endo-4,9-epoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-benzisoindole-1,3(2H)-dione | 32427-42-2

• 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: endo-4,9-epoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-benzisoindole-1,3(2H)-dione
• 英文别名: (1R,8S,9R,13S)-11-methyl-14-oxa-11-azatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-10,12-dione
• CAS: 32427-42-2
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: LMUSZMPVOYVNRL-DTIDVZRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-dihydro-1,4-epoxy-3-phenylisoquinoline 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 endo-4,9-epoxy-2-methyl-3a,4,9,9a-tetrahydro-1H-benzisoindole-1,3(2H)-dione
  参考文献：
  名称：

  Benzyne-oxazole cycloadducts: isolation and retro-Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00290a025

文献信息

• Rigid Alicyclic Molecules from Bicyclo[2.2.1]hept-2-enes (=8,9,10-Trinorbornenes) and 1,4-Dipyridin-2-ylphthalazines as Stereoselective Coupling Agents
  作者：Davor Margetić、Yasujiro Murata、Koichi Komatsu、Željko Marinić

  DOI：10.1002/hlca.200800205

  日期：2009.2

  Abstractmagnified imageFor the preparation of rigid polycyclic molecules from 8,9,10‐trinorbornenes (=bicyclo[2.2.1]hept‐2‐enes), 1,4‐dipyridin‐2‐ylphthalazines were used. Cycloaddition reactions with trinorbornenes gave coupled products in a stereoselective manner. In these reactions, the phthalazines delivered a new bicyclo[2.2.2] moiety at the junction of two trinorbornene units, which could bear appropriate functional groups (Schemes 4and5). The crystal structure of a key cycloadduct,i.e., of18was also determined (Fig. 2). Relative reactivities for a series of phthalazines (Fig. 3) were estimated by density‐functional‐theory (DFT) calculations at the B3LYP/6‐31G* level (Table). The calculations indicated an increase of reactivity when the aromaticity of the phthalazine moiety is decreased. Finally, experimentally observed stereoselectivities of the phthalazine reactions with trinorbornenes were readily predicted by DFT calculations (Fig. 4).
• Substituent effects on rates of inter- and intramolecular cycloaddition reactions of isobenzofurans
  作者：David Tobia、Bruce Rickborn

  DOI：10.1021/jo00388a055

  日期：1987.6
• TOBIA D.; RICKBORN B., J. ORG. CHEM., 52,(1987) N 12, 2611-2615
  作者：TOBIA D.、 RICKBORN B.

  DOI：——

  日期：——