3-methyl-isochroman-1,4-dione | 14505-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-methyl-isochroman-1,4-dione
• 英文别名: 3-Methyl-isochroman-1,4-dion；3-Methylisochromene-1,4-dione；3-methylisochromene-1,4-dione
• CAS: 14505-49-8
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: GALWZNVZJCDSFX-UHFFFAOYSA-N

物化性质

• 沸点：
  371.6±31.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-isochroman-1,4-dione 在 甲醇 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (3RS,4RS)-4-hydroxy-3-methyl-isochroman-1-one 、 (3RS,4SR)-4-hydroxy-3-methyl-isochroman-1-one
  参考文献：
  名称：

  Oxidative Rearrangements of Isobenzofurans: Studies toward the Synthesis of the Ajudazols

  摘要：

  We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.

  DOI：

  10.1021/ol8009336
• 作为产物：
  描述：

  1-hydroxy-3-methyl-1H-isochromen-4-one 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以1.16 g的产率得到3-methyl-isochroman-1,4-dione
  参考文献：
  名称：

  Oxidative Rearrangements of Isobenzofurans: Studies toward the Synthesis of the Ajudazols

  摘要：

  We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.

  DOI：

  10.1021/ol8009336

文献信息

• (3+3)‐Annulation of Carbonyl Ylides with Donor–Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis
  作者：Martin Petzold、Peter G. Jones、Daniel B. Werz

  DOI：10.1002/anie.201814409

  日期：2019.5.6

  The first (3+3)‐annulation process of donor–acceptor cyclopropanes using synergistic catalysis is reported. The Rh2(OAc)4‐catalyzed decomposition of diazo carbonyl compounds generated carbonyl ylides in situ. These 1,3‐dipoles were converted with donor–acceptor cyclopropanes, activated by Lewis acid catalysis, to afford multiply substituted pyran scaffolds in high yield and diastereoselectivity. Extensive

  报道了使用协同催化的供体-受体环丙烷的第一个（3 + 3）环化过程。重氮羰基化合物的Rh 2（OAc）4催化分解原位生成羰基。这些1,3-偶极通过供体-受体环丙烷转化，并通过路易斯酸催化活化，从而以高收率和非对映选择性提供多取代的吡喃骨架。广泛的优化研究使人们能够利用溶剂对中间反应性的影响，获得9-氧杂双环[3.3.1]壬南-2-酮和10-氧杂双环[4.3.1]癸烯-2-醇核。
• Oxidative Rearrangements of Isobenzofurans: Studies toward the Synthesis of the Ajudazols
  作者：Stephen J. Hobson、Andrew Parkin、Rodolfo Marquez

  DOI：10.1021/ol8009336

  日期：2008.7.3

  We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.