要：

  N-(alpha,beta-Unsaturated acyl)-alpha-amino acids, amides and esters are structural motifs of many biologically active natural products. An alternate and advantageous approach for the synthesis of N-(alpha,beta-unsaturated acyl)-alpha-amino acid derivatives is developed via acylation of unprotected alpha-amino acids with stable crystalline N-(alpha,beta-unsaturated acyl)benzotriazole. The proposed methodology provides a new synthesis for compound (9) which is a precursor to a novel cytotoxic agent.

  DOI：

  10.3987/com-08-s(f)109

文献信息

• Preparation and Synthetic Applications of N-(α,β-Unsaturated Acyl)-α-amino Acid Derivatives
  作者：Alan R. Katritzky、Reena Gyanda、Nabin K. Meher、Yuming Song

  DOI：10.3987/com-08-s(f)109

  日期：——

  N-(alpha,beta-Unsaturated acyl)-alpha-amino acids, amides and esters are structural motifs of many biologically active natural products. An alternate and advantageous approach for the synthesis of N-(alpha,beta-unsaturated acyl)-alpha-amino acid derivatives is developed via acylation of unprotected alpha-amino acids with stable crystalline N-(alpha,beta-unsaturated acyl)benzotriazole. The proposed methodology provides a new synthesis for compound (9) which is a precursor to a novel cytotoxic agent.