Bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbaldehyde | 72602-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: Bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbaldehyde
• CAS: 72602-65-4
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: YWQKONLUTRCJRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbaldehyde 在 氢气 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Acid mediated intramolecular cyclization of π-donors bearing two vicinal “cis”-branched, 1,4-dithiafulven-6-yl substituents on a CC bond

  摘要：

  Cis-ethylenic analogues 1 and ortho-benzenic analogues 2 of TTF undergo a rapid acid mediated intramolecular cyclization into the corresponding cycloisomers 1' and 2' whose structures are confirmed by X-ray diffraction; as shown by cyclic voltammetry, compounds 1 may act as convenient precursors of organic metals.

  DOI：

  10.1016/s0040-4039(00)60363-5
• 作为产物：
  描述：

  2-丁炔二醛 以72%的产率得到
  参考文献：
  名称：

  GORGUES A.; COG A. LE, J. CHEM. SOC. CHEM. COMMUN., 1979, NO 17, 767-768

  摘要：

  DOI：

文献信息

• Versatilite de reactivite de l`acetylene dicarbaldehyde et des aldehydes α-acetyleniques a l'egard des dienes conjugues cycliques et heterocycliques en milieu acide
  作者：A. Gorgues、A. Simon、A. Le Coq、A. Hercouet、F. Corre

  DOI：10.1016/s0040-4020(01)87436-6

  日期：1986.1

  of acetylenedicarbaldehyde and the corresponding mono acetal is described. A comparison of their reactivity with other α-acetylenic aldehydes R-CC-CHO to towards conjugated cydic or hetero- cydic dienes is presented. Under neutral conditions, the only expected Diels-Alder adducts are formed. Under acidic conditions (HCO2H, CF3,CO2H or eventually AcOH) they afford the only Diel-Alder adduct when the

  描述了乙炔二甲醛和相应的单缩醛的制备。它们与其它α-炔醛RCC-CHO的反应性的比较来向共轭cydic或异cydic二烯被呈现。在中性条件下，仅形成预期的Diels-Alder加合物。在酸性条件下（HCO 2 H，CF 3，CO 2 H或最终为AcOH），当环丁二烯不表现出任何芳族特征时，它们会提供唯一的Diel-Alder加合物，而在相反的情况下，Michael加成物或多或少重要数量; 从呋喃开始，还可以观察到第三个途径来处理双亲电子取代化合物的形成。的机制进行了讨论和特别地，共用偶极的中间为竞争形成建议帐户和。
• Acetylenedicarbaldehyde: isolation and some examples of exclusive dienophilicity under neutral conditions
  作者：Dominique Stéphan、Alain Gorgues、Ahmed Belyasmine、André Le Coq

  DOI：10.1039/c39880000263

  日期：——

  Acetylenedicarbaldehyde (1) is isolated in the pure state after acidolysis of its monoacetal (2) with an excess of formic acid followed by dehydration of residual HCO2H into CO with P2O5; under neutral conditions, (1) reacts with conjugated dienes as a dienophile only, in contrast to what occurs in acidic medium.

  在用过量的甲酸酸解其单缩醛（2），然后用P 2 O 5将残留的HCO 2 H脱水成CO时，分离出纯的乙炔二甲醛（1）; 在中性条件下，（1）与共轭二烯仅作为亲二烯体反应，这与酸性介质中的反应相反。
• A useful synthon: acetylenedicarbaldehyde (but-2-ynedial)
  作者：Alain Gorgues、Andr� Le Coq

  DOI：10.1039/c39790000767

  日期：——

  The preparation of acetylenedicarbaldehyde (but-2-ynedial)(2) and its electrophilic properties towards some dienes are reported; the usefulness of the two aldehyde groups in the adducts obtained is exemplified by a Wittig reaction and the synthesis of a pyridazine.

  报道了乙炔基二甲醛（but-2-ynedial）（2）的制备及其对某些二烯的亲电性能。所获得的加合物中两个醛基的有用性以维蒂希反应和哒嗪的合成为例。
• Unexpected Formation of Dienes in the Diels−Alder Reaction of Exocyclic 1-Bromobutadienes of Polycyclic Hydrocarbons
  作者：Sergio Cossu、Giancarlo Cuomo、Ottorino De Lucchi、Michele Maggini、Giovanni Valle

  DOI：10.1021/jo951434t

  日期：1996.1.1

  Polycyclic dienes having an exocyclic 1-bromobutadiene moiety react with dienophiles and fullerene-C-60 to afford exclusively dienes via a cycloaddition-elimination mechanism. Neither the primary adducts nor the double addition products derived from a second cycloaddition of the dienophile to the diene could be detected. In one case only, i.e. with 4-phenyl-1,2,4-triazoline-3,5-dione, was the double addition product formed. Contrary to expectations, X-ray diffractometric analysis shows that this adduct is formed following a contrasteric approach.
• GORGUES A.; COQ A., TETRAHEDRON LETT., 1979, NO 50, 4829-4832
  作者：GORGUES A.、 COQ A.

  DOI：——

  日期：——