10-oxa-2,3-benzo-syn-sesquinorbornene | 88230-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 10-oxa-2,3-benzo-syn-sesquinorbornene
• 英文别名: 10-oxabenzo-syn-sesquinorbornene；(1S,3R,6S,8R)-15-oxapentacyclo[6.6.1.13,6.02,7.09,14]hexadeca-2(7),9,11,13-tetraene
• CAS: 88230-07-3
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: MYSWSYIZGBJZFN-NWQDQBDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  10-oxa-2,3-benzo-syn-sesquinorbornene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到1,2,3,4,9,10-Hexahydro-4a,9a:9,10-exo,exo-diepoxy-1,4-exo-methanonaphthalene
  参考文献：
  名称：

  Thermal and photochemical reactions of syn-oxabenzosesquinorbornene (1,2,3,4,9,10-hexahydro-9,10-exo-epoxy-1,4-exo-methanoanthracene)

  摘要：

  DOI：

  10.1021/jo00178a009
• 作为产物：
  描述：

  4-oxatricyclo<5.2.1.0^2,6>deca-2,5-diene 、 邻氨基苯甲酸 在 亚硝酸异戊酯 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.25h， 以70%的产率得到10-oxa-2,3-benzo-syn-sesquinorbornene
  参考文献：
  名称：

  Thermal and photochemical reactions of syn-oxabenzosesquinorbornene (1,2,3,4,9,10-hexahydro-9,10-exo-epoxy-1,4-exo-methanoanthracene)

  摘要：

  DOI：

  10.1021/jo00178a009

文献信息

• syn- and anti-Sesquinorbornenes as mechanistic probes in reactions of the carbon-carbon double bond
  作者：Antonius A. M. Roof、William J. Winter、Paul D. Bartlett

  DOI：10.1021/jo00221a025

  日期：1985.10
• Sulfuration of the norbornene double bond
  作者：Paul D. Bartlett、Tirthankar Ghosh

  DOI：10.1021/jo00231a020

  日期：1987.10
• Spontaneous oxygenation of cyclic olefins. Effects of strain
  作者：Paul D. Bartlett、Rajiv Banavali

  DOI：10.1021/jo00021a016

  日期：1991.10

  Reactivity of strained olefins 1-3, 41, and 44 toward spontaneous oxygenation has been evaluated. Angle-strained olefins 1, 32, and 35 react spontaneously with ground-state triplet oxygen, at room temperature, to yield quantitatively, not copolymers or hydroperoxides, but epoxides and diketones in approximately a 2:1 ratio. The autoxidation of 1 is carried out with various solvents, inhibitors, initiators, and in the presence of 2 and 1,2-dimethylcyclohexene to determine the mechanistic details. Compared with 1, autoxidation of 2 and 3 follows a different route yielding mainly hydroperoxides along with other products. The mechanism of the spontaneous autoxidation is discussed in light of these results.
• Rearrangement of 10-oxabenzo--sesquinorbornene by light and by acids
  作者：Paul D. Bartlett、Tirthankar Ghosh

  DOI：10.1016/s0040-4039(00)98116-4

  日期：1985.1
• BARTLETT, PAUL D.;GHOSH, TIRTHANKAR, J. ORG. CHEM., 52,(1987) N 22, 4937-4943
  作者：BARTLETT, PAUL D.、GHOSH, TIRTHANKAR

  DOI：——

  日期：——