5,7-二羟基-4-苯基-3,4-二氢色烯-2-酮 | 108013-15-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 5,7-二羟基-4-苯基-3,4-二氢色烯-2-酮
• 英文名称: 3,4-Dihydro-5,7-dihydroxy-4-phenylcoumarin
• 英文别名: 5,7-dihydroxy-4-phenyl-chroman-2-one；5,7-dihydroxy-4-phenylchroman-2-one；5,7-Dihydroxy-4-phenyl-chroman-2-on；5,7-Dihydroxy-4-phenyl-2-chromanone；5,7-dihydroxy-4-phenyl-3,4-dihydrochromen-2-one
• CAS: 108013-15-6
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: RRWANTVEMKYDHW-UHFFFAOYSA-N

物化性质

• 熔点：
  211 °C
• 沸点：
  451.6±45.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 5,7-二羟基-4-苯基-3,4-二氢色烯-2-酮 在 whole E_. coli cells harboring MiCGTb-GAGM 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 以7.3%的产率得到6-(C-β-D-glucosyl)-3,4-Dihydro-4-phenyl-5,7-dihydroxycoumarin
  参考文献：
  名称：

  Biocatalytic C-Glucosylation of Coumarins Using an Engineered C-Glycosyltransferase

  摘要：

  The enzymatic synthesis of coumarin C-glucosides by an engineered C-glycosyltransferase, MiCGTb-GAGM, was explored in vitro and in vivo. MiCGTb-GAGM exhibited a robust C-glucosylation capability toward structurally diverse coumarin derivatives. The whole-cell bioconversion of MiCGTb-GAGM was exploited for large-scale production of coumarin C-glucosides. Two C-glucosides exhibited potent SGLT2 inhibitory activities with IC50 values at 10(-6) M. These findings provide cost-effective and practical synthetic strategies to generate structurally diverse and novel bioactive coumarin C-glycosides for drug discovery.

  DOI：

  10.1021/acs.orglett.8b00378
• 作为产物：
  描述：

  肉桂醛 在 铁酞菁 、 3,3',5,5'-四叔丁基-4,4'-联苯醌 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-甲氧基-3-硝基三氟甲苯 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 16.0h， 生成 5,7-二羟基-4-苯基-3,4-二氢色烯-2-酮
  参考文献：
  名称：

  通过好氧氧化NHC催化N-酰化恶唑烷酮

  摘要：

  报道了使用好氧氧化NHC催化合成有用的恶唑烷酮与醛的第一个N-酰化反应。该反应以良好至优异的产率提供了广泛范围的官能化的恶唑烷酮。仔细选择电子传递介体被证明对实现有效的好氧N酰化至关重要，以前证明使用NHC催化是困难的。该方法允许温和地进入酰化的恶唑烷酮，避免使用危险的和反应性的预官能化底物。

  DOI：

  10.1021/acs.joc.8b01723

文献信息

• Fast and efficient synthesis of flavanones from cinnamic acids
  作者：Kibrom Gebreheiwot Bedane、Runner R. T. Majinda、Ishmael B. Masesane

  DOI：10.1080/00397911.2016.1228110

  日期：2016.11.16

  ABSTRACT A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3 · OEt2 to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones

  摘要 已经开发出一种从肉桂酸中分三步快速有效地合成黄烷酮的方法。首先，使用 SOCl2 将肉桂酸转化为肉桂酰氯化物。然后用 BF3·OEt2 中的取代酚处理酰氯，得到 42 种相应的查耳酮（产率 75%。在室温下碱催化环化查耳酮得到相应的黄酮，产率 85-95%。肉桂酸的转化发现相应查耳酮的衍生物对芳环上取代基的位置和性质很敏感。
• The Michael Reaction of N-Cinnamoylazoles with Phenols. A Simple Synthesis of 4-Arylchroman-2-ones and 1-Arylbenzo[f]chroman-3-ones
  作者：Giovanna Speranza、Carlo F. Morelli、Paolo Manitto

  DOI：10.1055/s-2000-6233

  日期：——

  4-Arylchroman-2-ones 3 and 1-arylbenzo[f]chroman-3-ones 6 have been prepared in moderate to good yields by reaction of dihydric or trihydric phenols with p-substituted N-cinnamoylazoles in dichloromethane under reflux in the presence of DBU.

  4-芳基色满-2-酮3和1-芳基苯并[f]色满-3-酮6已通过将二羟基或三羟基苯酚与对位取代的N-肉桂酰基吡唑在二氯甲烷中回流并在DBU存在下反应，以中等至良好的产率制备。
• An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis
  作者：Jian-Ming Lee、Tsui-Hwa Tseng、Yean-Jang Lee

  DOI：10.1055/s-2001-18436

  日期：——

  A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.

  描述了一种基于高产量的蒙脱石K-10催化的内酯环形成环化过程的合成新黄酮类化合物的新方法。通过制备取代的4-苯基新黄酮1-8，展示了该方法的应用价值。评估了这些物质的自由基清除特性。观察到模拟七叶亭类抗氧化剂的新黄酮1和5能清除羟自由基。
• Parallel synthesis of 2-alkoxy and 2-acyloxyphenylpropyl amides and amines using dihydrocoumarins as versatile synthons. Application of a novel resin quench-capture method
  作者：Jacqueline C. Bussolari、Diana C. Rehborn、Donald W. Combs

  DOI：10.1016/s0040-4039(98)02598-2

  日期：1999.2

  preparation of libraries of 2-substituted phenylpropyl amines and amides was accomplished using dihydrocoumarins as a useful synthon in parallel synthesis. Resin quench methods were utilized in the purifications of the amides and a resin quench-capture method was utilized in metallo-organic reductions leading to the targeted phenylpropyl amines.

  使用二氢香豆素作为平行合成中的有用合成子，完成了溶液相合成，用于制备2-取代的苯基丙胺和酰胺的文库。在酰胺的纯化中使用树脂淬灭方法，在金属有机还原中使用树脂淬灭捕获方法，得到目标苯丙胺。
• Miyano; Matsui, Bulletin of the Chemical Society of Japan, 1958, vol. 31, p. 398,401
  作者：Miyano、Matsui

  DOI：——

  日期：——