2,5-bis(trifluoromethanesulfonyloxy)bicyclo[2.2.2]octa-2,5-diene | 850409-78-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2,5-bis(trifluoromethanesulfonyloxy)bicyclo[2.2.2]octa-2,5-diene
• 英文别名: [5-(Trifluoromethylsulfonyloxy)-2-bicyclo[2.2.2]octa-2,5-dienyl] trifluoromethanesulfonate
• CAS: 850409-78-8
• 化学式: C₁₀H₈F₆O₆S₂
• 分子量: 402.292
• InChiKey: CPKLKXDOYCCDSD-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±45.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,5-bis(trifluoromethanesulfonyloxy)bicyclo[2.2.2]octa-2,5-diene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride Chiralcel OJ 作用下， 以 乙醚 、 正己烷 、 异丙醇 为溶剂， 反应 8.0h， 生成 (1R,4R)-2,5-二苯基二环[2.2.2]辛-2,5-二烯
  参考文献：
  名称：

  C 2对称双环[2.2.2] octa-2,5-二烯配体的制备及其在铑催化的芳基硼酸不对称1,4-加成中的应用

  摘要：

  通过双环[2.2.2]辛烷-2,5-对映体纯制备C 2对称的在2和5位含有苄基，苯基和取代的苯基的双环[2.2.2] octa-2,5-二烯。二酮作为关键中间体。这些手性二烯配体已成功应用于铑催化的芳基硼酸向α，β-不饱和酮的不对称1,4-加成反应。除了环状和线性底物外，还观察到高对映选择性（高达99％ee）以及高催化活性。

  DOI：

  10.1021/jo047831y
• 作为产物：
  描述：

  2-Chloro-5-trimethylsilyloxybicyclo[2.2.2]oct-5-ene-2-carbonitrile 在 sodiumsulfide nonahydrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 59.0h， 生成 2,5-bis(trifluoromethanesulfonyloxy)bicyclo[2.2.2]octa-2,5-diene
  参考文献：
  名称：

  LOW-MOLECULAR COMPOUND, POLYMER, MATERIAL FOR ELECTRONIC DEVICES, COMPOSITION FOR ELECTRONIC DEVICES, ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC SOLAR CELL ELEMENT, DISPLAY AND LIGHTING EQUIPMENT

  摘要：

  公开号：

  EP2495229B1

文献信息

• Tuning the Chiral Environment of <i>C</i>₂-Symmetric Diene Ligands: Development of 3,7-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes
  作者：Ryo Shintani、Yoshitaka Ichikawa、Keishi Takatsu、Fu-Xue Chen、Tamio Hayashi

  DOI：10.1021/jo802437h

  日期：2009.1.16

  analysis of bicyclo[3.3.1]nona-2,6-dienes, new C2-symmetric chiral diene ligands 1 based on 3,7-disubstituted bicyclo[3.3.1]nona-2,6-diene framework have been designed and synthesized. These chiral ligands readily bind to rhodium(I) and provide a different chiral environment from the existing chiral dienes. The rhodium complexes thus obtained act as effective catalysts for 1,4-addition of alkenyl-

  通过对双环[3.3.1] nona-2,6-二烯的结构分析，基于3,7-二取代双环[3.3.1] nona-2,6-diene骨架的新的C 2对称手性二烯配体1具有设计和合成。这些手性配体易于与铑（I）结合并提供与现有手性二烯不同的手性环境。如此获得的铑配合物可作为烯基-和芳基硼酸的1，4-加成到各种α，β-不饱和酮上的有效催化剂，包括以前难以提供高对映选择性的几种组合。
• Asymmetric Conjugate Alkynylation of Cyclic α,β-Unsaturated Carbonyl Compounds with a Chiral Diene Rhodium Catalyst
  作者：Xiaowei Dou、Yinhua Huang、Tamio Hayashi

  DOI：10.1002/anie.201509778

  日期：2016.1.18

  Asymmetric conjugate alkynylation of cyclic α,β‐unsaturated carbonyl compounds (ketones, esters, and amides) was realized by use of diphenyl[(triisopropylsilyl)ethynyl]methanol as an alkynylating reagent in the presence of a rhodium catalyst coordinated with a new chiral diene ligand (Fc‐bod; bod=bicyclo[2.2.2]octa‐2,5‐diene, Fc=ferrocenyl) to give high yields of the corresponding β‐alkynyl‐substituted

  环状α，β-不饱和羰基化合物（酮，酯和酰胺）的不对称共轭烷基化反应是通过在有新型手性二烯配位的铑催化剂存在下，用二苯基[（三异丙基甲硅烷基）乙炔基]甲醇作为烷基化试剂来实现的。配体（Fc-bod； bod =双环[2.2.2] octa-2,5-二烯，Fc =二茂铁基）得到高收率的ee -95％至98％的相应β-炔基取代的羰基化合物。
• LOW-MOLECULAR COMPOUND, POLYMER, ELECTRONIC-DEVICE MATERIAL, COMPOSITION FOR ELECTRONIC DEVICE, ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC SOLAR CELL ELEMENT, DISPLAY AND LIGHTING
  申请人：Urano Toshiyuki

  公开号：US20120193617A1

  公开（公告）日：2012-08-02

  A subject for the invention is to provide compounds where a film formation can be made by a wet film formation method, a heating temperature at the film formation is low, the film formed therefrom has high stability, and the other layers can be laminated thereon by a wet film formation method or another method. The compounds are usable as a material for electronic device which decreases little in charge transport efficiency or luminescent efficiency and which have excellent driving stability. The invention resides in a compound and a polymer which are characterized by having a elimination group of a specific structure and in an organic compound characterized by having a elimination group having a low elimination temperature.
• Preparation of <i>C</i>₂-Symmetric Bicyclo[2.2.2]octa-2,5-diene Ligands and Their Use for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids
  作者：Yusuke Otomaru、Kazuhiro Okamoto、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/jo047831y

  日期：2005.4.1

  C2-Symmetric bicyclo[2.2.2]octa-2,5-dienes containing benzyl, phenyl, and substituted phenyl groups at 2 and 5 positions were prepared enantiomerically pure by way of bicyclo[2.2.2]octane-2,5-dione as a key intermediate. These chiral diene ligands were successfully applied to rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. High enantioselectivity (up to 99%

  通过双环[2.2.2]辛烷-2,5-对映体纯制备C 2对称的在2和5位含有苄基，苯基和取代的苯基的双环[2.2.2] octa-2,5-二烯。二酮作为关键中间体。这些手性二烯配体已成功应用于铑催化的芳基硼酸向α，β-不饱和酮的不对称1,4-加成反应。除了环状和线性底物外，还观察到高对映选择性（高达99％ee）以及高催化活性。
• LOW-MOLECULAR COMPOUND, POLYMER, MATERIAL FOR ELECTRONIC DEVICES, COMPOSITION FOR ELECTRONIC DEVICES, ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC SOLAR CELL ELEMENT, DISPLAY AND LIGHTING EQUIPMENT
  申请人：Mitsubishi Chemical Corporation

  公开号：EP2495229B1

  公开（公告）日：2016-06-01