1,2-丁二烯醛 | 53268-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2-丁二烯醛
• 英文名称: buta-2,3-dienal
• 英文别名: 1,2-Butadienal
• CAS: 53268-92-1
• 化学式: C₄H₄O
• 分子量: 68.0752
• InChiKey: OYBQILSQCOWJHL-UHFFFAOYSA-N

物化性质

• 沸点：
  107.7±7.0 °C(Predicted)
• 密度：
  0.794±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-丁二烯醛 生成 丁烯酮
  参考文献：
  名称：

  HAKIKI, ABDELHAK;RIPOLL, J. -L.;THUILLIER, A., BULL. SOC. CHIM. FR., 1985, N 5, 911-920

  摘要：

  DOI：
• 作为产物：
  描述：

  16-methylidenetetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carbaldehyde 生成 1,2-丁二烯醛
  参考文献：
  名称：

  Retrodienic reactions XVI - flash thermolytic generation of reactive functional allenes

  摘要：

  DOI：

  10.1016/s0040-4039(01)91046-9

文献信息

• Preparation of Cobaloxime-Substituted Unsaturated Carbonyl Compounds and Their Subsequent Conversion into 1-Cobaloxime-Substituted 1,3-Dienyl Complexes
  作者：Brittany L. Hayes、Torrey A. Adams、Kerry A. Pickin、Cynthia S. Day、Mark E. Welker

  DOI：10.1021/om000230m

  日期：2000.7.1

  or β,γ-unsaturated ketones and aldehydes. Two of the new unsaturated acyl complexes prepared have been characterized by X-ray crystallography. Several of the α,β-unsaturated acyl complexes were subsequently converted into 1-cobaloxime-1,3-dienyl complexes using Peterson or Petasis olefinations. One of these new dienyl complexes has also been characterized by X-ray crystallography.

  还原的钴肟化合物（cobaloxime = [（吡啶）（二甲基乙二肟）2钴]）化合物与各种氧取代的烯丙基和炔丙基亲电试剂反应，生成钴肟取代的α，β-或β，γ-不饱和酮和醛。制备的两种新的不饱和酰基配合物已通过X射线晶体学表征。随后，使用Peterson或Petasis烯烃化反应将几种α，β-不饱和酰基络合物转化为1-cobaloxime-1,3-dienyl络合物。这些新的二烯基络合物之一也已经通过X射线晶体学表征。
• Selective Inhibition of Bovine Plasma Amine Oxidase by Homopropargylamine, a New Inactivator Motif
  作者：Chunhua Qiao、Heung-Bae Jeon、Lawrence M. Sayre

  DOI：10.1021/ja049568o

  日期：2004.6.1

  activated allylic amines are known to inactivate the quinone-dependent plasma amine oxidases, possibly through active-site modification by the alpha,beta-unsaturated aldehyde turnover products. Although homopropargylamine (1-amino-3-butyne, 1) is a nonobvious candidate as a mechanism-based inhibitor, 1 was found to be an unusually potent time- and concentration-dependent irreversible inactivator of bovine

  已知炔丙胺和活化的烯丙胺会使醌依赖性血浆胺氧化酶失活，这可能是通过 α、β-不饱和醛周转产物的活性位点修饰来实现的。尽管高炔丙​​胺 (1-amino-3-butyne, 1) 作为基于机制的抑制剂是一种非显而易见的候选物，但发现 1 是一种异常有效的时间和浓度依赖性的牛血浆胺氧化酶 (BPAO) 不可逆灭活剂，表现出30 分钟 IC(50) 2.9 microM 在 30 摄氏度 ([BPAO] = 1.2 microM)。变性失活酶保留的辅因子氧化还原活性表明失活 1 涉及在酶变性后逆转的辅因子修饰或活性位点残基的修饰。因为 1 的失活可能涉及反应性 2 的酶烷基化，制备了 1, 醛 3 的 3-丁缩醛转换产物的 3-丁二烯醛 (3) 互变异构体，发现它可以使 BPAO 失活，但仅在高浓度下。此外，虽然巯基乙醇的存在减弱了 3 的抑制作用，但没有观察到对 1 的这种保护。制备了其转换应直接导致
• Isomeric and tautomeric [C₄H₄O]^+• ions; their thermochemistry and collisionally induced fragmentation characteristics
  作者：Peter C. Burgers、John L. Holmes、F. P. Lossing、Alexander A. Mommers、Frank R. Povel、Johan K. Terlouw

  DOI：10.1139/v82-319

  日期：1982.9.1

  Ionic heats of formation and collisional activation (CA) mass spectra for fifteen isomeric or tautomeric [C4H4O]+• ions are described. Twelve of these species can be characterised by means of their CA mass spectra alone. The relative thermodynamic stabilities of keto–enol tautomers and the ease of interconversion of some ions are discussed. It is emphasised that CA spectra alone (i.e. in the absence

  描述了 15 种异构或互变异构 [C4H4O]+• 离子的离子形成热和碰撞活化 (CA) 质谱。这些物种中有 12 种可以仅通过它们的 CA 质谱来表征。讨论了酮-烯醇互变异构体的相对热力学稳定性和一些离子相互转化的难易程度。需要强调的是，单独的 CA 谱图（即没有其他信息，例如形成热等）可能不容易与适当的离子结构相关联。
• Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones
  作者：Ronald L. Blankespoor、Robert P. Smart、Eric D. Batts、Alan A. Kiste、Rebecca E. Lew、Marc E. Van der Vliet

  DOI：10.1021/jo00126a040

  日期：1995.10

  The facile production of acid sensitive aldehydes and ketones via photochemical intramolecular delta-hydrogen atom transfer in 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones (1) was investigated. Irradiation of 1 in argon purged methanol generates the primary photoproducts, 1-(RCH(OMe)O)-and 1-(ArCH(OMe)O)-9,10-antharahydroquinones (2), respectively. Upon exposure to air, the intermediate anthrahydroquinone is rapidly converted to the corresponding aldehyde and 1-hydroxy-9,10-anthraquinone (3), which can be recycled. Aldehydes containing an acetal or ketal were prepared in high yields using this photoprocess. Apparent rate constants for the photodemethylation of 1-methoxy-2-X-9,10-anthraquinones (X = H, Me, Et, Pr, Bu, i-Bu, and benzyl) were measured and found to vary by a factor of 10 separating the slowest anthraquinone (X = H) and the fastest (X = benzyl), indicating a strong dependency upon the size of the substituent at the a-position. These rate constants are ascribed to equilibrium populations of confonmers in the geometry required for reaction in the n,pi* triplet state.
• Hakiki, Abdelhak; Ripoll, Jean-Louis; Thuillier, Andre, Bulletin de la Societe Chimique de France, 1985, # 5, p. 911 - 920
  作者：Hakiki, Abdelhak、Ripoll, Jean-Louis、Thuillier, Andre

  DOI：——

  日期：——