2-(2-bromo-6-methoxy-4-methylphenyl)-2-(ethoxycarbonyloxy)acetonitrile | 934548-26-2

• 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: 2-(2-bromo-6-methoxy-4-methylphenyl)-2-(ethoxycarbonyloxy)acetonitrile
• 英文别名: [(2-Bromo-6-methoxy-4-methylphenyl)-cyanomethyl] ethyl carbonate
• CAS: 934548-26-2
• 化学式: C₁₃H₁₄BrNO₄
• 分子量: 328.162
• InChiKey: JEHDYYPFIPSESU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-6-methoxy-4-methylphenyl)-2-(ethoxycarbonyloxy)acetonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到ethyl (2-bromo-6-methoxy-4-methylphenyl)-2-oxoacetate
  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：

  氰化钾 、 氯甲酸乙酯 、 2-bromo-6-methoxy-4-methylbenzaldehyde 在 18-冠醚-6 、 苄基三甲基氯化铵 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 15.0h， 以98%的产率得到2-(2-bromo-6-methoxy-4-methylphenyl)-2-(ethoxycarbonyloxy)acetonitrile
  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.