7-bromo-2-chloro-3-(trimethylsilyl)furo[3,2-b]pyridine | 1436383-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 7-bromo-2-chloro-3-(trimethylsilyl)furo[3,2-b]pyridine
• 英文别名: (7-Bromo-2-chlorofuro[3,2-b]pyridin-3-yl)-trimethylsilane；(7-bromo-2-chlorofuro[3,2-b]pyridin-3-yl)-trimethylsilane
• CAS: 1436383-77-5
• 化学式: C₁₀H₁₁BrClNOSi
• 分子量: 304.646
• InChiKey: LQIZQWYYZZXSEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-bromo-2-chloro-3-(trimethylsilyl)furo[3,2-b]pyridine 、 2-chloro-7-(tri-n-butylstannyl)-3-(trimethylsilyl)furo[3,2-b]pyridine 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以65%的产率得到2,2’-bis-chloro-3,3′-bistrimethylsilyl-7,7′-bifuro[3,2-b]pyridine
  参考文献：
  名称：

  Successive Regioselective Metalations of Fused Heterocycles: Synthesis of Polyfunctionalized Furo[3,2-b]pyridines

  摘要：

  The furopyridine framework was chosen as a target for a lithiation study, in order to define the most effective conditions leading to the total functionalization of the heterocycle. Consequently, a detailed procedure for successive regioselective lithiations/electrophilic trapping of furo[3,2-b]pyridines is described and afforded several polyfunctionalized derivatives in good overall yields. A Pd-catalyzed cross-coupling reaction is also described and easily yielded the 7,7'-bifuro[3,2-b]pyridine.

  DOI：

  10.1021/jo400748n
• 作为产物：
  描述：

  2-chloro-3-(trimethylsilyl)furo[3,2-b]pyridine 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 四溴化碳 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以205 mg的产率得到7-bromo-2-chloro-3-(trimethylsilyl)furo[3,2-b]pyridine
  参考文献：
  名称：

  稠合杂环的一锅法多重锂化工艺

  摘要：

  已经开发出一种有效的一锅法，涉及两个或三个连续的区域选择性锂化/亲电捕获阶段，通过从 2-氯呋喃 [3,2-b] 吡啶开始，以良好的总产率提供几种多取代衍生物。

  DOI：

  10.1002/ejoc.201402967

文献信息

• One-Pot Multiple Lithiation Processes of Fused Heterocycles
  作者：Adeline Jasselin-Hinschberger、Corinne Comoy、Yves Fort

  DOI：10.1002/ejoc.201402967

  日期：2014.11

  An efficient one-pot process that involves two or three successive regioselective lithiation/electrophilic trapping stages has been developed that affords several polysubstituted derivatives in good overall yields by starting from 2-chlorofuro[3,2-b]pyridine.

  已经开发出一种有效的一锅法，涉及两个或三个连续的区域选择性锂化/亲电捕获阶段，通过从 2-氯呋喃 [3,2-b] 吡啶开始，以良好的总产率提供几种多取代衍生物。
• Successive Regioselective Metalations of Fused Heterocycles: Synthesis of Polyfunctionalized Furo[3,2-<i>b</i>]pyridines
  作者：Adeline Jasselin-Hinschberger、Corinne Comoy、Anthony Chartoire、Yves Fort

  DOI：10.1021/jo400748n

  日期：2013.6.7

  The furopyridine framework was chosen as a target for a lithiation study, in order to define the most effective conditions leading to the total functionalization of the heterocycle. Consequently, a detailed procedure for successive regioselective lithiations/electrophilic trapping of furo[3,2-b]pyridines is described and afforded several polyfunctionalized derivatives in good overall yields. A Pd-catalyzed cross-coupling reaction is also described and easily yielded the 7,7'-bifuro[3,2-b]pyridine.