7-oxanorbornadiene | 116215-71-5

• 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: 7-oxanorbornadiene
• 英文别名: 2,4,7-Trimethyl-4,7-dihydro-1H-4,7-epoxyisoindole-1,3(2H)-dione；2,4,7-trimethyl-4,7-epoxyisoindole-1,3-dione
• CAS: 116215-71-5
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: ZISXNNSYNDFHDN-UHFFFAOYSA-N

物化性质

• 沸点：
  330.7±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-二甲基呋喃 、 7-oxanorbornadiene 在 银 、 锌 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  The debromination route to norbornadienomaleimides and 7-oxanorbornadienomaleimides: Study of cycloaddition specificities with cyclic dienes.

  摘要：

  The debromination route (Zn/Ag in THF) which successfully produces 7-oxanorbornadienes fails in the norbornadiene series owing to different stereochemical positioning of the bromine substituents in the bicyclic precursors. A new oxygen, oxygen repulsive interaction is proposed to play a dominant but not exclusive role in determining stereochemical outcomes in the cycloaddition of 7-oxanorbornadienomaleimides with cyclopentadiene, furan and 2,5-dimethylfuran. The major product observed experimentally is in complete accord with that predicted by semi-empirical molecular orbital calculations (AM1).

  DOI：

  10.1016/0040-4039(95)01617-q
• 作为产物：
  描述：

  2,5-二甲基呋喃 在 银 、 锌 作用下， 以 四氢呋喃 为溶剂， 生成 7-oxanorbornadiene
  参考文献：
  名称：

  The debromination route to norbornadienomaleimides and 7-oxanorbornadienomaleimides: Study of cycloaddition specificities with cyclic dienes.

  摘要：

  The debromination route (Zn/Ag in THF) which successfully produces 7-oxanorbornadienes fails in the norbornadiene series owing to different stereochemical positioning of the bromine substituents in the bicyclic precursors. A new oxygen, oxygen repulsive interaction is proposed to play a dominant but not exclusive role in determining stereochemical outcomes in the cycloaddition of 7-oxanorbornadienomaleimides with cyclopentadiene, furan and 2,5-dimethylfuran. The major product observed experimentally is in complete accord with that predicted by semi-empirical molecular orbital calculations (AM1).

  DOI：

  10.1016/0040-4039(95)01617-q

文献信息

• Warrener, Ronald N.; Pitt, Ian G.; Russell, Richard A., Australian Journal of Chemistry, 1991, vol. 44, # 9, p. 1293 - 1305
  作者：Warrener, Ronald N.、Pitt, Ian G.、Russell, Richard A.

  DOI：——

  日期：——
• WARRENER, RONALD N.;PUSSELL, RICHARD A.;SOLOMON, ROBERT;PITT, IAN G.;BUTL+, TETRAHEDRON LETT., 28,(1987) N 51, 6503-6506
  作者：WARRENER, RONALD N.、PUSSELL, RICHARD A.、SOLOMON, ROBERT、PITT, IAN G.、BUTL+

  DOI：——

  日期：——
• The debromination route to norbornadienomaleimides and 7-oxanorbornadienomaleimides: Study of cycloaddition specificities with cyclic dienes.
  作者：Ronald N. Warrener、Gordon M. Elsey、Ljiljana Maksimovic、Martin R. Johnston、Colin H.L. Kennard

  DOI：10.1016/0040-4039(95)01617-q

  日期：1995.10

  The debromination route (Zn/Ag in THF) which successfully produces 7-oxanorbornadienes fails in the norbornadiene series owing to different stereochemical positioning of the bromine substituents in the bicyclic precursors. A new oxygen, oxygen repulsive interaction is proposed to play a dominant but not exclusive role in determining stereochemical outcomes in the cycloaddition of 7-oxanorbornadienomaleimides with cyclopentadiene, furan and 2,5-dimethylfuran. The major product observed experimentally is in complete accord with that predicted by semi-empirical molecular orbital calculations (AM1).