(2S,5S)-2,5-diethyltetrahydrothiophene | 1451012-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (2S,5S)-2,5-diethyltetrahydrothiophene
• 英文别名: (2S,5S)-2,5-diethylthiolane
• CAS: 1451012-47-7
• 化学式: C₈H₁₆S
• 分子量: 144.281
• InChiKey: XQKZIDUXMNZJJF-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2,5-diethyltetrahydrothiophene 、 氯化锑(V) 、 一氯化碘 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以70%的产率得到(2S,5S)-2,5-diethyl-1-iodotetrahydrothiophenium hexachloroantimonate
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865
• 作为产物：
  描述：

  (3S,6S)-3,6-辛二醇 在 sodiumsulfide nonahydrate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 (2S,5S)-2,5-diethyltetrahydrothiophene
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865