nigellicine | 98063-20-8

• 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: nigellicine
• 英文别名: 3-methyl-1-oxo-6,7,8,9-tetrahydropyridazino[1,2-a]indazole-11-carboxylic acid
• CAS: 98063-20-8
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: FEJTUHSIRAJLOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 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 、 三溴化硼 、 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 162.0h， 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

文献信息

• Total Synthesis of Nigellicine and Nigeglanine Hydrobromide
  作者：Eric L. Elliott、Simon M. Bushell、Marta Cavero、Brian Tolan、T. Ross Kelly

  DOI：10.1021/ol050769m

  日期：2005.6.1

  [GRAPHICS]The first syntheses of the pyridazinoindazolium alkaloids nigellicine and nigeglanine hydrobromide via a common intermediate are described. Ortho-lithiation/acylation and the direct amination of an isatin ring system are the key steps in the synthesis.
• 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.