ethyl 1-(4-bromobutyl)-4-methoxy-6-methylindazole-3-carboxylate | 934548-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: ethyl 1-(4-bromobutyl)-4-methoxy-6-methylindazole-3-carboxylate
• CAS: 934548-31-9
• 化学式: C₁₆H₂₁BrN₂O₃
• 分子量: 369.258
• InChiKey: GMOUIQWINYDMQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-bromobutyl)-4-methoxy-6-methylindazole-3-carboxylate 在 三溴化硼 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 nigellicine
  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
• 作为产物：
  描述：

  2-(2-bromo-6-methoxy-4-methylphenyl)-2-(ethoxycarbonyloxy)acetonitrile 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 四丁基氟化铵 、 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 114.0h， 生成 ethyl 1-(4-bromobutyl)-4-methoxy-6-methylindazole-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.