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 | 133008-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 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；(1S,2R,5R,6S,9R,10S,13S,14R)-1,6,7,8,9,14,15,16-octachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.16,9.02,13.05,10]octadeca-7,15-diene
• CAS: 133008-12-5
• 化学式: C₂₂H₂₄Cl₈O₄
• 分子量: 636.054
• InChiKey: BZNOKFWHCFKZSK-OFWOGWNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 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：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 、 5,5-二甲氧基-1,2,3,4-四氯环戊二烯 反应 3.0h， 生成 (1R,2S,5R,6S,9R,10S,13R,14S)-1,6,7,8,9,14,15,16-octachloro-17,17,18,18-tetramethoxypentacyclo[12.2.1.16,9.02,13.05,10]octadeca-7,15-diene 、 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
  参考文献：
  名称：

  1,5-环辛二烯的串联反向电子需求的狄尔斯-阿尔德反应。

  摘要：

  六氯环戊二烯和5,5-二甲氧基-1,2,3,4-四氯环戊-2,4-二烯与1,5-环辛二烯反应以高收率产生1：4的反加成混合物。使用X my检查非对映异构体的立体化学，并使用分子力学计算来探索观察到的非对映选择性的某些潜在原因。

  DOI：

  10.1016/s0040-4039(00)92688-1

文献信息

• Reverse-electron-demand diels-alder dienophile π-face selectivity via conformation dependent transmission of π-σ-π electronic interactions.
  作者：J.Gabriel Garcia、Mark L. McLaughlin

  DOI：10.1016/s0040-4039(00)92689-3

  日期：1991.7

  Reverse-electron-demand Diels-Alder reactions of a series of remotely substituted cyclooctenes with hexachlorocyclopentadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-2,4-diene indicate that dienophile π-face selectivity results from conformation dependent transmission of π-σ-π electronic interactions.

  一系列远程取代的环辛烯与六氯环戊二烯和5,5-二甲氧基-1,2,3,4-四氯环戊-2,4-二烯的反电子需求Diels-Alder反应表明，构象导致了亲二烯体π面选择性π-σ-π电子相互作用的依存传递。
• 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.
• Garcia, J. Gabriel; McLaughlin, Mark L., Organic Preparations and Procedures International, 1995, vol. 27, # 1, p. 92 - 95
  作者：Garcia, J. Gabriel、McLaughlin, Mark L.

  DOI：——

  日期：——
• 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.
• Tandem reverse-electron-demand diels-alder reactions of 1,5-cyclooctadiene.
  作者：J.Gabriel Garcia、Frank R. Fronczek、Mark L. McLaughlin

  DOI：10.1016/s0040-4039(00)92688-1

  日期：1991.7

  Hexachlorocyclopentadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-2,4-diene react with 1,5-cyclooctadiene to produce a 1:4 syn to anti mixture of diadducts in good yield. The stereochemistry of the diastereomers is examined using X my and molecular mechanics calculations are used to explore some of the potential causes for the observed diastereoselectivity.

  六氯环戊二烯和5,5-二甲氧基-1,2,3,4-四氯环戊-2,4-二烯与1,5-环辛二烯反应以高收率产生1：4的反加成混合物。使用X my检查非对映异构体的立体化学，并使用分子力学计算来探索观察到的非对映选择性的某些潜在原因。