(1R,2R,4S)-1,3,3-Trimethyl-2-(6-methyl-pyridin-2-ylmethyl)-bicyclo[2.2.1]heptane-2-thiol | 211948-34-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4S)-1,3,3-Trimethyl-2-(6-methyl-pyridin-2-ylmethyl)-bicyclo[2.2.1]heptane-2-thiol
• 英文别名: (1R,2R,4S)-1,3,3-trimethyl-2-[(6-methylpyridin-2-yl)methyl]bicyclo[2.2.1]heptane-2-thiol
• CAS: 211948-34-4
• 化学式: C₁₇H₂₅NS
• 分子量: 275.458
• InChiKey: RGQXWPKFQICCCS-XKQJLSEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  13.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S)-1,3,3-Trimethyl-2-(6-methyl-pyridin-2-ylmethyl)-bicyclo[2.2.1]heptane-2-thiol 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2,6-Bis-((1R,2R,4S)-2-benzylsulfanyl-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-ylmethyl)-pyridine
  参考文献：
  名称：

  Chiral Nonracemic Pyridine Thiols and Thioethers Applied in Palladium-Catalyzed Allylic Substitution. An Example of Near-Perfect Enantioselection

  摘要：

  Pyridine thiols and dithiols have been synthesized by base-induced addition of 2,6-lutidine to thiofenchone. These thiols were converted to their thioether derivatives by alkylation. Application of these compounds in palladium-catalyzed allylic substitution on 1,3-diphenylprop-2-enyl acetate gave nearly absolute enantiomeric excess (98%) and high chemical yield (96%). Isolation of a palladium allylic intermediate gave insight in the origin of chiral recognition for these systems.

  DOI：

  10.1021/jo9806299
• 作为产物：
  描述：

  2,6-二甲基吡啶 、 thiofenchone 在 正丁基锂 作用下， 生成 (1R,2R,4S)-1,3,3-Trimethyl-2-(6-methyl-pyridin-2-ylmethyl)-bicyclo[2.2.1]heptane-2-thiol
  参考文献：
  名称：

  Chiral Nonracemic Pyridine Thiols and Thioethers Applied in Palladium-Catalyzed Allylic Substitution. An Example of Near-Perfect Enantioselection

  摘要：

  Pyridine thiols and dithiols have been synthesized by base-induced addition of 2,6-lutidine to thiofenchone. These thiols were converted to their thioether derivatives by alkylation. Application of these compounds in palladium-catalyzed allylic substitution on 1,3-diphenylprop-2-enyl acetate gave nearly absolute enantiomeric excess (98%) and high chemical yield (96%). Isolation of a palladium allylic intermediate gave insight in the origin of chiral recognition for these systems.

  DOI：

  10.1021/jo9806299

文献信息

• New pyridine dithiols: synthesis and structures of complexes with acids
  作者：Bartjan Koning、Ron Hulst、Arjan Bouter、Jan Buter、Auke Meetsma、Richard M. Kellogg

  DOI：10.1039/a701774j

  日期：——

  Pyridine dithiols have been synthesized by base-induced addition of 2,6-lutidine to (non-enolisable) thioketones, and have been found to encapsulate various acids.

  已通过碱诱导将2,6-呋喃啶添加到（不可酮化的）硫酮中合成了吡啶二硫醇，并发现其能够封装多种酸。
• Chiral Nonracemic Pyridine Thiols and Thioethers Applied in Palladium-Catalyzed Allylic Substitution. An Example of Near-Perfect Enantioselection
  作者：B. Koning、A. Meetsma、R. M. Kellogg

  DOI：10.1021/jo9806299

  日期：1998.8.1

  Pyridine thiols and dithiols have been synthesized by base-induced addition of 2,6-lutidine to thiofenchone. These thiols were converted to their thioether derivatives by alkylation. Application of these compounds in palladium-catalyzed allylic substitution on 1,3-diphenylprop-2-enyl acetate gave nearly absolute enantiomeric excess (98%) and high chemical yield (96%). Isolation of a palladium allylic intermediate gave insight in the origin of chiral recognition for these systems.