7-acetoxy-3-bromo-4-methylcoumarin | 69019-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-acetoxy-3-bromo-4-methylcoumarin
• 英文别名: 3-bromo-4-methyl-2-oxo-2H-chromen-7-yl acetate；7-Acetoxy-3-brom-4-methyl-cumarin；(3-bromo-4-methyl-2-oxochromen-7-yl) acetate
• CAS: 69019-74-5
• 化学式: C₁₂H₉BrO₄
• 分子量: 297.105
• InChiKey: YGIREYIDWSUFCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-acetoxy-3-bromo-4-methylcoumarin 在 三氯化铝 、 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 硝基苯 、 乙腈 为溶剂， 生成 3-Bromo-7-hydroxy-4-methyl-chromene-2-thione
  参考文献：
  名称：

  Gadre; Audi; Karambelkar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 1, p. 60 - 62

  摘要：

  DOI：
• 作为产物：
  描述：

  7-乙酰氧基-4-甲基香豆素 在 N-氯代丁二酰亚胺 、 copper(II) choride dihydrate 、 zinc(II) chloride 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以85.2%的产率得到7-acetoxy-3-bromo-4-methylcoumarin
  参考文献：
  名称：

  使用 N-卤代琥珀酰亚胺作为卤化物源的铜卤化物促进香豆素的区域选择性卤化

  摘要：

  据报道，使用金属卤化物（单独的 CuX2 或与 ZnX2）促进卤化，以 N-卤代琥珀酰亚胺（NXS）作为卤化物源，安全、方便和区域选择性地合成 3-卤香豆素。该合成涉及通过铜或锌与 N-卤代琥珀酰亚胺的配位以及随后缺电子香豆素的亲电芳香取代，在原位稳定生成高活性正卤素 (X+)。该程序也适用于以中等至定量产率卤化含电子量较低的萘醌、黄酮和甲氧基补骨脂素。该协议具有简单的实验条件，使用容易获得的廉价试剂，并为一些有用的杂芳族化合物的氯化或溴化提供了方便的方法。

  DOI：

  10.1055/s-0037-1612080

文献信息

• An efficient regioselective bromination protocol of activated coumarins using 2,4,4,6-tetrabromo-2,5-cyclohexadienone
  作者：Nemai C. Ganguly、Subhasis Nayek、Sumanta Chandra

  DOI：10.1139/cjc-2013-0230

  日期：2013.11

  2,4,4,6-Tetrabromo-2,5-cyclohexadienone mediated bromination of a wide assortment of activated coumarins in acetonitrile has been accomplished with high regioselectivity and good to excellent yields. The selectivity and efficiency of bromination were found to be markedly dependent on electronic factors, particularly degree of electron withdrawal from electron-releasing 7-oxygenated substituents to the C-3 position of the α-pyrone moiety by vinylogous resonance and the presence of nucleophilic additives such as water and tetra-n-butylammonium bromide in the reaction medium. The sole by-product of the reaction was converted back to the reagent by oxidation with KBr−KBrO₃, which was recycled three times without significant loss of efficiency.

  在乙腈中，2,4,4,6-四溴-2,5-环己二酮介导的对活化香豆素的溴化反应以高区域选择性和良好至优良的产率完成。发现溴化的选择性和效率在很大程度上取决于电子因素，特别是从电子给予的7-氧代取代基到α-吡喃酮部分的C-3位置的电子撤离程度，通过共轭共振和在反应介质中存在水和四正丁基溴化铵等亲核添加剂。反应的唯一副产物通过氧化与KBr−KBrO₃转化回试剂，试剂可以循环使用三次而不会显著损失效率。
• Synthesis and biological activity of meso-tetrakis (2,10-dioxo-2H, 10H-pyrano [2,3-f] chromene-9-yl) porphyrins
  作者：V. Naveen Kumar、Y. Thirupathi Reddy、P. Narasimhareddy、B. Rajitha、E. De Clercq

  DOI：10.3998/ark.5550190.0007.f22

  日期：——

  Synthesis of meso-tetrakis (2, 10-dioxo-2H, 10H-pyrano[2,3-f] chromene-9-yl) porphyrins are synthesized directly by reaction of pyrrole with substituted 4-methyl-2,10-dioxo-2H, 10Hpyrano[2,3-f]chromene-9-carbaldehydes in dichloromethane / acid media. The aldehyde’s molar ratio was controlled to optimize the synthesis and purification of the desired porphyrins. This new series of porphyrins was characterized

  meso-tetrakis (2, 10-dioxo-2H, 10H-pyrano[2,3-f] chromene-9-yl) 卟啉的合成是通过吡咯与取代的 4-methyl-2,10-dioxo-反应直接合成的二氯甲烷/酸介质中的 2H, 10Hpyrano[2,3-f]chromene-9-carbaldehydes。控制醛的摩尔比以优化所需卟啉的合成和纯化。这个新系列的卟啉通过 TLC、质谱（FAB 质量）、H NMR、UV 和 IR 进行表征
• Sehgal; Seshadri, Journal Of Scientific and Industrial Research, 1953, vol. 12 B, p. 346,348
  作者：Sehgal、Seshadri

  DOI：——

  日期：——
• A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions
  作者：Hai-Ming Guo、Fujie Tanaka

  DOI：10.1021/jo900013w

  日期：2009.3.20

  We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.