4-氯-3-(三乙基硅烷基)吡啶 | 123506-94-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 4-氯-3-(三乙基硅烷基)吡啶
• 中文别名: 2-羰基-2-苯基乙基2-丙基戊酸酯
• 英文名称: 4-chloro-3-(triethylsilyl)pyridine
• 英文别名: (4-chloropyridin-3-yl)-triethylsilane
• CAS: 123506-94-5
• 化学式: C₁₁H₁₈ClNSi
• 分子量: 227.809
• InChiKey: GWNRVPLCUVNANO-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 0.5 Torr)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯-3-(三乙基硅烷基)吡啶 、 甲基氯化镁 、 四氢呋喃 生成 4-Chloro-2-methyl-5-triethylsilanyl-2H-pyridine-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  COMINS, DANIEL L.;MYOUNG, YOUNG CHAN, J. ORG. CHEM., 55,(1990) N, C. 292-298

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴-2-氯吡啶 在 正丁基锂 、 copper(II) sulfate 、 二异丙胺 、 肼 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 128.0h， 生成 4-氯-3-(三乙基硅烷基)吡啶
  参考文献：
  名称：

  Regiochemically Flexible Substitutions of Di-, Tri-, and Tetrahalopyridines:  The Trialkylsilyl Trick

  摘要：

  2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.

  DOI：

  10.1021/jo047962z

文献信息

• Rerouting Nucleophilic Substitution from the 4-Position to the 2- or 6-Position of 2,4-Dihalopyridines and 2,4,6-Trihalopyridines: The Solution to a Long-Standing Problem
  作者：Manfred Schlosser、Thierry Rausis、Carla Bobbio

  DOI：10.1021/ol047826g

  日期：2005.1.1

  2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetrafluoropyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, the halogen at the 6-(2-)position is displaced selectively. This synthetically valuable regiocontrol can also be realized with other halopyridines such as 2,4-dichloro- and 2,4,6-trichloropyridine.
• Synthesis and synthetic utility of 1-acyl-5-(trialkylsilyl)-1,2-dihydropyridines. A synthesis of (.+-.)-elaeokanine A
  作者：Daniel L. Comins、Young Chan Myoung

  DOI：10.1021/jo00288a049

  日期：1990.1
• COMINS, DANIEL L.;MYOUNG, YOUNG CHAN, J. ORG. CHEM., 55,(1990) N, C. 292-298
  作者：COMINS, DANIEL L.、MYOUNG, YOUNG CHAN

  DOI：——

  日期：——
• Regiochemically Flexible Substitutions of Di-, Tri-, and Tetrahalopyridines:  The Trialkylsilyl Trick
  作者：Manfred Schlosser、Carla Bobbio、Thierry Rausis

  DOI：10.1021/jo047962z

  日期：2005.4.1

  2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.