N-tosyl-6-methoxy-3-indolylboronic acid | 339540-15-7

• 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: N-tosyl-6-methoxy-3-indolylboronic acid
• 英文别名: [6-Methoxy-1-(4-methylphenyl)sulfonylindol-3-yl]boronic acid
• CAS: 339540-15-7
• 化学式: C₁₆H₁₆BNO₅S
• 分子量: 345.184
• InChiKey: QMITXLTZTHJWPR-UHFFFAOYSA-N

物化性质

• 沸点：
  607.1±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氯-4-三氟甲基吡啶 、 N-tosyl-6-methoxy-3-indolylboronic acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 以90%的产率得到4-trifluoromethyl-2-[3'-(N-toluenesulfonyl-6'-methoxyindolyl)]pyridine
  参考文献：
  名称：

  Synthesis and antitumor evaluation of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines

  摘要：

  A series of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines was designed and synthesized as potential antitumor agents. They were evaluated for preliminary cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxyl-indolyl)] pyridine was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00704-6
• 作为产物：
  描述：

  6-methoxy-1-tosyl-1H-indole 在 mercury(II) diacetate 、 二甲基硫 、 硼烷 、 水 作用下， 以 溶剂黄146 、 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-tosyl-6-methoxy-3-indolylboronic acid
  参考文献：
  名称：

  Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents

  摘要：

  Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethylpyridines were synthesized using Suzuki cross-coupling reaction between 2-chloro-4-trifluoromethylpyridine 9, 2,6-dichloro-4-trifluoromethylpyridine 6 or 2,6-dichloro-3-cyano-4-trifluoromethylpyridine 23 and N-tosyl-3-indolylboronic acid 10. They were evaluated for cytotoxic activity against P388 and A-549 cells with IC50 values. 4-Trifluoromethyl-2,6-bis[3'-(N-tosyl-6'-methoxylindolyl)]pyridine 18 was identified as the most potent in this series. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00070-0