Trifluoro-methanesulfonic acid 1-(1-phenyl-ethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl ester | 910052-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Trifluoro-methanesulfonic acid 1-(1-phenyl-ethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl ester
• CAS: 910052-74-3
• 化学式: C₁₆H₁₅F₃N₂O₃S
• 分子量: 372.368
• InChiKey: WQCQZGKQVJIPPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.5
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 1-(1-phenyl-ethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl ester 在 manganese(IV) oxide 、 4 A molecular sieve 作用下， 以 苯 为溶剂， 反应 1.0h， 以91%的产率得到Trifluoro-methanesulfonic acid 1-(1-phenyl-ethyl)-1H-pyrrolo[2,3-b]pyridin-6-yl ester
  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 2.33h， 生成 Trifluoro-methanesulfonic acid 1-(1-phenyl-ethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-6-yl ester
  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