6,7-dimethoxy-3-(trimethylsilyl)isobenzofuran-1(3H)-one | 133932-07-7

• 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: 6,7-dimethoxy-3-(trimethylsilyl)isobenzofuran-1(3H)-one
• 英文别名: 3-(trimethylsilyl)-6,7-dimethoxyphthalide；6,7-dimethoxy-3-trimethylsilyl-3H-2-benzofuran-1-one
• CAS: 133932-07-7
• 化学式: C₁₃H₁₈O₄Si
• 分子量: 266.369
• InChiKey: GVGKUVIRIULPHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基-6-甲基-7,8-二氢[1,3]二氧杂环戊并[4,5-g]异喹啉-6-鎓碘化物 、 6,7-dimethoxy-3-(trimethylsilyl)isobenzofuran-1(3H)-one 在 potassium hydrogen difluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42%的产率得到noscapine
  参考文献：
  名称：

  A New Total Synthesis of (±)-α-Noscapine

  摘要：

  A new, convergent total synthesis of (+/-)-alpha-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.

  DOI：

  10.3987/com-13-12843
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 盐酸 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.0h， 生成 6,7-dimethoxy-3-(trimethylsilyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  A New Total Synthesis of (±)-α-Noscapine

  摘要：

  A new, convergent total synthesis of (+/-)-alpha-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.

  DOI：

  10.3987/com-13-12843

文献信息

• Fluoride ion promoted reactions of .alpha.-halo silanes: synthesis of stilbenes, epoxides, cyclopropanes, benzazepines, and phthalidylisoquinolines
  作者：Satinder V. Kessar、Paramjit Singh、Nachhattar Pal Kaur、Usha Chawla、Kalpana Shukla、Punam Aggarwal、D. Venugopal

  DOI：10.1021/jo00012a024

  日期：1991.6

  Reaction of alpha-halo silanes 1 with CsF in DMF affords stilbenes 5. In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed. A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.