6-((1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid | 1337538-58-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-((1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid
• CAS: 1337538-58-5
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: OJQOTQFEKVAFIP-HDJSIYSDSA-N

物化性质

• 熔点：
  145-148 °C(Solv: water (7732-18-5))
• 沸点：
  619.1±38.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  103.78
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 6-((1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid 在 吡啶 、 三氟乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  In Situ Formation of N-Trifluoroacetoxy Succinimide (TFA-NHS): One-Pot Formation of Succinimidyl Esters, N-Trifluoroacetyl Amino Acid Succinimidyl Esters, and N-Maleoyl Amino Acid Succinimidyl Esters

  摘要：

  A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.

  DOI：

  10.1021/jo201686e
• 作为产物：
  描述：

  trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid 在 三氟乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.34h， 生成 6-((1r,4r)-4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxamido)hexanoic acid
  参考文献：
  名称：

  In Situ Formation of N-Trifluoroacetoxy Succinimide (TFA-NHS): One-Pot Formation of Succinimidyl Esters, N-Trifluoroacetyl Amino Acid Succinimidyl Esters, and N-Maleoyl Amino Acid Succinimidyl Esters

  摘要：

  A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.

  DOI：

  10.1021/jo201686e