pentacyclo<22.4.0.0^3,8.0^10,15.0^17,22>octacosa-1(24),3(8), 4,6,10(15),11,13,17(22),18,20,25,27-dodecaene-2,16-dione | 142066-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pentacyclo<22.4.0.0^3,8.0^10,15.0^17,22>octacosa-1(24),3(8), 4,6,10(15),11,13,17(22),18,20,25,27-dodecaene-2,16-dione
• 英文别名: pentacyclo[22.4.0.0^3,8.0^10,15.0^17,22]octacosa-1(24),3(8), 4,6,10(15),11,13,17(22),18,20,25,27-dodecaene-2,16-dione；pentacyclo[22.4.0.03,8.010,15.017,22]octacosa-1(28),3,5,7,10,12,14,17,19,21,24,26-dodecaene-2,16-dione
• CAS: 142066-44-2
• 化学式: C₂₈H₂₀O₂
• 分子量: 388.466
• InChiKey: SKXFHLRDXMMMOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  30.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  pentacyclo<22.4.0.0^3,8.0^10,15.0^17,22>octacosa-1(24),3(8), 4,6,10(15),11,13,17(22),18,20,25,27-dodecaene-2,16-dione 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以80%的产率得到pentacyclo<22.4.0.0^3,8.0^10,15.0^17,22>octacosa-1(24),3(8), 4,6,10(15),11,13,17(22),18,20,25,27-dodecaene
  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 正丁基锂 、 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 pentacyclo<22.4.0.0^3,8.0^10,15.0^17,22>octacosa-1(24),3(8), 4,6,10(15),11,13,17(22),18,20,25,27-dodecaene-2,16-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

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.