2-(p-nitrobenzyl)isothiazolidine 1-oxide | 146787-84-0

• 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: 2-(p-nitrobenzyl)isothiazolidine 1-oxide
• 英文别名: Isothiazolidine, 2-[(4-nitrophenyl)methyl]-, 1-oxide；2-[(4-nitrophenyl)methyl]-1,2-thiazolidine 1-oxide
• CAS: 146787-84-0
• 化学式: C₁₀H₁₂N₂O₃S
• 分子量: 240.283
• InChiKey: GCVINIUQJAIPJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  isothiazolidine 1-oxide 、 对硝基溴化苄 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 以6%的产率得到2-(p-nitrobenzyl)isothiazolidine 1-oxide
  参考文献：
  名称：

  Carbonyl addition and alkylation reactions of isothiazolidine 1-oxide, the sulfur analog of 2-pyrrolidone

  摘要：

  Isothiazolidine 1-oxide is the sulfur analog of 2-pyrrolidone. A series of reactions at both the nitrogen and the alpha-sulfinyl carbon have been carried out. N-Deprotonation under phase-transfer conditions in the presence of p-nitrobenzyl bromide gives 2-(p-nitrobenzyl)isothiazolidine 1-oxide, the first cyclic sulfinamide to be characterized by X-ray analysis. Other N-substituted derivatives are also described. The dianion formed using 2 equiv of alkyllithium undergoes stereoselective monosubstitution with ketones and benzyl chloride at the carbon alpha to the sulfinyl group. With benzophenone, the syn product predominates as shown by X-ray analysis. Acetone also gives the syn product; however, with benzyl chloride, the anti product predominates. Unlike open-chain sulfinamides, the presence of a hydroxyl substituent on the carbon beta to the sulfinyl group in cyclic sulfinamides does not facilitate thermal elimination Of SO2 at 153-degrees-C, even after 5 h.

  DOI：

  10.1021/jo00055a024