(3E)-3-[iodo(trimethylsilyl)methylene]-5,6-dimethoxy-2-(4-methoxybenzyl)isoindolin-1-one | 848061-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3E)-3-[iodo(trimethylsilyl)methylene]-5,6-dimethoxy-2-(4-methoxybenzyl)isoindolin-1-one
• 英文别名: (3E)-3-[iodo(trimethylsilyl)methylidene]-5,6-dimethoxy-2-[(4-methoxyphenyl)methyl]isoindol-1-one
• CAS: 848061-27-8
• 化学式: C₂₂H₂₆INO₄Si
• 分子量: 523.443
• InChiKey: BBTNVCAIHOGKQY-MRCUWXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E)-3-[iodo(trimethylsilyl)methylene]-5,6-dimethoxy-2-(4-methoxybenzyl)isoindolin-1-one 在 potassium fluoride 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-[1-Iodo-meth-(E)-ylidene]-5,6-dimethoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization

  摘要：

  A variety of substituted isoindolin-l-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICI, I-2, and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.

  DOI：

  10.1021/jo048007c
• 作为产物：
  描述：

  4,5-dimethoxy-2-iodobenzoyl chloride 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.5h， 生成 (3E)-3-[iodo(trimethylsilyl)methylene]-5,6-dimethoxy-2-(4-methoxybenzyl)isoindolin-1-one
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization

  摘要：

  A variety of substituted isoindolin-l-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICI, I-2, and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.

  DOI：

  10.1021/jo048007c