十四烷-7,8-二酮 | 6305-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十四烷-7,8-二酮
• 英文名称: tetradecane-7,8-dione
• 英文别名: 7,8-tetradecanedione
• CAS: 6305-47-1
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: ZSKKAJLPNIHYRI-UHFFFAOYSA-N

物化性质

• 熔点：
  38-39 °C
• 沸点：
  291.5±9.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  十四烷-7,8-二酮 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 ammonium acetate 、 potassium carbonate 、 溶剂黄146 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 72.83h， 生成
  参考文献：
  名称：

  D–π–A–π–A featured dyes containing different electron-withdrawing auxiliary acceptors: The impact on photovoltaic performances

  摘要：

  Four novel D-pi-A-pi-A metal-free organic dyes Q1-Q4 were synthesized and the impacts of the auxiliary acceptors on the photovoltaic performances were studied. Q2 with quinoxaline as the auxiliary acceptor exhibited the best photovoltaic performance due to its highest short-circuit photocurrent density (17.22 mA cm(-2)), leading to a power conversion efficiency of 7.42% under simulated AM 1.5 G illumination. Q1 with the strongest electron withdrawing group (pyrazino[2,3-gjquinoxaline) as the auxiliary acceptor showed the weakest performance, which can be attributed to electron trap and mismatch of energy-level. The results showed that the different electron-withdrawing property of auxiliary units significantly influenced the absorption, energy levels and photovoltaic performance. Incorporating auxiliary acceptor with moderate electron-deficient ability can extend the absorption range and adjust the molecular orbital energy levels, resulting in better photovoltaic performance. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.04.001
• 作为产物：
  描述：

  庚酸甲酯 以 四氢呋喃 为溶剂， 以63%的产率得到十四烷-7,8-二酮
  参考文献：
  名称：

  脂族酯的阴极偶联。合成1,2-二酮和酰基里昂的有用反应

  摘要：

  在这项研究中已经发现，使用Mg电极对脂肪族酯（1）进行电还原会导致在非质子传递条件下形成相应的1,2-二酮，而进行还原时，通过酰胆碱缩合可以生成双（三甲基甲硅烷基氧基）烯烃。在三甲基氯硅烷存在下脱除。

  DOI：

  10.1016/0040-4039(95)00899-n

文献信息

• Lewis acid assisted permanganate oxidations
  作者：Sheng Lai、Donald G. Lee

  DOI：10.1016/s0040-4020(02)01227-9

  日期：2002.12

  Lewis acids combine with permanganate in acetone solutions to form a complex that has enhanced oxidizing capabilities. The use of Lewis acids under these conditions to promote permanganate oxidations is superior to the use of Bronsted acids because the latter promote enolization of the solvent and subsequent unproductive reduction of the oxidant. The products obtained from a variety of alkenes, alkynes

  路易斯酸与高锰酸盐在丙酮溶液中结合形成具有增强的氧化能力的复合物。在这些条件下使用路易斯酸来促进高锰酸盐氧化优于使用布朗斯台德酸，因为后者会促进溶剂的烯化和随后的氧化剂的无用还原。已经鉴定了从各种烯烃，炔烃，芳烃，硫化物，醇和醚中获得的产物，并提出了可能的反应机理。
• A Simple and Improved Procedure for the Conversion of Alkynes to 1,2-Diketones by Indirect Electrooxidation With Ruthenium Tetroxide as a Mediator
  作者：Sigeru Torii、Tsutomu Inokuchi、Youzou Hirata

  DOI：10.1055/s-1987-27950

  日期：——

  Indirect electrooxidation of alkynes 1 using ruthenium tetroxide as a mediator, leading to 1,2-diones 2 in 72-87%, is described. The electrolysis is carried out in the presence of a catalytic amount of ruthenium dioxide dihydrate in a two phase system of saturated aqueous sodium chloride and carbon tetrachloride. The overoxidation of 1,2-diones to the corresponding carboxylic acid, an unavoidable drawback generally encountered in the metal oxidation of acetylenes, is suppressed greatly by maintaining the pH of the aqueous phase at 4 and conducting the reaction at 0-5°C. The synthetic utility of this electrochemical oxidation is exemplified by the preparation of 2i (82%), a key intermediate for the synthesis of furaneol 4, from the commercially available 1i.

  使用四氧化钌作为介质，对炔烃1进行间接电氧化，以72-87%的产率得到1,2-二酮2。电解在含有催化量二氧化钌二水合物的水和四氯化碳两相体系中进行，使用饱和氯化钠水溶液。通过将水相的pH维持在4，并在0-5°C下进行反应，可以大大抑制1,2-二酮过氧化成相应的羧酸，这是通常在金属氧化炔烃中遇到的一个不可避免的缺点。这种方法的合成实用性通过从市售的1i制备关键中间体2i（产率82%）来证明，2i是合成furaneol 4的重要中间体。
• Poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline): Processible, Low-Bandgap, Ambipolar-Acceptor Frameworks via Direct Arylation Polymerization
  作者：Seth Rasmussen、Trent Anderson、Evan Culver、Furqan Almyahi、Paul Dastoor

  DOI：10.1055/s-0037-1610299

  日期：2018.12

  The synthesis of a new dialkyl-functionalized quinoxaline ­acceptor, 5,8-dibromo-2,3-dihexylquinoxaline, is reported, along with its cross-coupling with 2,3-dihexylthieno[3,4-b]pyrazine via direct arylation polymerization. The resulting ambipolar-acceptor polymer ­poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline) exhib­its a low bandgap of 1.07 eV and high solubility. The results of

  报道了一种新的二烷基官能化喹喔啉受体 5,8-二溴-2,3-二己基喹喔啉的合成，以及它与 2,3-二己基噻吩并 [3,4-b] 吡嗪通过直接芳基化聚合的交叉偶联. 所得双极性受体聚合物聚 (2,3-二己基噻吩并 [3,4-b] 吡嗪-alt-2,3-二己基喹喔啉) 具有 1.07 eV 的低带隙和高溶解度。还报告了初始有机光伏器件的结果。
• Catalytic Action of Azolium Salts. VI. Preparation of Benzoins and Acyloins by Condensation of Aldehydes Catalyzed by Azolium Salts.
  作者：Akira MIYASHITA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.42.2633

  日期：——

  Benzoins 4 (2-hydroxyethanones substituted with aryl groups at the 1- and 2-positions) were prepared by self-condensation of aromatic aldehydes 3 using catalytic amounts of azolium salts 1 and 2 in excellent yields.1, 3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the preparation of acyloins 6 (2-hydroxyethanones substituted with alkyl groups at the 1- and 2-positions) by self-condensation of aliphatic aldehydes 5. On the other hand, an attempt at the condensation of hexanal (5d) catalyzed by 1, 3-dimethylimidazolium iodide (1) failed to yield the acyloin 6d, and instead the aldol-type condensed product 8d was obtained.

  苯偶姻 4（在 1- 和 2-位置上带有芳基取代的 2-羟基乙酮）通过使用少量的唑盐 1 和 2 作为催化剂，由芳香醛 3 的自缩合反应高效制备得到。1,3-二甲基苯并咪唑碘盐（2）是制备乙偶姻 6（在 1- 和 2-位置上带有烷基取代的 2-羟基乙酮）的有效催化剂，通过脂肪醛 5 的自缩合反应实现。另一方面，使用 1,3-二甲基咪唑碘盐（1）催化己醛（5d）的缩合反应未能得到乙偶姻 6d，而是得到了醛醇型缩合产物 8d。
• Samarium diiodide promoted formation of 1,2-diketones and 1-acylamido-2-substituted benzimidazoles from N-acylbenzotriazoles
  作者：Xiaoxia Wang、Yongmin Zhang

  DOI：10.1016/s0040-4020(03)00575-1

  日期：2003.6

  N-Acylbenzotriazoles, when treated with samarium diiodide in THF, undergo self-coupling reaction to afford 1,2-diketones in good to excellent yields; while when treated with samarium diiodide in CH3CN, they undergo ring-opening reaction to afford 1-acylamido-2-alkyl (or aryl) benzimidazoles in reasonable to good yields. A plausible mechanism was suggested.

  N-酰基苯并三唑在THF中用二碘化sa处理时，会发生自偶联反应，从而以良好或极好的收率得到1,2-二酮；当在CH 3 CN中用二碘化sa处理时，它们会发生开环反应，以合理至良好的收率获得1-酰氨基-2-烷基（或芳基）苯并咪唑。提出了一个合理的机制。