hexacyclo<22.4.0.0^2,16.0^3,8.0^10,15.0^17,22>octacosa-1(24),2(16),3(8),4,6,10(15),11,13,17(22),18,20,25,27-tridecaene | 142066-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: hexacyclo<22.4.0.0^2,16.0^3,8.0^10,15.0^17,22>octacosa-1(24),2(16),3(8),4,6,10(15),11,13,17(22),18,20,25,27-tridecaene
• 英文别名: hexacyclo[22.4.0.0^2,16.0^3,8.0^10,15.0^17,22]octacosa-1(24),2(16),3(8),4,6,10(15),11,13,17(22),18,20,25,27-tridecaene；Hexacyclo[13.13.0.02,7.09,14.016,21.023,28]octacosa-1(15),2,4,6,9,11,13,16,18,20,23,25,27-tridecaene
• CAS: 142066-45-3
• 化学式: C₂₈H₂₀
• 分子量: 356.467
• InChiKey: RDHTXPQXPMNTFO-UHFFFAOYSA-N

物化性质

• 沸点：
  518.6±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  hexacyclo<22.4.0.0^2,16.0^3,8.0^10,15.0^17,22>octacosa-1(24),2(16),3(8),4,6,10(15),11,13,17(22),18,20,25,27-tridecaene 在 Celite 、 pyridinium chlorochromate 作用下， 以 苯 为溶剂， 反应 16.0h， 以77%的产率得到hexacyclo<22.4.0.0^2,16.0^3,8.0^10,15.0^17,22>octacosa-1(24),2(16),3(8),4,6,10(15),11,13,17(22),18,20,25,27-tridecaene-9,23-dione
  参考文献：
  名称：

  Orthocyclophanes. 1. Synthesis and characterization of [14]- and [15]orthocyclophanes and bicyclic biscyclophanes

  摘要：

  [1(4)]- and [1(5)]orthocyclophanes have been designed, synthesized and characterized. Dimetalation of bis(2-bromophenyl)methane (14) to the corresponding dilithio reagent 21, followed by reaction with aromatic dialdehydes bis(2-formylphenyl)methane (20) and 1,2-bis(2-formylbenzyl)benzene (27), gave cyclic diols 22 and 28, respectively. Oxidation of the diols with PCC to the corresponding cyclic diketones 23 and 29, followed by palladium-catalyzed reduction, afforded [1(4)]- and [1(5)]orthocyclophanes, 4 and 5. Bicyclic biscyclophanes were also prepared from the cyclic diketones giving rise to a new family of cyclophanes. Treatment of 23 and 29, respectively, with McMurry or Clemmensen reagents gave rise to intramolecular olefination to provide bicyclic biscyclophanes 24 and 30. Pd-catalyzed hydrogenation of 24 and 30 also gave 4 and 5. The benzylic positions of the cycloheptatriene moieties in 24 and 30 were very susceptible to oxidation to give ketones 26 and 32.

  DOI：

  10.1021/jo00041a007
• 作为产物：
  描述：

  bis(2-bromophenyl)methane 在 盐酸 、 正丁基锂 、 Celite 、 pyridinium chlorochromate 、 汞 、 锌 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 124.0h， 生成 hexacyclo<22.4.0.0^2,16.0^3,8.0^10,15.0^17,22>octacosa-1(24),2(16),3(8),4,6,10(15),11,13,17(22),18,20,25,27-tridecaene
  参考文献：
  名称：

  Orthocyclophanes. 1. Synthesis and characterization of [14]- and [15]orthocyclophanes and bicyclic biscyclophanes

  摘要：

  [1(4)]- and [1(5)]orthocyclophanes have been designed, synthesized and characterized. Dimetalation of bis(2-bromophenyl)methane (14) to the corresponding dilithio reagent 21, followed by reaction with aromatic dialdehydes bis(2-formylphenyl)methane (20) and 1,2-bis(2-formylbenzyl)benzene (27), gave cyclic diols 22 and 28, respectively. Oxidation of the diols with PCC to the corresponding cyclic diketones 23 and 29, followed by palladium-catalyzed reduction, afforded [1(4)]- and [1(5)]orthocyclophanes, 4 and 5. Bicyclic biscyclophanes were also prepared from the cyclic diketones giving rise to a new family of cyclophanes. Treatment of 23 and 29, respectively, with McMurry or Clemmensen reagents gave rise to intramolecular olefination to provide bicyclic biscyclophanes 24 and 30. Pd-catalyzed hydrogenation of 24 and 30 also gave 4 and 5. The benzylic positions of the cycloheptatriene moieties in 24 and 30 were very susceptible to oxidation to give ketones 26 and 32.

  DOI：

  10.1021/jo00041a007

文献信息

• Orthocyclophanes. 1. Synthesis and characterization of [14]- and [15]orthocyclophanes and bicyclic biscyclophanes
  作者：Woo Young Lee、Chang Hee Park、Young Dong Kim

  DOI：10.1021/jo00041a007

  日期：1992.7

  [1(4)]- and [1(5)]orthocyclophanes have been designed, synthesized and characterized. Dimetalation of bis(2-bromophenyl)methane (14) to the corresponding dilithio reagent 21, followed by reaction with aromatic dialdehydes bis(2-formylphenyl)methane (20) and 1,2-bis(2-formylbenzyl)benzene (27), gave cyclic diols 22 and 28, respectively. Oxidation of the diols with PCC to the corresponding cyclic diketones 23 and 29, followed by palladium-catalyzed reduction, afforded [1(4)]- and [1(5)]orthocyclophanes, 4 and 5. Bicyclic biscyclophanes were also prepared from the cyclic diketones giving rise to a new family of cyclophanes. Treatment of 23 and 29, respectively, with McMurry or Clemmensen reagents gave rise to intramolecular olefination to provide bicyclic biscyclophanes 24 and 30. Pd-catalyzed hydrogenation of 24 and 30 also gave 4 and 5. The benzylic positions of the cycloheptatriene moieties in 24 and 30 were very susceptible to oxidation to give ketones 26 and 32.