2-(4,4-Dimethylpent-2-ynylsulfanyl)pyridine | 1000854-40-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4,4-Dimethylpent-2-ynylsulfanyl)pyridine
• CAS: 1000854-40-9
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: KQPVUYFTAXQUKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4,4-Dimethylpent-2-ynylsulfanyl)pyridine 在 正丁基锂 、 溶剂黄146 作用下， 以 正己烷 、 乙醚 为溶剂， 反应 2.0h， 生成 (aS)-4,4-dimethyl-penta-1,2-dienyl 2-pyridinyl sulfide 、 (aR)-4,4-dimethyl-penta-1,2-dienyl 2-pyridinyl sulfide
  参考文献：
  名称：

  Asymmetric lithiation of 2-alkynyl aryl sulfides—Enantio- and diastereoselective formation of allenyl aryl sulfides and their application in nickel-catalyzed cross-coupling reactions

  摘要：

  The enantio-and diastereoselective synthesis of allenyl aryl sulfides by asymmetric lithiation of 2-alkynyl(2-hetero)aryl sulfides is described. A dynamic thermodynamic resolution by selective crystallization of the intermediate lithium complexes derived from deprotonation, applying a bis(oxazoline) ligand, was achieved to give enantioselectivities up to 85% ee. Subsequent stereospecific nickel-catalyzed cross-coupling reactions with arylzinc reagents established a versatile access to threefold carbon-substituted allenes. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.037

文献信息

• Asymmetric lithiation of 2-alkynyl aryl sulfides—Enantio- and diastereoselective formation of allenyl aryl sulfides and their application in nickel-catalyzed cross-coupling reactions
  作者：Ralf Otte、Birgit Wibbeling、Roland Fröhlich、Shuichi Nakamura、Norio Shibata、Takeshi Toru、Dieter Hoppe

  DOI：10.1016/j.tetlet.2007.10.037

  日期：2007.12

  The enantio-and diastereoselective synthesis of allenyl aryl sulfides by asymmetric lithiation of 2-alkynyl(2-hetero)aryl sulfides is described. A dynamic thermodynamic resolution by selective crystallization of the intermediate lithium complexes derived from deprotonation, applying a bis(oxazoline) ligand, was achieved to give enantioselectivities up to 85% ee. Subsequent stereospecific nickel-catalyzed cross-coupling reactions with arylzinc reagents established a versatile access to threefold carbon-substituted allenes. (C) 2007 Elsevier Ltd. All rights reserved.