rac-(1R,4S,4aS,4bS,5S,8R,8aS,10aS)-1,2,3,4,5,6,7,8-octachloro-11,11,12,12-tetramethoxy-1,4,4a,4b,5,8,8a,10a-octahydro-1,4:5,8-dimethanophenanthrene | 138768-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-(1R,4S,4aS,4bS,5S,8R,8aS,10aS)-1,2,3,4,5,6,7,8-octachloro-11,11,12,12-tetramethoxy-1,4,4a,4b,5,8,8a,10a-octahydro-1,4:5,8-dimethanophenanthrene
• CAS: 138768-11-3
• 化学式: C₂₀H₁₈Cl₈O₄
• 分子量: 605.985
• InChiKey: XLQNBNCZWXCCAK-NUCQHSGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  rac-(1R,4S,4aS,4bS,5S,8R,8aS,10aS)-1,2,3,4,5,6,7,8-octachloro-11,11,12,12-tetramethoxy-1,4,4a,4b,5,8,8a,10a-octahydro-1,4:5,8-dimethanophenanthrene 在 sodium 、 对甲苯磺酸 、 叔丁醇 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 rac-(3aR,4R,4aR,8aS,9S,9aS)-3a,4,4a,8a,9,9a-hexahydro-1H-4,9-ethenocyclopenta[b]naphthalen-1-one
  参考文献：
  名称：

  Diels-alder环加成-应付重排方法构建C s和C 2对称六环二十碳四烯

  摘要：

  s-和C 2-六环杂环四烯酮2通过九步反应序列合成，总产率为15-20％，由1用作顺式9、10-二氢萘当量和1,2,3,4-四氯-5 ，5-二甲氧基环戊二烯为环戊二烯酮当量。

  DOI：

  10.1016/0040-4039(91)80167-5
• 作为产物：
  描述：

  5,5-二甲氧基-1,2,3,4-四氯环戊二烯 、 (1β,2α,7α,8β)-1,8,9,10-tetrachloro-11,11-dimethoxy<6.2.1.0^2,7>undec-3,5,9-triene 以 甲苯 为溶剂， 以83%的产率得到rac-(1R,4S,4aS,4bS,5S,8R,8aS,10aS)-1,2,3,4,5,6,7,8-octachloro-11,11,12,12-tetramethoxy-1,4,4a,4b,5,8,8a,10a-octahydro-1,4:5,8-dimethanophenanthrene
  参考文献：
  名称：

  Diels-alder环加成-应付重排方法构建C s和C 2对称六环二十碳四烯

  摘要：

  s-和C 2-六环杂环四烯酮2通过九步反应序列合成，总产率为15-20％，由1用作顺式9、10-二氢萘当量和1,2,3,4-四氯-5 ，5-二甲氧基环戊二烯为环戊二烯酮当量。

  DOI：

  10.1016/0040-4039(91)80167-5

文献信息

• 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.