3-chloro-4-(2-(diphenylsilyl)ethyl)pyridine | 1430235-72-5

• 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: 3-chloro-4-(2-(diphenylsilyl)ethyl)pyridine
• CAS: 1430235-72-5
• 化学式: C₁₉H₁₈ClNSi
• 分子量: 323.897
• InChiKey: QQBBMEMYPWINOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(2-(diphenylsilyl)ethyl)pyridine 在 叔丁基过氧化氢 、 降冰片烯 、 N-碘代丁二酰亚胺 、 1,10-菲罗啉 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 四丁基氟化铵 、 silver fluoride 、 potassium hydride 作用下， 以 四氢呋喃 、 癸烷 、 乙腈 为溶剂， 反应 7.0h， 生成 2-(3-chloro-5-iodopyridin-4-yl)ethanol
  参考文献：
  名称：

  Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification

  摘要：

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.

  DOI：

  10.1021/ol400977r
• 作为产物：
  描述：

  4-乙烯基吡啶 在 降冰片烯 、 bis(1,5-cyclooctadiene)nickel (0) 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 1,10-菲罗啉 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 silver fluoride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 17.0h， 生成 3-chloro-4-(2-(diphenylsilyl)ethyl)pyridine
  参考文献：
  名称：

  Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification

  摘要：

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.

  DOI：

  10.1021/ol400977r