(2,5-Dioxopyrrolidin-1-yl) 2-[1-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]cyclopentyl]acetate | 1337538-60-9

• 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: (2,5-Dioxopyrrolidin-1-yl) 2-[1-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]cyclopentyl]acetate
• CAS: 1337538-60-9
• 化学式: C₁₇H₂₀N₂O₈
• 分子量: 380.354
• InChiKey: VZFAHPOOOBQTRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 1,1-环戊烷二乙酸 在 吡啶 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(2,5-Dioxopyrrolidin-1-yl) 2-[1-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]cyclopentyl]acetate
  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

文献信息

• In Situ Formation of <i>N</i>-Trifluoroacetoxy Succinimide (TFA-NHS): One-Pot Formation of Succinimidyl Esters, <i>N</i>-Trifluoroacetyl Amino Acid Succinimidyl Esters, and <i>N</i>-Maleoyl Amino Acid Succinimidyl Esters
  作者：Nicholas M. Leonard、Jarmila Brunckova

  DOI：10.1021/jo201686e

  日期：2011.11.4

  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.