(S)-2-pent-1-ynyl-1-((S)-2-trifluoromethylbenzenesulfinyl)piperidine | 944277-02-5

• 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: (S)-2-pent-1-ynyl-1-((S)-2-trifluoromethylbenzenesulfinyl)piperidine
• 英文别名: (2S)-2-pent-1-ynyl-1-[(S)-[2-(trifluoromethyl)phenyl]sulfinyl]piperidine
• CAS: 944277-02-5
• 化学式: C₁₇H₂₀F₃NOS
• 分子量: 343.413
• InChiKey: SNYZKJHZAHQBOQ-FATZIPQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-pent-1-ynyl-1-((S)-2-trifluoromethylbenzenesulfinyl)piperidine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以88%的产率得到(S)-2-pent-1-ynylpiperidine hydrochloride
  参考文献：
  名称：

  Asymmetric α-Alkynylation of Piperidine via N-Sulfinyliminium Salts

  摘要：

  Piperidine was stereoselectively alpha-alkynylated in a four-step sequence made up of transformation to a chiral nonracemic N-sulfinylpiperidine, anodic oxidation to N-sulfinyliminium ion equivalent, alkynylation through addition of a mixed organoaluminum derivative, and final acidic deprotection of the sulfoxide. Overall yields are around 50%, and the diastereoselectivity of the nucleophilc addition was between 92 and 99% de, allowing isolation of the final product with 99% enantiomeric purity.

  DOI：

  10.1021/jo070631c
• 作为产物：
  描述：

  2-Methoxy-1-((S)-2-trifluoromethyl-benzenesulfinyl)-piperidine 、 1-pentynyldimethylalane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以92%的产率得到(S)-2-pent-1-ynyl-1-((S)-2-trifluoromethylbenzenesulfinyl)piperidine
  参考文献：
  名称：

  Asymmetric α-Alkynylation of Piperidine via N-Sulfinyliminium Salts

  摘要：

  Piperidine was stereoselectively alpha-alkynylated in a four-step sequence made up of transformation to a chiral nonracemic N-sulfinylpiperidine, anodic oxidation to N-sulfinyliminium ion equivalent, alkynylation through addition of a mixed organoaluminum derivative, and final acidic deprotection of the sulfoxide. Overall yields are around 50%, and the diastereoselectivity of the nucleophilc addition was between 92 and 99% de, allowing isolation of the final product with 99% enantiomeric purity.

  DOI：

  10.1021/jo070631c