3-(2-benzoylphenyl)-4-bromosydnone

• 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: 3-(2-benzoylphenyl)-4-bromosydnone
• 英文别名: 3-(2-Benzoylphenyl)-4-bromooxadiazol-3-ium-5-olate
• 化学式: C₁₅H₉BrN₂O₃
• 分子量: 345.152
• InChiKey: KEFWSERNZJMPKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-benzoylphenyl)-4-bromosydnone 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到3-Phenyl-indazole-1-carbonyl bromide
  参考文献：
  名称：

  Formation of 1-bromocarbonylindazoles via cleavage of 4-bromo ortho-substituted arylsydnones with HBr

  摘要：

  Treatment of 4-bromo-3-arylsydnones containing an ortho-carbonyl substituent (cf. 1d-j) with HBr gas leads to the corresponding, novel 1-bromocarbonyl-3-substituted indazoles (2d-k), generally in excellent yield.

  DOI：

  10.1016/s0040-4039(00)60556-7
• 作为产物：
  描述：

  N-甲基-N-甲基苯甲酰胺 、 3-苯雪梨酮 在 正丁基锂 、 四甲基乙二胺 、 溴 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以84%的产率得到3-(2-benzoylphenyl)-4-bromosydnone
  参考文献：
  名称：

  Sydnone Ring as an ortho-Director of Lithiation, 3: One-Pot Regiospecific o-Acylation and Subsequent Sydnone 4-Substitution

  摘要：

  Readily available 3-phenylsydnone (1) reacts with n-butyllithium/N,N,N',N'-tetramethylethylenediamine (TMEDA) to form the dilithio species 2, which can be acylated regiospecifically at the ortho-aryl position using N-methoxy-N-methylamides (Weinreb's amides) followed by reaction with a second, more reactive electrophile at the sydnone C-4 position. Asymmetrically substituted arylsydnones 7 are obtained in 57-86% yield.

  DOI：

  10.1080/00397910802664251

文献信息

• Sydnone Ring as an <i>ortho</i>-Director of Lithiation, 3: One-Pot Regiospecific <i>o</i>-Acylation and Subsequent Sydnone 4-Substitution
  作者：Kenneth Turnbull、Douglas M. Krein

  DOI：10.1080/00397910802664251

  日期：2009.7.21

  Readily available 3-phenylsydnone (1) reacts with n-butyllithium/N,N,N',N'-tetramethylethylenediamine (TMEDA) to form the dilithio species 2, which can be acylated regiospecifically at the ortho-aryl position using N-methoxy-N-methylamides (Weinreb's amides) followed by reaction with a second, more reactive electrophile at the sydnone C-4 position. Asymmetrically substituted arylsydnones 7 are obtained in 57-86% yield.
• Formation of 1-bromocarbonylindazoles via cleavage of 4-bromo ortho-substituted arylsydnones with HBr
  作者：Jeffrey A. Marx、Kenneth Turnbull

  DOI：10.1016/s0040-4039(00)60556-7

  日期：1993.1

  Treatment of 4-bromo-3-arylsydnones containing an ortho-carbonyl substituent (cf. 1d-j) with HBr gas leads to the corresponding, novel 1-bromocarbonyl-3-substituted indazoles (2d-k), generally in excellent yield.