2-乙酰基-3-氧代丁腈 | 3141-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基-3-氧代丁腈
• 英文名称: 2-acetyl-3-oxo-butyronitrile
• 英文别名: 3-cyanopentane-2,4-dione；3-Cyan-pentandion-(2,4)；α-cyanoacetylacetone；3-cyano-2,4-pentanedione；2-acetyl-3-oxobutanenitrile
• CAS: 3141-59-1
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: ORMIKPSLLOLDGT-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  158.2±20.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-乙酰基-3-氧代丁腈 在 ammonium hydroxide 作用下， 反应 2.0h， 以58%的产率得到2-amino-3-cyano-2-penten-4-one
  参考文献：
  名称：

  Vibrational assignment and structure of 4-amino-3-cyano-3-penten-2-one

  摘要：

  Fourier transform infrared and Fourier transform Raman spectra of 4-amino-3-cyano-3-penten-2-one and its deuterated analogue have been obtained. Density functional theory (DFT) B3LYP and G96LYP calculations have been carried out with the purpose of understanding the vibrational spectra of this compound and its deuterated analogue. Vibrational wavenumbers calculated by B3LYP/6-31G* (with a p shell added on the amine protons) force field are closed with the experimental results. The percentage of deviation of the bond lengths and bond angles gives a good picture of the normal modes, and serves as a basis for the assignment of the wavenumbers. The calculated geometrical parameters show a strong intramolecular hydrogen bond with a N...O distance of 2.605-2.622 Angstrom. This bond length is about 0.04-0.06 Angstrom shorter than that in its parent, 4-amino-3-penten-2-one (with no cyano substitution in the alpha-position). Experimental evidences also indicate presence of an intermolecular hydrogen bond in the solid state, completely, and in solution, partially. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(02)00179-5
• 作为产物：
  描述：

  3-acetyl-2-imino-4-oxo-valeronitrile 在 sodium hydroxide 作用下， 生成 2-乙酰基-3-氧代丁腈
  参考文献：
  名称：

  Traube, Chemische Berichte, 1898, vol. 31, p. 2943

  摘要：

  DOI：

文献信息

• Anodic Cyanation of β-Dicarbonyl Compounds
  作者：Mitsuhiro Okimoto、Kaori Numata、Yukio Takahashi、Masayuki Hoshi、Kenta Tomozawa、Takamasa Shigemoto

  DOI：10.1055/s-2005-872685

  日期：——

  β-dicarbonyl compounds were electrochemically oxidized in a methanolic solution in the presence of sodium cyanide and sodium methoxide to yield the corresponding α-cyano-β-dicarbonyl compounds in moderate to good yields. Presumably, a two-electron transfer transforms the anion derived from the β-dicarbonyl compounds into a cation, which then reacts with a cyanide ion to afford the cyanation products.

  在氰化钠和甲醇钠的存在下，几种β-二羰基化合物在甲醇溶液中被电化学氧化，以中等至良好的产率产生相应的α-氰基-β-二羰基化合物。据推测，双电子转移将衍生自 β-二羰基化合物的阴离子转化为阳离子，然后与氰化物离子反应得到氰化产物。
• Zirconium complexes with the trifunctional 3-cyanopentane-2,4-dionate ligand
  作者：George A. Lock、David W. Thompson

  DOI：10.1039/dt9800001265

  日期：——

  Five zirconium complexes containing the 3-cyanopentane-2,4-dionate and 2-cyano-1-phenylbutane-1,3-dionate ligands (L) have been prepared: [ZrCl2(C6H6NO2)2], [ZrCl2(C11H8NO2)2], [ZrCl(C6H6NO2)3], [Zr(C6H6NO2)4], and [Zr(η-C5H5)(C6H6NO2)3]. Infrared data shows that all β-diketonate ligands are co-ordinated to the metal centre through both oxygens; however, in complexes of the type [ZrCl2L2] and [ZrCIL3]

  已经制备了五个含有3-氰基戊烷-2,4-二酸酯和2-氰基-1-苯基丁烷-1,3-二酸酯配体（L）的锆配合物：[ZrCl 2（C 6 H 6 NO 2）2 ]， [使用ZrCl 2（C 11 H ^ 8 NO 2）2 ]，[使用ZrCl（C 6 H ^ 6 NO 2）3 ]，[Zr的（C 6 H ^ 6 NO 2）4 ]和[Zr的（η-C 5 H ^ 5）（C 6 H 6 NO 2）3]。红外数据表明，所有的β-二酮酸酯配体都通过两个氧与金属中心配位。然而，在[ZrCl 2 L 2 ]和[ZrCIL 3 ]类型的络合物中，氰基也似乎是配位的。
• Lanthanide Catalyzed Synthesis of β-Hydroxyl Amides
  作者：P. Zhou、N. R. Natale

  DOI：10.1080/00397919808004440

  日期：1998.9

  Abstract Lanthanide (III) chloride improved the reaction of carboxylic esters with β-amino alkoxides (generated in situ from β-amino alcohols) and produced β-hydroxyl amides under mild conditions, and in high yields.

  摘要 镧系元素 (III) 氯化物改进了羧酸酯与 β-氨基醇盐（由 β-氨基醇原位生成）的反应，并在温和的条件下以高产率制备了 β-羟基酰胺。
• D-π-A-π-D Dyes with a 1,3,2-Dioxaborine Cycle in the Polymethine Chain: Efficient Long-Wavelength Fluorophores
  作者：Vladyslav Polishchuk、Mariia Stanko、Andrii Kulinich、Mykola Shandura

  DOI：10.1002/ejoc.201701466

  日期：2018.1.17

  nonsymmetric derivatives. The synthesis of dyes with various electron donor termini [indole, benzothiazole, pyran, 4-(dialkylamino)phenyl] and with different polymethine chain lengths is reported. The obtained compounds show intense absorption and fluorescence in the red and NIR region, their fluorescence brightness (the product of the molar extinction and the fluorescence quantum yield) attaining a value

  新合成的 5-cyano-2,2-difluoro-4,6-dimethyl-1,3,2-dioxaborine 中的腈基显示出显着增加甲基的酸度。这使得花青与两个甲基基团缩合形成 D–π–A–π–D 染料，其中二恶硼啉循环是聚甲炔链的一部分。在那里，半产物中剩余甲基的反应性降低到足以逐步进行反应，从而获得非对称衍生物。报告了具有各种电子供体末端 [吲哚、苯并噻唑、吡喃、4-(二烷基氨基)苯基] 和具有不同聚次甲基链长的染料的合成。所得化合物在红色和近红外区域显示出强烈的吸收和荧光，它们的荧光亮度（摩尔消光和荧光量子产率的乘积）达到 200,000 m–1 cm–1 的值。它们的特点是小规模的正溶剂化变色，但它们的荧光量子产率对环境极性更敏感。已经进行了时间相关 (TD)DFT 计算来研究新二氧杂环戊二烯的电子结构并揭示这些分子中长波长电子跃迁的性质。
• Bimetallic coordination networks based on Al(acacCN)3: a building block between inertness and lability
  作者：Carina Merkens、Nils Becker、Kevin Lamberts、Ulli Englert

  DOI：10.1039/c2dt30623a

  日期：——

  The Al(III) complex of 3-cyanopentane-2,4-dionate (acacCN) features peripheric nitrile groups which may coordinate to silver cations. As the Al(acacCN)3 building block ranges between inertness and lability, its reactivity towards Ag(I) salts depends on the solvent and the weakly or non-coordinating counter anions; an impressive range of different extended structures has been encountered. With AgPF6, the original building block is retained and hexafluorophosphate remains uncoordinated. A highly symmetric 3D crystalline solid forms in the presence of trichloromethane, and with benzene a tetrasolvate with large solvent-filled voids is obtained. Two different classes of reaction products with silver triflate have been observed. In addition to networks incorporating Al(acacCN)3, partial solvolysis may lead to a dinuclear methoxide-bridged derivative. The resulting Al2(μ-OMe)2 core may be perceived as a four-connected node in a self-interpenetrating 3D network. Earlier studies reported transmetalation for the reaction of Al(acacCN)3 with AgNO3 and we find the same reactivity for silver tetrafluoroborate. Full degradation of the Al(III) building block with formation of [Ag(acacCN)] is observed.

  3-氰基戊烷-2,4-二酸酯 (acacCN) 的 Al(III) 络合物具有可与银阳离子配位的外围腈基团。由于 Al(acacCN)3 结构单元介于惰性和不稳定之间，因此其对 Ag(I) 盐的反应性取决于溶剂和弱配位或非配位阴离子；我们遇到了一系列令人印象深刻的不同扩展结构。对于 AgPF6，原始结构单元被保留，六氟磷酸盐仍然不配位。在三氯甲烷存在下形成高度对称的 3D 结晶固体，并与苯一起获得具有大的溶剂填充空隙的四溶剂化物。已经观察到与三氟甲磺酸银的两种不同类型的反应产物。除了包含 Al(acacCN)3 的网络外，部分溶剂分解可能会产生双核甲醇桥联衍生物。由此产生的 Al2(μ-OMe)2 核可以被视为自互穿 3D 网络中的四连接节点。早期研究报道了 Al(acacCN)3 与 AgNO3 反应的金属转移，我们发现四氟硼酸银具有相同的反应性。观察到 Al(III) 结构单元完全降解并形成 [Ag(acacCN)]。