2-(5-(dimethylamino)-2-nitrosophenoxy)-1-phenylethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-(dimethylamino)-2-nitrosophenoxy)-1-phenylethanone
• 英文别名: 2-[5-(Dimethylamino)-2-nitrosophenoxy]-1-phenylethanone；2-[5-(dimethylamino)-2-nitrosophenoxy]-1-phenylethanone
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: NJVIIMJAZTXIRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5-(dimethylamino)-2-nitrosophenoxy)-1-phenylethanone 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以67%的产率得到2-benzoyl-6-(dimethylamino)benzoxazole
  参考文献：
  名称：

  Base-Promoted Domino Reaction of 5-Substituted 2-Nitrosophenols with Bromomethyl Aryl Ketones: A Transition-Metal-Free Approach to 2-Aroylbenzoxazoles

  摘要：

  The reaction of 5-substituted 2-nitrosophenols with bromomethyl aryl ketones and related compounds employing K2CO3 as a base in refluxing THF and DMF at 80 degrees C, respectively, delivers 2-aroylbenzoxazoles in a single step with yields up to 85%. The new method involves an intermolecular nucleophilic substitution followed by intramolecular 1,2-addition practical access to 2-aroylbenzoxazoles under transition-metal-free conditions.

  DOI：

  10.1021/acs.joc.5b02000
• 作为产物：
  描述：

  3-羟基-N,N-二甲基苯胺 在 盐酸 、 水 、 potassium carbonate 、 sodium nitrite 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 2-(5-(dimethylamino)-2-nitrosophenoxy)-1-phenylethanone
  参考文献：
  名称：

  Base-Promoted Domino Reaction of 5-Substituted 2-Nitrosophenols with Bromomethyl Aryl Ketones: A Transition-Metal-Free Approach to 2-Aroylbenzoxazoles

  摘要：

  The reaction of 5-substituted 2-nitrosophenols with bromomethyl aryl ketones and related compounds employing K2CO3 as a base in refluxing THF and DMF at 80 degrees C, respectively, delivers 2-aroylbenzoxazoles in a single step with yields up to 85%. The new method involves an intermolecular nucleophilic substitution followed by intramolecular 1,2-addition practical access to 2-aroylbenzoxazoles under transition-metal-free conditions.

  DOI：

  10.1021/acs.joc.5b02000

文献信息

• Base-Promoted Domino Reaction of 5-Substituted 2-Nitrosophenols with Bromomethyl Aryl Ketones: A Transition-Metal-Free Approach to 2-Aroylbenzoxazoles
  作者：Nayyef Aljaar、Chandi C. Malakar、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/acs.joc.5b02000

  日期：2015.11.6

  The reaction of 5-substituted 2-nitrosophenols with bromomethyl aryl ketones and related compounds employing K2CO3 as a base in refluxing THF and DMF at 80 degrees C, respectively, delivers 2-aroylbenzoxazoles in a single step with yields up to 85%. The new method involves an intermolecular nucleophilic substitution followed by intramolecular 1,2-addition practical access to 2-aroylbenzoxazoles under transition-metal-free conditions.