1-((1S,2R)-2-hydroxy-1-phenylpropyl)pyrrolidine-2,5-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((1S,2R)-2-hydroxy-1-phenylpropyl)pyrrolidine-2,5-dione
• 英文别名: 1-[(1S,2R)-2-hydroxy-1-phenylpropyl]pyrrolidine-2,5-dione
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: SWKRSHJOKFOMQU-NOZJJQNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2R)-1-phenylpropane-1,2-diol 在 氯化亚砜 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-((1S,2R)-2-hydroxy-1-phenylpropyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Nucleophilic Ring Opening of Cyclic 1,2-Sulfites with Nitrogen Nucleophiles. A Route to Enantiopure Benzylic Amino Alcohols.

  摘要：

  The reaction between cyclic 1,2-sulfites and two imide and two sulfonamide nucleophiles has been Investigated in order to develop a procedure for the enantioselective preparation of N-protected vicinal amino alcohols. The results show that both imide and sulfonamide anions react with cyclic sulfites, yielding the desired products. In some cases the regioselectivities are low, and for the sulfonamides products originating from nucleophilic addition to the sulfite sulfur are observed.

  DOI：

  10.3891/acta.chem.scand.52-1060

文献信息

• Nucleophilic Ring Opening of Cyclic 1,2-Sulfites with Nitrogen Nucleophiles. A Route to Enantiopure Benzylic Amino Alcohols.
  作者：Kirsten Nymann、Saravanapavan Mylvaganam、John S. Svendsen、Inamur Rahaman Laskar、Nirmalendu Ray Chaudhuri、Kirsi Ranta、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1060

  日期：——

  The reaction between cyclic 1,2-sulfites and two imide and two sulfonamide nucleophiles has been Investigated in order to develop a procedure for the enantioselective preparation of N-protected vicinal amino alcohols. The results show that both imide and sulfonamide anions react with cyclic sulfites, yielding the desired products. In some cases the regioselectivities are low, and for the sulfonamides products originating from nucleophilic addition to the sulfite sulfur are observed.