5,8-dimethoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-4,9-ethenobenzo[f]isoindole-1,3(2H)-dione | 1421331-93-2

• 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: 5,8-dimethoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-4,9-ethenobenzo[f]isoindole-1,3(2H)-dione
• 英文别名: (1S,8R,9R,13S)-3,6-dimethoxy-11-methyl-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,14-tetraene-10,12-dione
• CAS: 1421331-93-2
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: WHTRYIDZVOMZMW-XRQRDNCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TpW(NO)(PMe₃)(η²-5,8-dimethoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-4,9-ethenobenzo[f]isoindole-1,3(2H)-dione) 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.25h， 生成 5,8-dimethoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-4,9-ethenobenzo[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Exploiting the o-Quinodimethane Nature of Naphthalene: Cycloaddition Reactions with η²-Coordinated Tungsten–Naphthalene Complexes

  摘要：

  Naphthalene, when bound to the complex {TpW-(NO)(PMe3)}, is shown to be activated toward Diels-Alder cycloaddition in the bound ring with N-methylmaleimide (NMM). In its most stable form, the tungsten in this complex binds Cl and C2. However, the cyclization reaction is thought to proceed through an intermediate in which the metal binds C2 and C3, rendering the uncoordinated portion of the hydrocarbon similar to a quinodimethane. The reaction rates and regio- and stereo-chemistry are investigated for a series of substituted naphthalene ligands, and these observations support the proposed mechanism. An X-ray structure of the complex TpW(NO)(PMe3)(eta(2)-L), where L is the cycloadduct of NMM and 1,4-dimethylnaphthalene, confirms the endo stereochemistry of the cycloaddition.

  DOI：

  10.1021/om301238q