2-[2,6-Bis(trifluoromethylsulfonyloxy)pyridin-3-yl]ethyl trifluoromethanesulfonate | 910052-68-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-[2,6-Bis(trifluoromethylsulfonyloxy)pyridin-3-yl]ethyl trifluoromethanesulfonate
• CAS: 910052-68-5
• 化学式: C₁₀H₆F₉NO₉S₃
• 分子量: 551.343
• InChiKey: GPLBFNREJBVWEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-[2,6-Bis(trifluoromethylsulfonyloxy)pyridin-3-yl]ethyl trifluoromethanesulfonate 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
• 作为产物：
  描述：

  在 吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-[2,6-Bis(trifluoromethylsulfonyloxy)pyridin-3-yl]ethyl 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