[5-甲氧基-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸 | 149108-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [5-甲氧基-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸
• 英文名称: 5-Methoxy-1-tosyl-3-indole boronic acid
• 英文别名: (5-methoxy-1-tosyl-1H-indol-3-yl)boronic acid；[5-methoxy-1-(4-methylphenyl)sulfonylindol-3-yl]boronic acid
• CAS: 149108-62-3
• 化学式: C₁₆H₁₆BNO₅S
• 分子量: 345.184
• InChiKey: HVTVYGVLSXIXDW-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 、 [5-甲氧基-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.0h， 以90%的产率得到5-Methoxy-1-(toluene-4-sulfonyl)-3-(4-trifluoromethyl-pyridin-2-yl)-1H-indole
  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
• 作为产物：
  描述：

  5-甲氧基-1-[(4-甲基苯基)磺酰基]-1H-吲哚 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 [5-甲氧基-1-(4-甲基苯基)磺酰基吲哚-3-基]硼酸
  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

文献信息

• Palladium catalyzed cross-coupling reaction between 3-indole boronic acids and tetrahydropyridine triflates
  作者：Qi Zheng、Youhua Yang、Arnold R. Martin

  DOI：10.1016/s0040-4039(00)77582-4

  日期：1993.4

  The palladium catalyzed cross-coupling reaction between 3-indole boronic acids and vinyl triflates is a good method to introduce vinyl groups into the indole 3-position. The regioselectivity of the enolization of N-substituted-3-piperidones is far greater than previously reported. N-tosyl-3-indole boronic acids can be easily synthesized via mercuration-boronation method.
• Zheng, Qi; Yang, Youhua; Martin, Arnold R., Heterocycles, 1994, vol. 37, # 3, p. 1761 - 1772
  作者：Zheng, Qi、Yang, Youhua、Martin, Arnold R.

  DOI：——

  日期：——
• Synthesis and antitumor evaluation of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines
  作者：Biao Jiang、Xen-Nan Xiong、Cai-Guang Yang

  DOI：10.1016/s0960-894x(00)00704-6

  日期：2001.2

  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.
• Synthesis of Novel Analogues of Marine Indole Alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and Bis(indolyl)-4-trifluoromethylpyridines as Potential Anticancer Agents
  作者：Wen-Nan Xiong、Cai-Guang Yang、Biao Jiang

  DOI：10.1016/s0968-0896(01)00070-0

  日期：2001.7

  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.