5-hydroxy-4,7-dimethylcoumarin | 6335-27-9

• 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: 5-hydroxy-4,7-dimethylcoumarin
• 英文别名: 4,7-dimethyl-5-hydroxy-2H-1-benzopyran-2-one；5-hydroxy-4,7-dimethyl-2H-1-benzopyran-2-one；5,-hydroxy-4,7-dimethyl-2H-chromen-2-one；5-hydroxy-4,7-dimethyl-6-nitrosocoumarin；5-hydroxy-4,7-dimethyl-2H-chromen-2-one；5-hydroxy-4,7-dimethylchromen-2-one
• CAS: 6335-27-9
• 化学式: C₁₁H₁₀O₃
• mdl: MFCD00460712
• 分子量: 190.199
• InChiKey: JJHLYYXMYNBADE-UHFFFAOYSA-N

物化性质

• 熔点：
  248 °C
• 沸点：
  371.3±42.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932209090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,7-dimethylcoumarin 在 chlorosulphuric acid 作用下， 生成 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-sulfonic acid anilide
  参考文献：
  名称：

  Merchant; Shah, Journal of the Indian Chemical Society, 1957, vol. 34, p. 45,49

  摘要：

  DOI：
• 作为产物：
  描述：

  3-acetyl-6-carboethoxy-5-hydroxy-4,7-dimethylcoumarin 在 硫酸 作用下， 反应 0.33h， 以20 mg的产率得到5-hydroxy-4,7-dimethylcoumarin
  参考文献：
  名称：

  Talapatra, Sunil Kumar; Pal, Pijus; Biswas, Kallolmay, Journal of the Indian Chemical Society, 1998, vol. 75, # 10-12, p. 590 - 597

  摘要：

  DOI：

文献信息

• [EN] TRICYCLIC GYRASE INHIBITORS FOR USE AS ANTIBACTERIAL AGENTS<br/>[FR] INHIBITEURS TRICYCLIQUES DE GYRASE UTILISABLES COMME AGENTS ANTIBACTÉRIENS
  申请人：TRIUS THERAPEUTICS INC

  公开号：WO2014043272A1

  公开（公告）日：2014-03-20

  Disclosed herein are compounds having the structure of Formula I and pharmaceutically suitable salts, esters, and prodrugs thereof that are useful as antibacterially effective tricyclic gyrase inhibitors. In addition, species of tricyclic gyrase inhibitors compounds are also disclosed herein. Related pharmaceutical compositions, uses and methods of making the compounds are also contemplated.

  本文披露了具有化学式I结构的化合物及其药用盐、酯和前药，这些化合物可用作抗菌有效的三环酶抑制剂。此外，本文还披露了三环酶抑制剂化合物的种属。还考虑了相关的药用组合物、用途和制备这些化合物的方法。
• TRICYCLIC GYRASE INHIBITORS
  申请人：Bensen Daniel

  公开号：US20120238751A1

  公开（公告）日：2012-09-20

  Disclosed herein are compounds having the structure of Formula I and pharmaceutically suitable salts, esters, and prodrugs thereof that are useful as antibacterially effective tricyclic gyrase inhibitors. Related pharmaceutical compositions, uses and methods of making the compounds are also contemplated.

  本文披露了具有式I结构的化合物，以及作为抗菌有效的三环酶抑制剂的药用盐、酯和前药，相关的药物组合物、用途和制备该化合物的方法也在考虑之中。
• Design, Synthesis, and Biological Evaluation of a Series of 5- and 7-Hydroxycoumarin Derivatives as 5-HT1A Serotonin Receptor Antagonists
  作者：Kinga Ostrowska、Anna Leśniak、Zuzanna Czarnocka、Jagoda Chmiel、Magdalena Bujalska-Zadrożny、Bartosz Trzaskowski

  DOI：10.3390/ph14030179

  日期：——

  new derivatives using microwave-assisted protocols. We show that three new compounds show a relatively high antagonistic activity against the 5HT1A receptor, although lower than the reference compound WAY-100635. These compounds also showed relatively low binding affinities to the 5-HT2A receptor. We also provide a detailed structure–activity analysis of this series of compounds and compare it with previously

  我们已经设计并合成了一系列60种新的带有哌嗪部分的5-和7-羟基香豆素衍生物，它们预期与5-HT 1A和5-HT 2A受体结合。所有研究化合物的分子对接揭示了三个配体的5-HT 1A R K i和一个配体的5-HT 2A R Ki的亚纳摩尔估计以及两个受体的K i的许多低纳摩尔估计。这些结果引起我们的兴趣，我们使用微波辅助方案合成了全部60种新衍生物。我们显示三种新化合物对5HT 1A表现出较高的拮抗活性受体，尽管低于参考化合物WAY-100635。这些化合物对5-HT 2A受体的结合亲和力也较低。我们还提供了该系列化合物的详细结构-活性分析，并将其与先前获得的详尽的香豆素衍生物系列的结果进行了比较。
• Synthesis and Photooxygenation of Linear and Angular Furocoumarin Derivatives as a Hydroxyl Radical Source: Psoralen, Pseudopsoralen, Isopseudopsoralen, and Allopsoralen
  作者：Sameh Ramadan Elgogary、Neveen Mohamed Hashem、Mohamed Nabeel Khodeir

  DOI：10.1002/jhet.2084

  日期：2015.3

  carried out through Williamson reaction of hydroxycoumarins with 3‐chloro‐2‐butanone followed by cyclization with polyphosphoric acid or by heating in a strongly alkaline solution. The photooxygenation reactions of synthesized furocoumarins were performed in chloroform and in the presence of tetraphenylporphyrin as singlet oxygen sensitizer (1O2). The photooxygenation reactions afforded the photocleaved

  通过羟基香豆素与3-氯-2-丁酮的Williamson反应，然后用多磷酸环化或在强碱性溶液中加热，可以合成具有潜在光生物学特征的新型骨架结构的线性和角呋喃香豆素。合成的呋喃香豆素的光氧化反应在氯仿中和在四苯基卟啉作为单线态氧敏剂（1 O 2）存在下进行。光氧合反应通过[2 + 2]环加成反应提供光解产物，通过烯反应和[4 + 2]环加成提供光解产物。分离出光产物并通过光谱分析充分表征。
• Establishing a Flow Process to Coumarin-8-Carbaldehydes as Important Synthetic Scaffolds
  作者：Jaroslav Zak、David Ron、Elena Riva、Heather P. Harding、Benedict C. S. Cross、Ian R. Baxendale

  DOI：10.1002/chem.201201039

  日期：2012.8.6

  Despite their usefulness as fluorophores and synthetic precursors, efficient and reliable routes to coumarin‐8‐carbaldehydes are lacking. We describe here a high‐yielding continuous flow synthesis that requires no manual intermediate purification or work‐up, giving access to multigram quantities of the aldehyde product.

  尽管它们可用作荧光团和合成前体，但仍缺乏高效，可靠的香豆素-8甲醛合成途径。我们在这里描述了一种高产量的连续流合成方法，不需要人工进行中间纯化或后处理，可以得到数克量的醛产品。