2-(o-methoxyphenyl)-6-methyl-4H-3,1-benzoxazin-4-one | 35710-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(o-methoxyphenyl)-6-methyl-4H-3,1-benzoxazin-4-one
• 英文别名: 2-(2-Methoxyphenyl)-6-methyl-3,1-benzoxazin-4-one
• CAS: 35710-18-0
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: VITVAZMPQADZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 3-碘-4-甲基苯胺 、 甲氧基苯甲酰氯 在 palladium diacetate N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、2.07 MPa 条件下， 反应 24.0h， 以89%的产率得到2-(o-methoxyphenyl)-6-methyl-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  A Simple Synthesis of 2-Substituted-4H-3,1-benzoxazin-4-ones by Palladium-Catalyzed Cyclocarbonylation of o-Iodoanilines with Acid Chlorides

  摘要：

  One-pat reaction of o-iodoanilines with acid chlorides and carbon monoxide, in the presence of a palladium catalyst and diisopropylethylamine, regioselectively affords 2-substituted-4H-3,1-benzoxazin-4-ones in good to excellent yields. The reaction is believed to proceed via in situ amide formation from an o-iodoaniline and an acid chloride, followed by oxidative addition to Pd(0), CO insertion, and intramolecular cyclization to form the 2-substituted-4H-3,1-benzoxazin-4-one derivatives.

  DOI：

  10.1021/ol990258y

文献信息

• A Simple Synthesis of 2-Substituted-4<i>H</i>-3,1-benzoxazin-4-ones by Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Iodoanilines with Acid Chlorides
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/ol990258y

  日期：1999.11.1

  One-pat reaction of o-iodoanilines with acid chlorides and carbon monoxide, in the presence of a palladium catalyst and diisopropylethylamine, regioselectively affords 2-substituted-4H-3,1-benzoxazin-4-ones in good to excellent yields. The reaction is believed to proceed via in situ amide formation from an o-iodoaniline and an acid chloride, followed by oxidative addition to Pd(0), CO insertion, and intramolecular cyclization to form the 2-substituted-4H-3,1-benzoxazin-4-one derivatives.