heptacyclo<29.4.0.0^2,16.0^3,8.0^10,15.0^17,22.0^24,29>pentatriaconta-1(31),2(16),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-hexadecaen-9-one | 142066-50-0

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: heptacyclo<29.4.0.0^2,16.0^3,8.0^10,15.0^17,22.0^24,29>pentatriaconta-1(31),2(16),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-hexadecaen-9-one
• 英文别名: heptacyclo[29.4.0.0^2,16.0^3,8.0^10,15.0^17,22.0^24,29]pentatriaconta-1(31),2(16),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-hexadecaen-9-one；heptacyclo[20.13.0.02,7.09,14.016,21.023,28.030,35]pentatriaconta-1(22),2,4,6,9,11,13,16,18,20,23,25,27,30,32,34-hexadecaen-29-one
• CAS: 142066-50-0
• 化学式: C₃₅H₂₄O
• 分子量: 460.575
• InChiKey: ZALUUKPJEZPRFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  36.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  bis(2-bromophenyl)methane 在 lithium aluminium tetrahydride 、 正丁基锂 、 titanium(III) chloride 、 Celite 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 64.0h， 生成 heptacyclo<29.4.0.0^2,16.0^3,8.0^10,15.0^17,22.0^24,29>pentatriaconta-1(31),2(16),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-hexadecaen-9-one
  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