(1α,2β,5α,6β,9β,10α,13β,14α)-1,6,9,14-tetrachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadecane-7,8,15,16-tetraone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1α,2β,5α,6β,9β,10α,13β,14α)-1,6,9,14-tetrachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadecane-7,8,15,16-tetraone
• 英文别名: (1α,2α,5β,6β,9β,10β,13α,14α)-1,6,9,14-tetrachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.1(6,9).0(2,13).0(5,10)]octadecane-7,8,15,16-tetraone；(1R,2R,5R,6R,9S,10S,13S,14S)-1,6,9,14-tetrachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.16,9.02,13.05,10]octadecane-7,8,15,16-tetrone
• 化学式: C₂₂H₂₄Cl₄O₈
• 分子量: 558.24
• InChiKey: AMLVDCZOEMCPNR-OFWOGWNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1α,2β,5α,6β,9β,10α,13β,14α)-1,6,9,14-tetrachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadecane-7,8,15,16-tetraone 、 4,5-二氯邻苯二胺 在 zinc diacetate 作用下， 以 氯苯 为溶剂， 反应 12.0h， 以92%的产率得到(1α,2α,5β,6β,17β,18β,21α,22α)-8,15,24,31-tetraaza-1,6,11,12,17,22,27,28-tetrachloro-33,33,34,34-tetramethoxynonacyclo[20.10.1.1(16,17).0(2,21).0(5,18).0(7,10).0(9,14).0(23,32).0(25,30)]tetratriacontane-7(10),8,10,12,14,23(32),24,26,28,30-decaene
  参考文献：
  名称：

  Quinoxaline-annelated Z-shaped quadruple-bridged orthocyclophanes: synthesis and crystal structures

  摘要：

  A three-step synthesis of nineteen Z-shaped quadruple-bridged [6,6] and [6,4]orthocyclophanes comprising two quinoxaline-based sidewalls are described. The synthesis began from the bis-Diels-Alder adducts B1-B3 followed by ruthenium-promoted oxidation of dichloroetheno-bridges in the adducts to generate a bis-alpha-diketones, which were then condensed with various arene-1,2-diamines (9a-g) to construct sidewalls (phane parts) of Z-shaped quadruple-bridged orthocyclophanes D1-3, D2g, and D3g. Single-crystal structures of six orthocyclophanes (D1a, D2a, D2f, D3f, D2g-alpha, and D3g-alpha) were obtained and revealed that the C-Ar-H center dot center dot center dot pi and pi center dot center dot center dot pi stacking interactions between N-containing arene rings are the major driving force for molecular assembly and crystal packing, in addition to the interactions involving the polar OCH3 groups and the solvate molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.065
• 作为产物：
  描述：

  endo-endo-anti-1,6,7,8,9,14,15,16-octachloro-17,17,18,18-tetramethoxypentacyclo<12.2.1.1^6,9.0^2,13.0^5,10>octadeca-7,15-diene 在 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 72.0h， 以84%的产率得到(1α,2β,5α,6β,9β,10α,13β,14α)-1,6,9,14-tetrachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadecane-7,8,15,16-tetraone
  参考文献：
  名称：

  Synthesis and Luminescence Properties of U-Shaped Polycyclic Molecules Containing Syn-Facial Functionalized Quinoxaline Rings

  摘要：

  [GRAPHICS]Rigid U-shaped molecules containing syn-facially situated quinoxaline rings have been synthesized in three steps, by a combination of the Diels-Alder reaction, the ruthenium-catalyzed oxidation, and the Zn(OAc)(2)-catalyzed condensation of the resulting bis-alpha-diketones with benzene-1,2-diamines. The unsymmetric bis-quinoxalines, with electronically different substituents, and the quinoxaline ring-attached alpha-diketones were also prepared. Their luminescence properties were examined and described.

  DOI：

  10.1021/ol051707z

文献信息

• Synthesis and Luminescence Properties of U-Shaped Polycyclic Molecules Containing Syn-Facial Functionalized Quinoxaline Rings
  作者：Teh-Chang Chou、Kung-Ching Liao、Jin-Ju Lin

  DOI：10.1021/ol051707z

  日期：2005.10.1

  [GRAPHICS]Rigid U-shaped molecules containing syn-facially situated quinoxaline rings have been synthesized in three steps, by a combination of the Diels-Alder reaction, the ruthenium-catalyzed oxidation, and the Zn(OAc)(2)-catalyzed condensation of the resulting bis-alpha-diketones with benzene-1,2-diamines. The unsymmetric bis-quinoxalines, with electronically different substituents, and the quinoxaline ring-attached alpha-diketones were also prepared. Their luminescence properties were examined and described.
• Quinoxaline-annelated Z-shaped quadruple-bridged orthocyclophanes: synthesis and crystal structures
  作者：Teh-Chang Chou、Kung-Ching Liao

  DOI：10.1016/j.tet.2010.10.065

  日期：2011.1

  A three-step synthesis of nineteen Z-shaped quadruple-bridged [6,6] and [6,4]orthocyclophanes comprising two quinoxaline-based sidewalls are described. The synthesis began from the bis-Diels-Alder adducts B1-B3 followed by ruthenium-promoted oxidation of dichloroetheno-bridges in the adducts to generate a bis-alpha-diketones, which were then condensed with various arene-1,2-diamines (9a-g) to construct sidewalls (phane parts) of Z-shaped quadruple-bridged orthocyclophanes D1-3, D2g, and D3g. Single-crystal structures of six orthocyclophanes (D1a, D2a, D2f, D3f, D2g-alpha, and D3g-alpha) were obtained and revealed that the C-Ar-H center dot center dot center dot pi and pi center dot center dot center dot pi stacking interactions between N-containing arene rings are the major driving force for molecular assembly and crystal packing, in addition to the interactions involving the polar OCH3 groups and the solvate molecules. (C) 2010 Elsevier Ltd. All rights reserved.