1-[(2-nitroethyl)sulfanyl]cyclohexane | 1571142-83-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-[(2-nitroethyl)sulfanyl]cyclohexane
• 英文别名: 2-Nitroethylsulfanylcyclohexane
• CAS: 1571142-83-0
• 化学式: C₈H₁₅NO₂S
• 分子量: 189.279
• InChiKey: PLDXKCIHQGZNKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(2-nitroethyl)sulfanyl]cyclohexane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到1-[(2-nitroethyl)sulfinyl]cyclohexane
  参考文献：
  名称：

  Chiral non-racemic sulfoxides by asymmetric alkylation of alkanesulfenates in the presence of a chiral ammonium phase-transfer catalyst derived from Cinchona alkaloid

  摘要：

  Based on a previous study involving arenesulfenates, the enantioselective S-alkylation of benzyl and alkyl sulfenates (RSO-)-S-1 wth alkyl halides, mediated by a cinchonidinium phase-transfer catalyst, was evaluated as a conceptually different synthetic approach to chiral sulfoxides. Direct application of our standard organocatalytic protocol, with methyl iodide as the electrophile, was rather disappointing mainly as a result of a sluggish release of the sulfur nucleophiles. However, slight modifications of the reaction conditions allowed the isolation of (R)-benzyl methyl sulfoxide in a 60% yield and a 38% ee, whereas (R)-cyclohexyl methyl sulfoxide was produced in a 34% yield and a 47% ee.[GRAPHICS].

  DOI：

  10.1080/17415993.2013.795226
• 作为产物：
  描述：

  环己硫醇 、 2-nitroethyl acetate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到1-[(2-nitroethyl)sulfanyl]cyclohexane
  参考文献：
  名称：

  Chiral non-racemic sulfoxides by asymmetric alkylation of alkanesulfenates in the presence of a chiral ammonium phase-transfer catalyst derived from Cinchona alkaloid

  摘要：

  Based on a previous study involving arenesulfenates, the enantioselective S-alkylation of benzyl and alkyl sulfenates (RSO-)-S-1 wth alkyl halides, mediated by a cinchonidinium phase-transfer catalyst, was evaluated as a conceptually different synthetic approach to chiral sulfoxides. Direct application of our standard organocatalytic protocol, with methyl iodide as the electrophile, was rather disappointing mainly as a result of a sluggish release of the sulfur nucleophiles. However, slight modifications of the reaction conditions allowed the isolation of (R)-benzyl methyl sulfoxide in a 60% yield and a 38% ee, whereas (R)-cyclohexyl methyl sulfoxide was produced in a 34% yield and a 47% ee.[GRAPHICS].

  DOI：

  10.1080/17415993.2013.795226