tert-butyl-1-(4-methylphenylsulfonyl)indazole-3-carboxylate | 767288-60-8

• 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: tert-butyl-1-(4-methylphenylsulfonyl)indazole-3-carboxylate
• 英文别名: 3-tert-butoxycarbonyl-N-tosylindazole；Tert-butyl 1-(4-methylphenyl)sulfonylindazole-3-carboxylate
• CAS: 767288-60-8
• 化学式: C₁₉H₂₀N₂O₄S
• 分子量: 372.445
• InChiKey: NIJAVKZCQZTLFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  86.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-1-(4-methylphenylsulfonyl)indazole-3-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到3-t-butoxycarbonylindazol
  参考文献：
  名称：

  Efficient Synthesis of 3-Substituted Indazoles Using Pd-Catalyzed Intramolecular Amination Reaction ofN-Tosylhydrazones

  摘要：

  利用钯催化的2-溴苯腙衍生物的分子内胺化反应开发了制备3-取代吲唑的有效方法。在温和的反应条件下观察到良好的官能团相容性，并以中等至优异的收率获得了各种3-取代吲唑。

  DOI：

  10.1246/cl.2004.1026
• 作为产物：
  描述：

  2'-溴苯乙酮 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 4-二甲氨基吡啶 、 selenium(IV) oxide 、 碳酸二异丙酯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 tert-butyl-1-(4-methylphenylsulfonyl)indazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine

  摘要：

  Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.010

文献信息

• Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine
  作者：Kiyofumi Inamoto、Mika Katsuno、Takashi Yoshino、Yukari Arai、Kou Hiroya、Takao Sakamoto

  DOI：10.1016/j.tet.2007.01.010

  日期：2007.3

  Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described. (c) 2007 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of 3-Substituted Indazoles Using Pd-Catalyzed Intramolecular Amination Reaction of<i>N</i>-Tosylhydrazones
  作者：Kiyofumi Inamoto、Mika Katsuno、Takashi Yoshino、Ikue Suzuki、Kou Hiroya、Takao Sakamoto

  DOI：10.1246/cl.2004.1026

  日期：2004.8

  The efficient method for the preparation of 3-substituted indazoles was developed using the palladium catalyzed intramolecular amination reaction of 2-bromophenyl hydrazone derivatives. Good functional group compatibility was observed under mild reaction conditions and various 3-substituted indazoles were obtained in moderate to excellent yield.

  利用钯催化的2-溴苯腙衍生物的分子内胺化反应开发了制备3-取代吲唑的有效方法。在温和的反应条件下观察到良好的官能团相容性，并以中等至优异的收率获得了各种3-取代吲唑。