2-(2',3'-dihydroxypropyl)quinoxaline | 32706-29-9

• 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-(2',3'-dihydroxypropyl)quinoxaline
• 英文别名: 2-(2',3'-Dihydroxypropyl)-quinoxaline；3-quinoxalin-2-ylpropane-1,2-diol
• CAS: 32706-29-9
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: BCVPBVHFMBXVQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  415.1±40.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  66.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-deoxy-2-pentulose 、 邻苯二胺 以 various solvent(s) 为溶剂， 反应 3.0h， 以58%的产率得到2-(2',3'-dihydroxypropyl)quinoxaline
  参考文献：
  名称：

  Characterization of precursors and elucidation of the reaction pathway leading to a novel coloured 2H,7H,8aH-pyrano[2,3-b]pyran-3-one from pentoses by quantitative studies and application of 13C-labelling experiments

  摘要：

  The intensely coloured (1R,8aR)- and (1S,8aR)-4-(2-furyl)-7-[(2-furyl)methylidene]-2-hydroxy-2H,7H,8aH-pyrano[2,3-b]pyran-3-one (1a/1b) have recently been identified among the main coloured compounds formed in the presence of pentoses. To clarify its formation pathway, quantitative studies on the effectivity of certain carbohydrate degradation products as precursors of 1a/1b were performed indicating the 3-deoxypentose-2-ulose, furan-2-carboxaldehyde and hydroxyacetaldehyde as the penultimate precursors of the colourant. In addition, a labelling experiment with [C-13(1)]-xylose was performed to elucidate how these precursors are transformed into 1a/1b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00280-8

文献信息

• Interaction of (−)-Epigallocatechin Gallate and Deoxyosones Blocking the Subsequent Maillard Reaction and Improving the Yield of <i>N</i>-(1-Deoxy-<scp>d</scp>-xylulos-1-yl)alanine
  作者：Junhe Yu、Heping Cui、Wei Tang、Khizar Hayat、Shahzad Hussain、Muhammad Usman Tahir、Yahui Gao、Xiaoming Zhang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.0c00200

  日期：2020.2.12

  Maillard reaction intermediate formation in the xylose/alanine model system. A trapping effect of EGCG on the reactive deoxyosones was observed to change the reaction pathways. The rate constant of Amadori rearrangement product (ARP) conversion to deoxyosones was decreased with EGCG addition, indicating an inhibition of ARP degradation. Dehydration improved the ARP formation during the thermal reaction

  （-）-表没食子儿茶素没食子酸酯（EGCG）对木糖/丙氨酸模型系统中的美拉德反应中间体的形成有重大影响。观察到EGCG对反应性脱氧肌松蛋白的捕获作用改变了反应途径。加入EGCG会降低Amadori重排产物（ARP）转化为脱氧松酮的速率常数，这表明ARP降解受到抑制。脱水改善了热反应过程中ARP的形成，并协同提高了ARP的收率，并具有对脱氧松质的EGCG捕获作用。此外，EGCG降低了木糖/丙氨酸向ARP转化的活化能（从77.8 kJ / mol至62.8 kJ / mol），进而加速了ARP的形成。在90°C的最佳条件下，pH 7.5时，EGCG的作用进一步增强。
• 3-Deoxypentosulose:  An α-Dicarbonyl Compound Predominating in Nonenzymatic Browning of Oligosaccharides in Aqueous Solution
  作者：Anke Hollnagel、Lothar W. Kroh

  DOI：10.1021/jf011107o

  日期：2002.3.1

  as the route to its formation. 1-Amino-1,4-dideoxyhexosulose could be formed by vinylogous alpha-elimination from the 2,3-enediol structure after Amadori rearrangement, favored by planar alignment of the bonds between C1 and C4. Subsequent rearrangement by keto-enoltautomerization leads to a 1-imino-3-keto structure. In this structure, attack of a hydroxyl anion, provided by water at neutral pH, could

  在焦糖化（无甘氨酸）和美拉德（含甘氨酸）条件下研究了D-葡萄糖，麦芽糖和麦芽三糖在水溶液中的热降解。监测糖和α-二羰基产物的降解。在焦糖化和美拉德反应条件下，3-脱氧戊糖是由麦芽糖和麦芽三糖形成的主要的α-二羰基化合物。然而，在不存在氨基化合物的情况下，以低得多的浓度形成3-脱氧戊糖。结论是3-脱氧戊糖是通过寡糖和多糖特异的途径形成的，因为该α-二羰基是由α-1-> 4葡聚糖如麦芽糖和麦芽三糖形成的，而不是由葡萄糖形成的。在形成过程中，发生了1-氨基-1烯醇化产物的逆Claisen反应，提出了4-二脱氧己糖作为其形成的途径。在Amadori重排后，可以通过2,3-烯二醇结构中的乙烯基α-消除作用形成1-氨基-1,4-二脱氧己糖，这在C1和C4之间的键平面排列中是有利的。随后通过酮-烯醇自体化进行的重排导致了1-亚氨基-3-酮的结构。在这种结构中，由中性pH值的水提供的氢氧根阴离子的侵蚀可能
• Formation of α-Dicarbonyl Compounds in Beer during Storage of Pilsner
  作者：Adriana Bravo、Julio C. Herrera、Erika Scherer、Yon Ju-Nam、Heinrich Rübsam、Jorge Madrid、Carsten Zufall、Rafael Rangel-Aldao

  DOI：10.1021/jf703696p

  日期：2008.6.1

  With the aim of determining the formation of alpha-dicarbonyl intermediates during beer aging on the shelf, alpha-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of alpha-dicarbonyls were evaluated by the quantification of key Strecker aldehydes and by GC-olfactometry (GCO)analysis of beer headspace using solid phase microextraction. Four alpha-dicarbonyls, reported here for the first time, were detected in fresh and aged beers, three were derived from the 2,3-enolization pathway of mono- and disaccharides, and the fourth was derived from the epimerization of 3-deoxy-2-hexosulose. Ten alpha-dicarbonyls were quantified during beer processing and during different periods of beer aging at 28 degrees C. The aging periods were from 15 to 105 days. During beer aging, 1-deoxydiuloses were produced and degraded, while 1,4-dideoxydiuloses were produced at the highest rates. The GCO analysis indicated that forced beer aging increased the amounts of furaneol, trans-2-nonenal, and phenylacetaldehyde. The blockage of alpha-dicarbonyls inhibited the accumulation of sensory-active aldehydes in the beer headspace.
• Morita, Naofumi; Inoue, Keiichi; Hayashi, Hideo, Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2053 - 2060
  作者：Morita, Naofumi、Inoue, Keiichi、Hayashi, Hideo、Takagi, Masanosuke

  DOI：——

  日期：——
• MORITA, NAOFUMI;INOUE, KEIICHI;HAYASHI, HIDEO;TAKAGI, MASANOSUKE, AGR. AND BIOL. CHEM., 1983, 47, N 9, 2053-2059
  作者：MORITA, NAOFUMI、INOUE, KEIICHI、HAYASHI, HIDEO、TAKAGI, MASANOSUKE

  DOI：——

  日期：——