bis(2,2,2-trichloroethyl) 1-{1-(t-butoxycarbonyl)pyrrolidin-2-yl}hydrazine-1,2-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: bis(2,2,2-trichloroethyl) 1-{1-(t-butoxycarbonyl)pyrrolidin-2-yl}hydrazine-1,2-dicarboxylate
• 英文别名: Tert-butyl 2-[2,2,2-trichloroethoxycarbonyl-(2,2,2-trichloroethoxycarbonylamino)amino]pyrrolidine-1-carboxylate；tert-butyl 2-[2,2,2-trichloroethoxycarbonyl-(2,2,2-trichloroethoxycarbonylamino)amino]pyrrolidine-1-carboxylate
• 化学式: C₁₅H₂₁Cl₆N₃O₆
• 分子量: 552.066
• InChiKey: JVTVYEPDBIDPDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  97.41
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  bis(2,2,2-trichloroethyl) 1-{1-(t-butoxycarbonyl)pyrrolidin-2-yl}hydrazine-1,2-dicarboxylate 在 四氯化钛 、 烯丙基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以38%的产率得到3,3-dimethylhexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one
  参考文献：
  名称：

  双(2,2,2-三氯乙基)偶氮二甲酸酯对胺衍生物的α-氧化及其产物作为亚胺离子等价物的应用

  摘要：

  Alpha-oxidation of amine derivatives by azodicarboxylate was examined. Among several azodicarboxylate esters and amides tested, bis(2,2,2-trichloroethyl) azodicarboxylate, that has highly electrophilic 2,2,2-trichloroethoxycarbonyl functional groups, was found to have excellent oxidation reactivity. Acylated or carbamoylated amines were suitable substrates for this reaction condition. Tertially amines could react in the same manner, but spontaneous elimination of hydrazinyl group occurred to give dimerized products. The reaction products were found to react with nucleophiles in the presence of Lewis or Bronsted acid catalyst. This strongly suggests that the reaction products, alpha-hydrazinated amine derivatives, might serve as carbonyl group equivalents, very useful intermediates in synthetic organic chemistry.

  DOI：

  10.3987/com-16-s(s)70
• 作为产物：
  描述：

  偶氮基二羧酸双(2,2,2-三氯乙酯) 、 1-Boc-四氢吡咯 以 苯 为溶剂， 反应 3.0h， 以68%的产率得到bis(2,2,2-trichloroethyl) 1-{1-(t-butoxycarbonyl)pyrrolidin-2-yl}hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  使用双(2,2,2-三氯乙基)偶氮二羧酸酯开发叔烷基胺的高效α-氧化方法

  摘要：

  An efficient alpha-oxidation of amines can be accomplished using bis(2,2,2-trichloroethyl) azodicarboxylate, which is more electrophilic than diethyl azodicarboxylate, often used in synthetic chemistry. N-Acetyl and N-tert-butoxycarbonylamines are good substrates for this alpha-oxidation, and in the case of N-phenylpyrrolidine an interesting dimerization reaction is followed by alpha-oxidation. The alpha-oxidation product can be transformed in the presence of nucleophiles and a Lewis acid to alpha-modified amines, presumably via an iminium intermediate.

  DOI：

  10.3987/com-13-s(s)108