(S)-2-chloro-5-(1-methylpyrrolidin-2-yl)-3-((trimethylsilyl)-ethynyl)pyridin-4-ol | 1211961-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-chloro-5-(1-methylpyrrolidin-2-yl)-3-((trimethylsilyl)-ethynyl)pyridin-4-ol
• 英文别名: 2-chloro-5-[(2S)-1-methylpyrrolidin-2-yl]-3-(2-trimethylsilylethynyl)-1H-pyridin-4-one
• CAS: 1211961-44-2
• 化学式: C₁₅H₂₁ClN₂OSi
• 分子量: 308.883
• InChiKey: WTAOJHDLKLRAQI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  20
• 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：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-chloro-5-(1-methylpyrrolidin-2-yl)-3-((trimethylsilyl)-ethynyl)pyridin-4-ol 在 copper(l) iodide 、 三乙胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以27%的产率得到4,4'-dichloro-7,7'-bis((S)-1-methylpyrrolidin-2-yl)-2,2'-bifuro[3,2-c]pyridine
  参考文献：
  名称：

  Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine

  摘要：

  The synthesis of novel fused-ring bicyclic (4-6) and tricyclic(7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuo, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.

  DOI：

  10.1021/jo9026929
• 作为产物：
  描述：

  (S)-2-chloro-3-iodo-5-(1-methylpyrrolidin-2-yl)pyridin-4-ol 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到(S)-2-chloro-5-(1-methylpyrrolidin-2-yl)-3-((trimethylsilyl)-ethynyl)pyridin-4-ol
  参考文献：
  名称：

  Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine

  摘要：

  The synthesis of novel fused-ring bicyclic (4-6) and tricyclic(7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuo, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.

  DOI：

  10.1021/jo9026929

文献信息

• Synthesis of Fused-Ring Nicotine Derivatives from (<i>S</i>)-Nicotine
  作者：Pauline W. Ondachi、Daniel L. Comins

  DOI：10.1021/jo9026929

  日期：2010.3.5

  The synthesis of novel fused-ring bicyclic (4-6) and tricyclic(7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuo, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.