4-bromo-3-penyl-2-benzofuran-1(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-bromo-3-penyl-2-benzofuran-1(3H)-one
• 英文别名: 4-bromo-3-phenyl-phthalide；4-Brom-3-phenyl-phthalid；4-bromo-3-phenyl-3H-2-benzofuran-1-one
• 化学式: C₁₄H₉BrO₂
• 分子量: 289.128
• InChiKey: OIOAQFQMRDBAQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间溴苯甲酸 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-bromo-3-penyl-2-benzofuran-1(3H)-one
  参考文献：
  名称：

  ortho-Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides

  摘要：

  Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 degreesC, lithium 3-chloroibromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chlorolbromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the corresponding 3-chloro derivative and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base.

  DOI：

  10.1021/jo026514t

文献信息

• Bergmann; Loewenthal, Bulletin de la Societe Chimique de France, 1952, p. 66,71
  作者：Bergmann、Loewenthal

  DOI：——

  日期：——
• <i>ortho-</i>Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides
  作者：Frédéric Gohier、Jacques Mortier

  DOI：10.1021/jo026514t

  日期：2003.3.1

  Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 degreesC, lithium 3-chloroibromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chlorolbromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the corresponding 3-chloro derivative and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base.