Bicyclo<2.2.2>octa-2,5-diene-2,3-dicarboxylic acid | 30989-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Bicyclo<2.2.2>octa-2,5-diene-2,3-dicarboxylic acid
• 英文别名: Bicyclo<2.2.2>octadien-(2,5)-dicarbonsaeure-(2,3)；Bicyclo[2.2.2]octadien-(2,5)-dicarbonsaeure-(2,3)；Bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylic acid
• CAS: 30989-15-2
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: APTIVUQAUCPVAB-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: water (7732-18-5))
• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.493±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Bicyclo<2.2.2>octa-2,5-diene-2,3-dicarboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以96.5%的产率得到Bicyclo<2.2.2>oct-2-ene-2,3-dicarboxylic acid
  参考文献：
  名称：

  Unusual stereoselectivity in the Diels-Alder addition of cyclopentadiene with the bicyclo[2.2.2]octene nucleus

  摘要：

  Cyclopentadiene adds to the substituted and electronically activated double bond of bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylic anhydride with pronounced endo selectivity. Only two of the four possible stereoisomers were formed. The stereochemical course of the reaction was determined by X-ray crystallography and by a combination of chemical and spectroscopic techniques.

  DOI：

  10.1021/jo00076a039
• 作为产物：
  描述：

  1,3-环己二烯 、 丁炔二酸 以 四氢呋喃 为溶剂， 反应 18.0h， 以91%的产率得到Bicyclo<2.2.2>octa-2,5-diene-2,3-dicarboxylic acid
  参考文献：
  名称：

  Unusual stereoselectivity in the Diels-Alder addition of cyclopentadiene with the bicyclo[2.2.2]octene nucleus

  摘要：

  Cyclopentadiene adds to the substituted and electronically activated double bond of bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylic anhydride with pronounced endo selectivity. Only two of the four possible stereoisomers were formed. The stereochemical course of the reaction was determined by X-ray crystallography and by a combination of chemical and spectroscopic techniques.

  DOI：

  10.1021/jo00076a039

文献信息

• 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.
• [EN] SYNTHESIS OF POLYSUBSTITUTED AROMATIC COMPOUNDS AND AROMATISATION PROCESS FOR USE THEREIN<br/>[FR] SYNTHESE DE COMPOSES AROMATIQUES POLYSUBSTITUES ET PROCEDE D'AROMATISATION POUR CETTE SYNTHESE
  申请人：——

  公开号：WO1999050259A2

  公开（公告）日：1999-10-07

  [EN] In a retro-Diels-Alder reaction the starting cycloadduct is protected by -OH or -OP groups to form a desired benzene derivative or heteroaromatic compound, with the concomitant elimination of a dioxolene species. The protecting groups P are preferably comprised in a cyclic thiocarbonate or cis-isopropyldienedioxy group. The cycloadduct may be prepared by Diels-Alder cycloaddition of an acetylenic dienophile to a cyclohexadiene-cis-diol, and the cyclohexadiene may be formed by biological oxidation of an arene. The process allows desired aromatised products to be produced in uniformly high yields and the reaction is generally initiated at lower temperatures than known methods of synthesis which evolve ethylene. The by-products are usually non-volatile and may spontaneously polymerise.
  [FR] Dans une rétroréaction de Diels-Adler, le groupe de cycloaddition de départ est protégé par des groupes -OH ou OP de façon à former un dérivé benzène attendu ou un composé hétéroaromatique attendu, tout en éliminant une espèce dioxolène. Les groupes de protection P sont de préférence compris dans un groupe thiocarbonate cyclique ou cis-isopropyldiènedioxy. Le groupe de cycloaddition peut être obtenu par cycloaddition Diels-Adler d'un diénophile acétylénique à un cyclohexadiène-cis-diol, le cyclohexadiène pouvant être formé par oxydation biologique d'un arène. Ce procédé permet de produire avec des rendements uniformément élevés des produits aromatisés attendus. La réaction démarre à des températures généralement plus basses que dans le cas des techniques connues de synthèse qui font évoluer l'éthylène. Les sous-produits, qui sont généralement non-volatils, peuvent se polymériser spontanément.
• Unusual stereoselectivity in the Diels-Alder addition of cyclopentadiene with the bicyclo[2.2.2]octene nucleus
  作者：Richard Vaughan Williams、Murali Mohan Reddy Todime、Paul Enemark、Dick van der Helm、Safia Khalil Rizvi

  DOI：10.1021/jo00076a039

  日期：1993.11

  Cyclopentadiene adds to the substituted and electronically activated double bond of bicyclo[2.2.2]octa-2,5-diene-2,3-dicarboxylic anhydride with pronounced endo selectivity. Only two of the four possible stereoisomers were formed. The stereochemical course of the reaction was determined by X-ray crystallography and by a combination of chemical and spectroscopic techniques.