25-Oxaoctacyclo[15.5.2.13,6.02,7.08,21.011,20.014,19.018,22]pentacosa-1(22),2(7),4,8(21),9,11(20),12,14(19),15,17,23-undecaene | 868708-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 25-Oxaoctacyclo[15.5.2.13,6.02,7.08,21.011,20.014,19.018,22]pentacosa-1(22),2(7),4,8(21),9,11(20),12,14(19),15,17,23-undecaene
• 英文别名: 25-oxaoctacyclo[15.5.2.13,6.02,7.08,21.011,20.014,19.018,22]pentacosa-1(22),2(7),4,8(21),9,11(20),12,14(19),15,17,23-undecaene
• CAS: 868708-03-6
• 化学式: C₂₄H₁₂O
• 分子量: 316.359
• InChiKey: XZROCHDLOZGANN-UHFFFAOYSA-N

物化性质

• 密度：
  1.577±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  25-Oxaoctacyclo[15.5.2.13,6.02,7.08,21.011,20.014,19.018,22]pentacosa-1(22),2(7),4,8(21),9,11(20),12,14(19),15,17,23-undecaene 在 2,6-bis-2-pyridyl-1,2,4,5-tetrazine 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以94%的产率得到isocorannulenofuran
  参考文献：
  名称：

  Isocorannulenofuran:  A Versatile Building Block for the Synthesis of Large Buckybowls

  摘要：

  Isocorannulenofuran, synthesized in two steps from accessible bromocorannulene, gives Diels-Alder adducts with benzynes which can be deoxygenated to produce large polycyclic aromatic hydrocarbons (PAHs) combining the bowl-shaped corannulene subunit with planar fragments.

  DOI：

  10.1021/ol0625839
• 作为产物：
  描述：

  呋喃 、 2-trimethylsilylcorannulenyl triflate 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以85%的产率得到25-Oxaoctacyclo[15.5.2.13,6.02,7.08,21.011,20.014,19.018,22]pentacosa-1(22),2(7),4,8(21),9,11(20),12,14(19),15,17,23-undecaene
  参考文献：
  名称：

  2-Trimethylsilylcorannulenyl Trifluoromethanesulfonate: An Efficient Precursor for 1,2-Didehydrocorannulene

  摘要：

  2-Trimethylsilylcorannulenyl trifluoromethanesulfonate, prepared from bromocorannulene, provides a means for generating of 1,2-didehydrocorannulene (corannulyne) under very mild conditions as demonstrated by the high-yield formation of its adducts with dienes.

  DOI：

  10.1021/ol801581z

文献信息

• The First Buckybowl Aryne. Corannulyne:  A Nonplanar Benzyne
  作者：Andrzej Sygula、Renata Sygula、Peter W. Rabideau

  DOI：10.1021/ol0519588

  日期：2005.10.1

  [GRAPHICS]Treatment of bromocorannulene with NaNH2/tBuOK in THF in the presence of furans or amines leads to formation of addition products in good yields, presumably through formation of 1,2-didehydrocorannulene (corannulyne). HUT calculations predict that corannulyne exists as a bowl-shaped entity and that the didehydrogenation energy of corannulene is slightly lower than that of benzene.
• 2-Trimethylsilylcorannulenyl Trifluoromethanesulfonate: An Efficient Precursor for 1,2-Didehydrocorannulene
  作者：Andrzej Sygula、Renata Sygula、Lesya Kobryn

  DOI：10.1021/ol801581z

  日期：2008.9.1

  2-Trimethylsilylcorannulenyl trifluoromethanesulfonate, prepared from bromocorannulene, provides a means for generating of 1,2-didehydrocorannulene (corannulyne) under very mild conditions as demonstrated by the high-yield formation of its adducts with dienes.
• Isocorannulenofuran:  A Versatile Building Block for the Synthesis of Large Buckybowls
  作者：Andrzej Sygula、Renata Sygula、Peter W. Rabideau

  DOI：10.1021/ol0625839

  日期：2006.12.1

  Isocorannulenofuran, synthesized in two steps from accessible bromocorannulene, gives Diels-Alder adducts with benzynes which can be deoxygenated to produce large polycyclic aromatic hydrocarbons (PAHs) combining the bowl-shaped corannulene subunit with planar fragments.