hexacyclo<29.4.0.0^3,8.0^10,15.0^17,22.0^24,29>pentatriconta-1(31),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-pentadecaene-2,16-dione | 142066-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexacyclo<29.4.0.0^3,8.0^10,15.0^17,22.0^24,29>pentatriconta-1(31),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-pentadecaene-2,16-dione
• 英文别名: <1₅>Orthocyclophane-1,3-dione；hexacyclo[29.4.0.0^3,8.0^10,15.0^17,22.0^24,29]pentatriconta-1(31),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-pentadecaene-2,16-dione；hexacyclo[29.4.0.03,8.010,15.017,22.024,29]pentatriaconta-1(35),3,5,7,10,12,14,17,19,21,24,26,28,31,33-pentadecaene-2,16-dione
• CAS: 142066-48-6
• 化学式: C₃₅H₂₆O₂
• 分子量: 478.59
• InChiKey: KEXYWFXDPFHKMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  37.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  hexacyclo<29.4.0.0^3,8.0^10,15.0^17,22.0^24,29>pentatriconta-1(31),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-pentadecaene-2,16-dione 在 ammonium cerium(IV) nitrate 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以66%的产率得到<1₅>Ketonand
  参考文献：
  名称：

  Orthocyclophanes. 3. Ketonands, Novel Ketonic Crowns of Polyoxo[1n]orthocyclophane Constitution

  摘要：

  Synthetic studies of a new family of novel ketonic macrocycles are reported. Exhaustive oxidation of all of the methylenes in odd-numbered [1(n)]orthocyclophanes ([1(n)]OCPs) resulted in the polyoxo derivatives of a cyclopolyorthobenzoyl or polyoxo[1(n)]orthocyclophane constitution. This new class of ketonic crowns is referred to as [1(n)]orthocyclophanepolyones and includes [1(5)] orthocyclophane-pentaone, [1(7)]orthocyclophaneheptaone, and [1(9)]orthocyclophanenonaone. We suggest the generic name ''ketonands'' for these ketonic crowns. Structures of ketonands were confirmed by spectral and X-ray crystallographic analyses.

  DOI：

  10.1021/jo00083a033
• 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， 生成 hexacyclo<29.4.0.0^3,8.0^10,15.0^17,22.0^24,29>pentatriconta-1(31),3(8),4,6,10(15),11,13,17(22),18,20,24(29),25,27,32,34-pentadecaene-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

• Lee Woo Young, Park Chang Hee, Kim Hyo-Joong, Kim Sangsoo, J. Org. Chem, 59 (1994) N 4, S 878-884
  作者：Lee Woo Young, Park Chang Hee, Kim Hyo-Joong, Kim Sangsoo

  DOI：——

  日期：——
• 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.
• Orthocyclophanes. 3. Ketonands, Novel Ketonic Crowns of Polyoxo[1n]orthocyclophane Constitution
  作者：Woo Young Lee、Chang Hee Park、Hyo-Joong Kim、Sangsoo Kim

  DOI：10.1021/jo00083a033

  日期：1994.2

  Synthetic studies of a new family of novel ketonic macrocycles are reported. Exhaustive oxidation of all of the methylenes in odd-numbered [1(n)]orthocyclophanes ([1(n)]OCPs) resulted in the polyoxo derivatives of a cyclopolyorthobenzoyl or polyoxo[1(n)]orthocyclophane constitution. This new class of ketonic crowns is referred to as [1(n)]orthocyclophanepolyones and includes [1(5)] orthocyclophane-pentaone, [1(7)]orthocyclophaneheptaone, and [1(9)]orthocyclophanenonaone. We suggest the generic name ''ketonands'' for these ketonic crowns. Structures of ketonands were confirmed by spectral and X-ray crystallographic analyses.