(4-bromo-3-nitro)phenoxy-tert-butyl-dimethyl-silane

• 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: (4-bromo-3-nitro)phenoxy-tert-butyl-dimethyl-silane
• 英文别名: (4-Bromo-3-nitrophenoxy)(tert-butyl)dimethylsilane；(4-bromo-3-nitrophenoxy)-tert-butyl-dimethylsilane
• 化学式: C₁₂H₁₈BrNO₃Si
• 分子量: 332.269
• InChiKey: ZFTSKPMPXYGPPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-bromo-3-nitro)phenoxy-tert-butyl-dimethyl-silane 、 2-硝基苯胺 在 tris(dibenzylideneacetone)dipalladium (0) caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以70%的产率得到[4-(tert-butyl-dimethyl-silanyloxy)-2-nitro-phenyl]-(2'-nitrophenyl)-amine
  参考文献：
  名称：

  Efficient Methods for the Synthesis of 2-Hydroxyphenazine Based on the Pd-Catalyzed N-Arylation of Aryl Bromides

  摘要：

  [GRAPHICS]Substituted diphenylamines can be synthesized by Pd(0)-catalyzed N-arylation using o-nitroanilines and nitro-substituted aryl bromides for a substrate. Cyclization of the diphenylamines by various methods, including the intramolecular Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine. This phenazine is required to synthesize methanophenazine, a novel redoxactive cofactor isolated from methanogenic archaea.

  DOI：

  10.1021/ol050198y
• 作为产物：
  描述：

  4-溴-3-硝基苯酚 、 叔丁基二甲基氯硅烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以99%的产率得到(4-bromo-3-nitro)phenoxy-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Efficient Methods for the Synthesis of 2-Hydroxyphenazine Based on the Pd-Catalyzed N-Arylation of Aryl Bromides

  摘要：

  [GRAPHICS]Substituted diphenylamines can be synthesized by Pd(0)-catalyzed N-arylation using o-nitroanilines and nitro-substituted aryl bromides for a substrate. Cyclization of the diphenylamines by various methods, including the intramolecular Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine. This phenazine is required to synthesize methanophenazine, a novel redoxactive cofactor isolated from methanogenic archaea.

  DOI：

  10.1021/ol050198y

文献信息

• Efficient Methods for the Synthesis of 2-Hydroxyphenazine Based on the Pd-Catalyzed <i>N</i>-Arylation of Aryl Bromides
  作者：Mario Tietze、Alberto Iglesias、Elena Merisor、Jürgen Conrad、Iris Klaiber、Uwe Beifuss

  DOI：10.1021/ol050198y

  日期：2005.4.14

  [GRAPHICS]Substituted diphenylamines can be synthesized by Pd(0)-catalyzed N-arylation using o-nitroanilines and nitro-substituted aryl bromides for a substrate. Cyclization of the diphenylamines by various methods, including the intramolecular Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine. This phenazine is required to synthesize methanophenazine, a novel redoxactive cofactor isolated from methanogenic archaea.