(S)-2-cyclohexylsulfonyl-N,N-dimethylpent-4-enamide | 670223-07-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-cyclohexylsulfonyl-N,N-dimethylpent-4-enamide
• 英文别名: (2S)-2-cyclohexylsulfonyl-N,N-dimethylpent-4-enamide
• CAS: 670223-07-1
• 化学式: C₁₃H₂₃NO₃S
• 分子量: 273.397
• InChiKey: JHJPJHXPFQRRJD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-cyclohexylsulfonyl-N,N-dimethylpent-4-enamide 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 生成 (3S,5R)-4,5-dihydro-3-cyclohexylsulfonyl-5-iodomethyl-2(3H)-furanone 、 (3S,5S)-4,5-dihydro-3-cyclohexylsulfonyl-5-iodomethyl-2(3H)-furanone
  参考文献：
  名称：

  Asymmetric Induction of the Iodolactonization Reaction of α-Sulfurated γ-Unsaturated Amides

  摘要：

  The 1,3-asymmetric iodolactonization reaction of enantiopure alpha-sulfurated gamma-unsaturated amides has been investigated. With sulfinyl and sulfonyl groups, a poorly stereoselective reaction was observed, whereas with a sulfanyl moiety, the diastereoselectivity can be high as 96:4. The role of the oxygen atom on the sulfur moiety is discussed.

  DOI：

  10.1021/jo035488b
• 作为产物：
  描述：

  (SS,2S)-2-cyclohexylsulfinyl-N,N-dimethylpent-4-enethioamide 在 Oxone 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (S)-2-cyclohexylsulfonyl-N,N-dimethylpent-4-enamide
  参考文献：
  名称：

  Asymmetric Induction of the Iodolactonization Reaction of α-Sulfurated γ-Unsaturated Amides

  摘要：

  The 1,3-asymmetric iodolactonization reaction of enantiopure alpha-sulfurated gamma-unsaturated amides has been investigated. With sulfinyl and sulfonyl groups, a poorly stereoselective reaction was observed, whereas with a sulfanyl moiety, the diastereoselectivity can be high as 96:4. The role of the oxygen atom on the sulfur moiety is discussed.

  DOI：

  10.1021/jo035488b

文献信息

• Asymmetric Induction of the Iodolactonization Reaction of α-Sulfurated γ-Unsaturated Amides
  作者：Virginie Blot、Vincent Reboul、Patrick Metzner

  DOI：10.1021/jo035488b

  日期：2004.2.1

  The 1,3-asymmetric iodolactonization reaction of enantiopure alpha-sulfurated gamma-unsaturated amides has been investigated. With sulfinyl and sulfonyl groups, a poorly stereoselective reaction was observed, whereas with a sulfanyl moiety, the diastereoselectivity can be high as 96:4. The role of the oxygen atom on the sulfur moiety is discussed.