2-oxo-2-vinylethanal | 16979-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxo-2-vinylethanal
• 英文别名: acrylaldehyde；vinylglyoxal；3-Butenal, 2-oxo-；2-oxobut-3-enal
• CAS: 16979-06-9
• 化学式: C₄H₄O₂
• 分子量: 84.0746
• InChiKey: SDQVYUNYDAWYIK-UHFFFAOYSA-N

物化性质

• 沸点：
  88.4±13.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-oxo-2-vinylethanal 在 [TripCH2N2(NMe)C2Ph]RuHCl(p-cymene) 、 氢气 作用下， 以 二氯甲烷-D2 为溶剂， 50.0 ℃ 、405.33 kPa 条件下， 反应 2.0h， 以100%的产率得到正丁醛
  参考文献：
  名称：

  半夹心氢化钌（ii）：末端，内部，环状和官能化烯烃的氢化†

  摘要：

  使双（1,2,3-三唑基亚烷基）银（I）配合物1a与[RuCl 2（p- Cymene）] 2反应，得到钌配合物[PhCH 2 N 2（NMe）C 2（C 6 H 4 CF 3）] RuCl 2（p- Cymene）（2a）作为次要的C（sp 2）–H活化副产物[PhCH 2 N 2（NMe）C 2（C 6 H 3 CF 3）] RuCl （p -cymene）（2a'）。类似的钌配合物2b，2c，2d和2e，通式为RuCl 2（对-cymene）（NHC）（NHC = MesCH 2 N 2（NMe）C 2 Ph 2b，PhCH 2 N 2（NMe）C 2 Ph 2c，还合成了TripCH 2 N 2（NMe）C 2 Ph 2d，IMes 2e。Me 3 SiOSO 2 CF 3与2a的后续反应和2b产生阳离子钌物种[[PhCH 2 N 2（NMe）C 2（C 6 H 4 CF 3））RuCl（p

  DOI：

  10.1039/c4dt02407a

文献信息

• Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach
  作者：Lizhi Zhu、Congshan Zhou、Wei Yang、Shuzhong He、Gui-Juan Cheng、Xinhao Zhang、Chi-Sing Lee

  DOI：10.1021/jo401105q

  日期：2013.8.16

  efficient dual-mode Lewis acid induced Diels–Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization

  诱导的狄尔斯-阿尔德（DA）的温和和有效的双模路易斯酸/ carbocyclization级联环化反应已被用于建筑的三环核心的开发耳鼻喉科-kaurenoids一锅与理论研究对π的辅助下，σ-各种路易斯酸的路易斯酸度。以ZnBr 2为双模路易斯酸，一系列取代的烯酮和二烯在室温下顺利进行了DA /碳环化级联环化反应，并在一锅中提供了高收率和高非对映选择性的三环环化产物。三环环化产物已成​​功地用作（±）-Platensimycin和（±）-platencin形式合成的常用中间体。
• Enantioselective Metal/Organo-Catalyzed Aerobic Oxidative sp³C–H Olefination of Tertiary Amines Using Molecular Oxygen as the Sole Oxidant
  作者：Gen Zhang、Yunxia Ma、Shoulei Wang、Yaohu Zhang、Rui Wang

  DOI：10.1021/ja303333k

  日期：2012.8.1

  An organocatalysis/copper-catalyzed asymmetric oxidative sp(3) C-H olefination reaction of tertiary amines with olefins using molecular oxygen as the sole oxidant under mild conditions was realized for the first time. This novel strategy provides an efficient and environmentally friendly way to access diversify optically active C(1)-alkene tetrahydroisoquinoline derivatives.

  首次实现了在温和条件下使用分子氧作为唯一氧化剂的叔胺与烯烃的有机催化/铜催化不对称氧化 sp(3) CH 烯化反应。这种新颖的策略提供了一种有效且环保的方式来获取多样化的光学活性 C(1)-烯烃四氢异喹啉衍生物。
• N-Heterocyclic Carbene-Catalyzed Homoenolate Additions with N-Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ-Lactam Oxindoles
  作者：Bo Zhang、Peng Feng、Li-Hui Sun、Yuxin Cui、Song Ye、Ning Jiao

  DOI：10.1002/chem.201201375

  日期：2012.7.23

  In pole position: A simple and efficient approach to spirocyclic γ‐lactam oxindoles by the N‐heterocyclic carbene catalyzed addition of homoenloate equivalents to N‐aryl isatinimines has been developed (see scheme). The use of N‐aryl isatinimines as electrophiles in the NHC‐catalyzed umpolung reaction of α,β‐unsaturated aldehydes is demonstrated for the first time.

  处于极点位置：已开发出一种简单有效的方法，通过N杂环卡宾催化的均烯酸酯等效物加成到N芳基异亚丁烯酮中来合成螺环γ-内酰胺ox（见方案）。首次证明了在NHC催化的α，β-不饱和醛的umpolung反应中使用N-芳基异亚胺作为亲电子试剂。
• VO(acac)2: An Efficient Catalyst for the Oxidation of Aldehydes to the Corresponding Acids in the Presence of Aqueous H2O2
  作者：Ashim Thakur、Dhrubajyoti Talukdar、Kiran Sharma、Saitanya Bharadwaj

  DOI：10.1055/s-0032-1316914

  日期：——

  VO(acac)(2) catalyzes the oxidation of aldehydes (aromatic, aliphatic, and heterocyclic) to the corresponding acids efficiently and selectively in the presence of H2O2 as an oxidant. This method possesses functional-group compatibility, easy workup procedure, and shorter reaction time. The reaction is highly dependent on the solvent used. Performance of titania-supported VO(acac)(2) in the oxidation of aldehyde was also investigated.
• Design, synthesis, and docking studies of novel ofloxacin analogues as antimicrobial agents
  作者：S. Jubie、P. Prabitha、R. Rajesh Kumar、R. Kalirajan、R. Gayathri、S. Sankar、K. Elango

  DOI：10.1007/s00044-011-9655-8

  日期：2012.7

  A number of novel ofloxacin analogues were synthesized by modifying the carboxylic acid at C-6. To investigate the antimicrobial data on structural basis, in-silico docking studies of the tested compounds into the crystal structure of topoisomerase II using Autodock vina 4.0 program was performed in order to predict the affinity and orientation of the synthesized compounds at the activities. R (2) values show good agreement with predicted binding affinities obtained by molecular docking studies. Also, it is verified by in-vitro antimicrobial screening, where all the compounds were most active against Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis. Among these compounds 3a, 3b, 3f showed good MIC (0.125 mu g/ml).