(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 | 135821-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 135821-75-9
• 化学式: C₂₂H₂₄Cl₈O₄
• 分子量: 636.054
• InChiKey: BZNOKFWHCFKZSK-NKBPCWSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (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 在 ruthenium trichloride 、 sodium periodate 、 zinc diacetate 、 水 作用下， 以 氯仿 、 氯苯 、 乙腈 为溶剂， 反应 39.0h， 生成 (1α,2β,5β,6α,17α,18β,21β,22α)-8,15,24,31-tetraaza-1,6,17,22-tetrachloro-33,33,34,34-tetramethoxynonacyclo[20.10.1.1^6,17.0^2,21.0^5,18.0^7,10.0^9,14.0^23,32.0^25,30]tetratriacontane-7(10),8,10,12,14,23(32),24,26,28,30-decaene
  参考文献：
  名称：

  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：

  5,5-二甲氧基-1,2,3,4-四氯环戊二烯 、 1,5-环辛二烯 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：

  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

文献信息

• 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。
• 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。
• Preparation, structures and preliminary host–guest studies of fluorinated <i>syn</i>-bis-quinoxaline molecular tweezers
  作者：Markus Etzkorn、Jacob C Timmerman、Matthew D Brooker、Xin Yu、Michael Gerken

  DOI：10.3762/bjoc.6.39

  日期：——

  potential molecular tweezers for electron-rich guest compounds. Our synthetic route to the cyclooctadiene-derived scaffolds 16a-d takes advantage of the facile isolation of a novel spirocyclic precursor 9b with the crucial syn-orientation of its two alkene moieties. The crystal structure of 16c displays two features typical of a molecular tweezer: inclusion of a solvent molecule in the molecular cleft and

  已经制备了一系列具有氟化同面喹喔啉侧壁的多环骨架作为富电子客体化合物的潜在分子镊子。我们的环辛二烯衍生支架 16a-d 的合成路线利用了新型螺环前体 9b 的简便分离及其两个烯烃部分的关键顺向取向。16c 的晶体结构显示出分子镊子的两个典型特征：在分子裂缝中包含溶剂分子和自互补支架的自缔合。此外，溶液中化合物 16c 的主客​​体 NMR 研究表明，未结合和结合的富电子客体 N,N,N',N'-四甲基-对苯二胺之间存在化学交换。