2-quinolinyl (R)-1-(2-pyridinyl)ethyl sulfide | 220212-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-quinolinyl (R)-1-(2-pyridinyl)ethyl sulfide
• 英文别名: 2-[(1R)-1-pyridin-2-ylethyl]sulfanylquinoline
• CAS: 220212-79-3
• 化学式: C₁₆H₁₄N₂S
• 分子量: 266.367
• InChiKey: XAJPWULYBTYSHC-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-quinolinyl (R)-1-(2-pyridinyl)ethyl sulfide 在 乙基溴化镁 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 4.0h， 生成 (R)-1-(2-pyridinyl)-1-(2-quinolinyl)ethane
  参考文献：
  名称：

  Stereospecific Substitution of 1-(2-Pyridinyl)ethyl Methanesulfonate with S- and O-Nucleophiles

  摘要：

  Nucleophilic substitution reactions of (S)- and (R)-1-(2-pyridinyl)ethyl methanesulfonate with S- and O-nucleophiles are described. The reaction of S-nucelophiles, such as aryl- and alkylthiols, and thioacetic acid, gave substituted sulfide and thioacetate with inversion of the configurations. For the reaction of O-nucleophiles, sodium phenoxides gave aryl ethers in good yields stereospecifically, but sodium alkoxide gave complex mixtures including racemic alkyl ether. Reactions with sodium carboxylate afforded the corresponding ester stereospecifically.

  DOI：

  10.3987/com-00-s(i)52
• 作为产物：
  描述：

  2-喹啉硫醇 、 (S)-1-(2-pyridinyl)ethyl methanesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以86%的产率得到2-quinolinyl (R)-1-(2-pyridinyl)ethyl sulfide
  参考文献：
  名称：

  Stereospecific Substitution of 1-(2-Pyridinyl)ethyl Methanesulfonate with S- and O-Nucleophiles

  摘要：

  Nucleophilic substitution reactions of (S)- and (R)-1-(2-pyridinyl)ethyl methanesulfonate with S- and O-nucleophiles are described. The reaction of S-nucelophiles, such as aryl- and alkylthiols, and thioacetic acid, gave substituted sulfide and thioacetate with inversion of the configurations. For the reaction of O-nucleophiles, sodium phenoxides gave aryl ethers in good yields stereospecifically, but sodium alkoxide gave complex mixtures including racemic alkyl ether. Reactions with sodium carboxylate afforded the corresponding ester stereospecifically.

  DOI：

  10.3987/com-00-s(i)52

文献信息

• Stereospecific Displacement of 1-(Pyridinyl)ethanols with Amines and Thiols <i>via</i> Methanesulfonate Esters; Asymmetric Synthesis of 1-(Pyridinyl)ethylamines and Sulfides
  作者：Jun'ichi Uenishi

  DOI：10.1055/s-1999-2564

  日期：1999.1