3-cyanoacrolein | 20674-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyanoacrolein
• 英文别名: (E)-3-cyanoacroleine；trans-3-Cyanoacrolein；trans-Cyanoacrolein；trans-3-Cyan-acrolein；(E)-4-oxobut-2-enenitrile
• CAS: 20674-69-5
• 化学式: C₄H₃NO
• 分子量: 81.0739
• InChiKey: KLGZZUFCTPLCSG-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  6
• 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：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyanoacrolein 、 4-溴苯胺 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and reactivity of hexahydropyrroloquinolines

  摘要：

  Formal [4+2] cycloaddition of cyclic enamides with imines derived from aromatic amines gave the 4-arylhexahydropyrroloquinoline skeleton in one step as mixtures of diastereoisomers. Aromatic imines derived from formaldehyde and methylglyoxalate also participated in this chemistry, with the latter favouring formation of the endo-cycloadduct. The cycloadducts derived from methylglyoxalate were unstable and fragmented to give highly substituted quinolines under both neutral and basic conditions. Imines derived from 3-cyanoacrolein also underwent cycloaddition and gave an advanced potential precursor to martinellic acid, albeit with poor diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00466-5
• 作为产物：
  描述：

  (2E)-4-hydroxybut-2-enenitrile 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 3-cyanoacrolein
  参考文献：
  名称：

  Nudelman, Abraham; Keinan, Ehud, Synthesis, 1982, # 8, p. 687 - 688

  摘要：

  DOI：

文献信息

• Lewis-acid assisted cross metathesis of acrylonitrile with functionalized olefins catalyzed by phosphine-free ruthenium carbene complex
  作者：Chen-Xi Bai、Xiao-Bing Lu、Ren He、Wen-Zhen Zhang、Xiu-Juan Feng

  DOI：10.1039/b510776h

  日期：——

  The exchange of the PPh3 ligand in the complex [1,3-bis(2,6-dimethylphenyl)4,5-dihydroimidazol-2-ylidene](PPh3)(Cl)2RuCHPh (7) for a pyridine ligand at ambient temperature leads to the formation of the stable phosphine-free carbene ruthenium complex [1,3-bis(2,6-dimethylphenyl)4,5-dihydroimidazol-2-ylidene](C5H5N)2(Cl)2 RuCHPh (8). The resulted ruthenium complex exhibits highly catalytic activity for the cross metathesis of acrylonitrile with various functionalized olefins under mild conditions, and its activity can be further improved by the addition of a Lewis acid such as Ti(OiPr)4. In the mixture products, the Z-isomer predominates.

  在常温下，将[1,3-双(2,6-二甲基苯基)4,5-二氢咪唑-2-亚基](PPh3)(Cl)2RuCHPh (7)中的 PPh3 配体与吡啶配体交换，可形成稳定的无磷碳化钌配合物[1、3-双（2,6-二甲基苯基）4,5-二氢咪唑-2-亚基](C5H5N)2(Cl)2 RuCHPh (8)。生成的钌络合物对丙烯腈与各种官能化烯烃在温和条件下的交叉复分解反应具有很强的催化活性，而且通过添加路易斯酸（如 Ti(OiPr)4），其活性还能得到进一步提高。
• Highly active phosphine-free carbene ruthenium catalyst for cross-metathesis of acrylonitrile with functionalized olefins
  作者：Chen-Xi Bai、Wen-Zhen Zhang、Ren He、Xiao-Bing Lu、Zhi-Qiang Zhang

  DOI：10.1016/j.tetlet.2005.08.062

  日期：2005.10

  The carbene ruthenium complex [1,3-bis(2,6-dimethylphenyl)-4,5-dihydroimidazol-2-ylidene](C5H5N)2(Cl)2RuCHPh (8) was prepared by the reaction of [1,3-bis (2,6-dimethylphenyl)-4,5-dihydroimidazol-2-ylidene](PPh3)(Cl)2RuCHPh (7) with pyridine and used as a highly effective catalyst for the cross-metathesis of acrylonitrile with various functionalized olefins.

  卡宾钌络合物[1,3-双（2,6-二甲基苯基）-4,5-二氢咪唑-2-亚烷基]（C 5 H 5 N）2（Cl）2 RuCHPh（8）的制备[1,3-双（2,6-二甲基苯基）-4,5-二氢咪唑-2-亚烷基]（PPh 3）（Cl）2 RuCHPh（7）与吡啶，用作交叉复分解的高效催化剂丙烯腈与各种官能化烯烃的混合物。
• Magnetically Bistable Nitrenes: Matrix Isolation of Furoylnitrenes in Both Singlet and Triplet States and Triplet 3-Furylnitrene
  作者：Ruijuan Feng、Yan Lu、Guohai Deng、Jian Xu、Zhuang Wu、Hongmin Li、Qian Liu、Norito Kadowaki、Manabu Abe、Xiaoqing Zeng

  DOI：10.1021/jacs.7b08957

  日期：2018.1.10

  photolysis of the corresponding azides. Both are magnetically bistable in cryogenic matrices, as evidenced by the direct observation of the closed-shell singlet state with IR spectroscopy in solid Ne, Ar, Kr, Xe, and N2 matrices (3-40 K) and the triplet state in toluene (10 K) with EPR spectroscopy (32: |D/hc| = 1.48 cm-1 and |E/hc| = 0.029 cm-1; 36: |D/hc| = 1.39 cm-1 and |E/hc|c = 0.039 cm-1). Subsequent

  通过相应叠氮化物的 266 nm 激光光解产生两种简单的酰基硝烯，2-呋喃酰硝基 (2) 和 3-呋喃酰硝基 (6)。两者在低温基质中都是磁双稳态的，这可以通过在固体 Ne、Ar、Kr、Xe 和 N2 基质 (3-40 K) 中用红外光谱直接观察闭壳单线态和在甲苯中的三线态来证明（ 10 K）与 EPR 光谱（32：|D/hc| = 1.48 cm-1 和 |E/hc| = 0.029 cm-1；36：|D/hc| = 1.39 cm-1 和 |E/hc|c = 0.039 cm-1)。随后的可见光和紫外激光照射分别导致异氰酸呋喃酯（3 和 7）和开环产物 3-氰基丙烯醛（9-E 和 9-Z）的形成，其中难以捉摸的 3-呋喃基腈 (38)还通过 IR 和 EPR 光谱（|D/hc| = 1.12 cm-1 和 |E/hc| = 0.005 cm-1）进行鉴定。
• Oxonitriles: Multicomponent Grignard Addition–Alkylations
  作者：Fraser F. Fleming、Zhiyu Zhang、Qunzhao Wang、Omar W. Steward

  DOI：10.1002/anie.200352920

  日期：2004.2.20
• FARINA F.; GOMEZ M. J.; MARTIN M. V., AN. QUIM. REAL SOC. ESP. FIS Y QUIM. <ANQU-BU>, 1974, 70, NO 12, 900-904
  作者：FARINA F.、 GOMEZ M. J.、 MARTIN M. V.

  DOI：——

  日期：——