1-(三异丙基硅烷基)-1H-吡咯并[2,3-B]吡啶 | 1093759-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 1-(三异丙基硅烷基)-1H-吡咯并[2,3-B]吡啶
• 中文别名: 1-(三异丙基硅烷基)-1H-吡咯并[2,3-b]吡啶
• 英文名称: 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 1-[Tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine；tri(propan-2-yl)-pyrrolo[2,3-b]pyridin-1-ylsilane
• CAS: 1093759-49-9
• 化学式: C₁₆H₂₆N₂Si
• 分子量: 274.481
• InChiKey: DDESQHZPBHAOPS-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±24.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-(三异丙基硅烷基)-1H-吡咯并[2,3-B]吡啶 、 五氟苯 在 三苯基膦氯金 、 1-pivaloyloxy-1,2-benziodoxol-3(1H)-one 、 特戊酸银 、 二甲基亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以36%的产率得到3-(perfluorophenyl)-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridine
  参考文献：
  名称：

  Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation

  摘要：

  The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds: The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.

  DOI：

  10.1021/jacs.5b10593
• 作为产物：
  描述：

  1-三异丙基硅基-5-溴-7-氮杂吲哚 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到1-(三异丙基硅烷基)-1H-吡咯并[2,3-B]吡啶
  参考文献：
  名称：

  A Closer Look at the Bromine–Lithium Exchange with tert-Butyllithium in an Aryl Sulfonamide Synthesis

  摘要：

  A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, Is described. A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction Is determined for each aryl bromide in a GC-MS-assisted experiment.

  DOI：

  10.1021/ol4010454

文献信息

• [EN] AZAINDOLES USEFUL AS INHIBITORS OF ROCK AND OTHER PROTEIN KINASES<br/>[FR] AZAINDOLES UTILES EN TANT QU'INHIBITEURS DE LA PROTEINE SERINE/THREONINE KINASE SUPERHELICE DE LA FAMILLE RHO (ROCK) ET D'AUTRES PROTEINES KINASES
  申请人：VERTEX PHARMA

  公开号：WO2005103050A3

  公开（公告）日：2006-10-05
• Au-Catalyzed Cross-Coupling of Arenes via Double C–H Activation
  作者：Xacobe C. Cambeiro、Nanna Ahlsten、Igor Larrosa

  DOI：10.1021/jacs.5b10593

  日期：2015.12.23

  The first methodology for Au(I/III)-catalyzed oxidative cross-coupling of arenes via double C-H activation has been developed. The reaction is fully selective for the cross-coupling between electron-rich hetero-/carbocyclic arenes and electron-poor arenes bearing relatively acidic C-H bonds: The inherently high cross-selectivity of the system obviates the need for directing groups or a large excess of one of the coupling partners.
• A Closer Look at the Bromine–Lithium Exchange with <i>tert</i>-Butyllithium in an Aryl Sulfonamide Synthesis
  作者：Christopher Waldmann、Otmar Schober、Günter Haufe、Klaus Kopka

  DOI：10.1021/ol4010454

  日期：2013.6.21

  A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, Is described. A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction Is determined for each aryl bromide in a GC-MS-assisted experiment.