2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl]-formylamino]acetic acid | 1067244-12-5

• 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: 2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl]-formylamino]acetic acid
• CAS: 1067244-12-5
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: QBEOYNJKAYYJJG-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl]-formylamino]acetic acid 、 t-butyl 2-isocyano-3-phenyl propionate 以 氯仿 为溶剂， 反应 0.5h， 以10 mg的产率得到tert-butyl (2S)-2-[[2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl]-formylamino]acetyl]-formylamino]-3-phenylpropanoate
  参考文献：
  名称：

  Addressing Mechanistic Issues in the Coupling of Isonitriles and Carboxylic Acids: Potential Routes to Peptidic Constructs

  摘要：

  Mechanistic issues surrounding the two component coupling (2CC) reaction of carboxylic acids with isonitriles have been investigated. Experimental details suggest the formimidate carboxylate mixed anhydride intermediate exists in both interdictable and noninterdictable form. Furthermore, the 2CC reaction has been applied to the synthesis of a tripeptide featuring two formyl functional groups.

  DOI：

  10.1021/ja804709s
• 作为产物：
  描述：

  tert-butyl 2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl]-formylamino]acetate 在 甲酸 作用下， 反应 4.0h， 生成 2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-4-methylpentanoyl]-formylamino]acetic acid
  参考文献：
  名称：

  Addressing Mechanistic Issues in the Coupling of Isonitriles and Carboxylic Acids: Potential Routes to Peptidic Constructs

  摘要：

  Mechanistic issues surrounding the two component coupling (2CC) reaction of carboxylic acids with isonitriles have been investigated. Experimental details suggest the formimidate carboxylate mixed anhydride intermediate exists in both interdictable and noninterdictable form. Furthermore, the 2CC reaction has been applied to the synthesis of a tripeptide featuring two formyl functional groups.

  DOI：

  10.1021/ja804709s