2-quinoxalinecarboxaldehyde dimethylacetal | 434318-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-quinoxalinecarboxaldehyde dimethylacetal
• 英文别名: 2-(dimethoxymethyl)quinoxaline
• CAS: 434318-22-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: AZPYYYMRJDNUMX-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  280.4±35.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-quinoxalinecarboxaldehyde dimethylacetal 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 4-nitro-N-(quinoxalin-2-ylmethylideneamino)benzamide
  参考文献：
  名称：

  A simple quinoxaline-based highly sensitive colorimetric and ratiometric sensor, selective for nickel and effective in very high dilution

  摘要：

  A new quinoxaline based receptor (HQNM) has been designed and synthesized which shows a remarkable color change from colorless to yellow on specific binding with nickel. The cation recognition property of the receptor is monitored by the UV-vis and H-1 NMR titrations. It is observed that the receptor shows a specific selectivity toward nickel over other interfering cations. Thus, a significant bathochromic shift in UV-vis spectrum with a sharp yellow color in 'naked-eye' makes the receptor suitable for the easy detection of nickel ion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.051
• 作为产物：
  描述：

  1,1-二甲氧基丙酮 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 2-quinoxalinecarboxaldehyde dimethylacetal
  参考文献：
  名称：

  A simple quinoxaline-based highly sensitive colorimetric and ratiometric sensor, selective for nickel and effective in very high dilution

  摘要：

  A new quinoxaline based receptor (HQNM) has been designed and synthesized which shows a remarkable color change from colorless to yellow on specific binding with nickel. The cation recognition property of the receptor is monitored by the UV-vis and H-1 NMR titrations. It is observed that the receptor shows a specific selectivity toward nickel over other interfering cations. Thus, a significant bathochromic shift in UV-vis spectrum with a sharp yellow color in 'naked-eye' makes the receptor suitable for the easy detection of nickel ion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.051

文献信息

• Multifold Bond Cleavage and Formation between MeOH and Quinoxalines (or Benzothiazoles): Synthesis of Carbaldehyde Dimethyl Acetals
  作者：Yunkui Liu、Bo Jiang、Wei Zhang、Zhenyuan Xu

  DOI：10.1021/jo302450f

  日期：2013.2.1

  2-quinoxalinyl (or 2-benzothiazolyl) carbaldehyde dimethyl acetals has been achieved. 2-Quinoxalinyl carbaldehyde dimethyl acetals were readily converted into 2-quinoxalinyl carbaldehydes in good to excellent yields under acidic conditions. Preliminary mechanistic studies suggest that the reaction proceeds via multifold bond cleavage and formation between methanol and N-heterocycles involving a dioxygen-participated

  已经实现了由AK 2 S 2 O 8介导的喹喔啉（或苯并噻唑）与甲醇的直接交叉偶联反应，从而生成了2-喹喔啉基（或2-苯并噻唑基）甲醛二甲基乙缩醛。在酸性条件下，2-喹喔啉基甲醛二甲基乙缩醛易于以良好或优异的收率转化成2-喹喔啉基甲醛。初步的机理研究表明，该反应是通过多重键裂解和甲醇与N-杂环之间的形成而进行的，涉及双氧参与的自由基过程。该方法可以通过简单的N的交叉偶联直接合成各种2-喹喔啉基（或2-苯并噻唑基）甲醛二甲基乙缩醛。-在无醛，无酸和无过渡金属的条件下，杂环C–H键和甲醇。
• The Smallest Vicinal Tricarbonyl Compound as a Monohydrate and Tetracarbonyl Compound as a Thiane Derivative - First Effective Synthesis, Characterization and Chemistry
  作者：Shyamaprosad Goswami、Annada C. Maity、Hoong-Kun Fun、Suchada Chantrapromma

  DOI：10.1002/ejoc.200801050

  日期：2009.3

  The synthesis of a series of protected as well as free heterocyclic aldehydes (pterins and quinoxalines) by the use of the appropriate tricarbonyl compounds is also reported. Additionally, a one-step synthetic strategy to prepare a series of different biheterocycles with the smallest vicinal tetracarbonyl compound is demonstrated.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  报道了 2-oxo-1,3-propanedial 一水合物或 mesoxaldehyde (6a) 的有效合成和 2,3-dioxo-1,4-butanedial (18) 作为噻烷衍生物的首次合成。最小的邻位三和四羰基化合物的这些第一成员通过转化为噻烷衍生物 8、9、10、11、12、15 和 19 来稳定，这些衍生物可以在室温下作为长寿命化合物分离。这些新型噻烷 8、10、12 和 15 的结构通过它们的 X 射线晶体结构得到证实。还报道了使用适当的三羰基化合物合成一系列受保护和游离的杂环醛（蝶呤和喹喔啉）。此外，还展示了用最小的邻位四羰基化合物制备一系列不同二杂环的一步合成策略。
• Molybdenum pentachloride (MoCl5) or molybdenum dichloride dioxide (MoO2Cl2): advanced catalysts for thioacetalization of heterocyclic, aromatic and aliphatic compounds
  作者：Shyamaprosad Goswami、Annada C. Maity

  DOI：10.1016/j.tetlet.2008.03.048

  日期：2008.5

  A new, convenient and mild method for thioacetalization of heterocyclic, aromatic and aliphatic compounds catalyzed by MoCl(5) or MoO(2)Cl(2) is described. This novel method is important for the synthesis of the difficult to prepare heterocyclic thioacetals such as the pterin thioacetals and it offers significant advantages such as high conversion, short reaction times and simplicity in operation. (C) 2008 Elsevier Ltd. All rights reserved.
• Biocatalytic Oxidation of 2-Methylquinoxaline to 2-Quinoxalinecarboxylic Acid
  作者：John W. Wong、Harry A. Watson,、James F. Bouressa、Michael P. Burns、James J. Cawley、Albert E. Doro、Donald B. Guzek、Michael A. Hintz、Ellen L. McCormick、Douglas A. Scully、Joseph M. Siderewicz、William J. Taylor、Susan J. Truesdell、Richard G. Wax

  DOI：10.1021/op025501e

  日期：2002.7.1

  A microbial process using the fungus Absidia repens ATCC 14849 is described for the oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. A campaign consisting of three 14000-L runs produced 20.5 kg of the acid with a 28% overall yield. The bioconversion gave a lower yield compared with a three step chemical synthesis (35%), but was carried out in one pot, and avoided safety issues with a di-N-oxide intermediate. Although successfully scaled to produce kilograms of 2-quinoxalinecarboxylic acid for synthesis of a drug candidate, the A. repens bioconversion is unsuitable for further scale-up due to low product concentration (similar to1 g/L). A second microbial process using Pseudomonas putida ATCC 33015 is also described for the oxidation of 2-methylquinoxaline. The P. putida bioconversion gave an 86% in situ yield at 8-L scale and yielded a product concentration approximately 10-fold greater than that of the A. repens bioconversion.
• A simple quinoxaline-based highly sensitive colorimetric and ratiometric sensor, selective for nickel and effective in very high dilution
  作者：Shyamaprosad Goswami、Shampa Chakraborty、Sima Paul、Sandipan Halder、Annada C. Maity

  DOI：10.1016/j.tetlet.2013.07.051

  日期：2013.9

  A new quinoxaline based receptor (HQNM) has been designed and synthesized which shows a remarkable color change from colorless to yellow on specific binding with nickel. The cation recognition property of the receptor is monitored by the UV-vis and H-1 NMR titrations. It is observed that the receptor shows a specific selectivity toward nickel over other interfering cations. Thus, a significant bathochromic shift in UV-vis spectrum with a sharp yellow color in 'naked-eye' makes the receptor suitable for the easy detection of nickel ion. (C) 2013 Elsevier Ltd. All rights reserved.