(1-Benzylpyrrolo[2,3-b]pyridin-6-yl) trifluoromethanesulfonate | 910052-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (1-Benzylpyrrolo[2,3-b]pyridin-6-yl) trifluoromethanesulfonate
• CAS: 910052-75-4
• 化学式: C₁₅H₁₁F₃N₂O₃S
• 分子量: 356.325
• InChiKey: SJWXCCXSRHPLTR-UHFFFAOYSA-N

物化性质

• 熔点：
  40.5-41 °C
• 沸点：
  483.2±45.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1-Benzylpyrrolo[2,3-b]pyridin-6-yl) trifluoromethanesulfonate 、 四甲基锡 在 bis-triphenylphosphine-palladium(II) chloride 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以81%的产率得到1-Benzyl-6-methylpyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Synthesis and Cross-Coupling Reactions of 7-Azaindoles via a New Donor−Acceptor Cyclopropane

  摘要：

  A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane- 1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.

  DOI：

  10.1021/ol061379i
• 作为产物：
  描述：

  5-Azaspiro[2.5]oct-7-ene-4,6-dione 在 manganese(IV) oxide 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成 (1-Benzylpyrrolo[2,3-b]pyridin-6-yl) trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and Cross-Coupling Reactions of 7-Azaindoles via a New Donor−Acceptor Cyclopropane

  摘要：

  A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane- 1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.

  DOI：

  10.1021/ol061379i

文献信息

• Synthesis and Cross-Coupling Reactions of 7-Azaindoles via a New Donor−Acceptor Cyclopropane
  作者：Xiaomei Zheng、Michael A. Kerr

  DOI：10.1021/ol061379i

  日期：2006.8.1

  A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane- 1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.