methyl 6-chloro-3,3-dimethyl-4-tosyl-3,4-dihydrocyclopenta[b]indole-1-carboxylate | 1384896-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 6-chloro-3,3-dimethyl-4-tosyl-3,4-dihydrocyclopenta[b]indole-1-carboxylate
• 英文别名: Methyl 6-chloro-3,3-dimethyl-4-(4-methylphenyl)sulfonylcyclopenta[b]indole-1-carboxylate
• CAS: 1384896-41-6
• 化学式: C₂₂H₂₀ClNO₄S
• 分子量: 429.924
• InChiKey: LZEORXYLYPWAOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-chloro-3,3-dimethyl-4-tosyl-3,4-dihydrocyclopenta[b]indole-1-carboxylate 、 苯硼酸 在 potassium phosphate 、 dicyclohexyl(2,4,6-trimethoxyphenyl)phosphonium tetrafluoroborate 、 palladium diacetate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 53.23h， 以90%的产率得到methyl 3,3-dimethyl-6-phenyl-4-tosyl-3,4-dihydrocyclopenta[b]indole-1-carboxylate
  参考文献：
  名称：

  Electronic Effect Directed Au(I)-Catalyzed Cyclic C2–H Bond Functionalization of 3-Allenylindoles

  摘要：

  Gold-catalyzed cyclization reactions of indoles with an electron-deficient allene at the 3-position led to formation of dihydrocyclopenta[b]indole derivatives in moderate to excellent yields via C2-H bond functionalization of the indole unit. The presence of the electron-withdrawing alkoxycarbonyl, dialkoxyphosphono, or phenyl is crutial for this transformation. The potential synthetic dihydrocyclopenta[b]indole with the electron-withdrawing group has been demonstrated by applying a [3 + 2] cycloaddition reaction to construct the tretracycloskeleton.

  DOI：

  10.1021/ol301408g
• 作为产物：
  描述：

  在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 28.0h， 以83%的产率得到methyl 6-chloro-3,3-dimethyl-4-tosyl-3,4-dihydrocyclopenta[b]indole-1-carboxylate
  参考文献：
  名称：

  Electronic Effect Directed Au(I)-Catalyzed Cyclic C2–H Bond Functionalization of 3-Allenylindoles

  摘要：

  Gold-catalyzed cyclization reactions of indoles with an electron-deficient allene at the 3-position led to formation of dihydrocyclopenta[b]indole derivatives in moderate to excellent yields via C2-H bond functionalization of the indole unit. The presence of the electron-withdrawing alkoxycarbonyl, dialkoxyphosphono, or phenyl is crutial for this transformation. The potential synthetic dihydrocyclopenta[b]indole with the electron-withdrawing group has been demonstrated by applying a [3 + 2] cycloaddition reaction to construct the tretracycloskeleton.

  DOI：

  10.1021/ol301408g