8-hydroxy-4,7-dimethylcoumarin | 77869-46-6

• 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: 8-hydroxy-4,7-dimethylcoumarin
• 英文别名: 4,7-Dimethyl-8-hydroxy-cumarin；8-hydroxy-4,7-dimethyl-2H-chromen-2-one；8-hydroxy-4,7-dimethylchromen-2-one
• CAS: 77869-46-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: CKKORNGRGZYMOB-UHFFFAOYSA-N

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：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-4,7-dimethylcoumarin 在 palladium on activated charcoal 盐酸 、 三氟甲磺酸 、 potassium tert-butylate 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 丙酮 为溶剂， 反应 64.92h， 生成
  参考文献：
  名称：

  A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone

  摘要：

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02207-3
• 作为产物：
  描述：

  (+/-)-3-hydroxy-3-(2',3'-dimethoxy-4'-methyl)butanoic acid 在 PPA 作用下， 反应 1.0h， 以80%的产率得到8-hydroxy-4,7-dimethylcoumarin
  参考文献：
  名称：

  Mills, Frank D., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1597 - 1600

  摘要：

  DOI：

文献信息

• On the Possibility of Tuning Molecular Edges To Direct Supramolecular Self-Assembly in Coumarin Derivatives through Cooperative Weak Forces: Crystallographic and Hirshfeld Surface Analyses
  作者：Saikat Kumar Seth、Debayan Sarkar、Atish Dipankar Jana、Tanusree Kar

  DOI：10.1021/cg2006343

  日期：2011.11.2

  (lone pair)···π interactions cooperatively take part. The recurring feature of the self-assembly in all the compounds is the appearance of the molecular ribbon through weak hydrogen bonding. These hydrogen bonded ribbons further stacked into molecular layers by π···π forces. The mode of cooperativity of the weak C–H···O and π···π forces is such that they operate in mutually perpendicular directions

  基于取代的香豆素衍生物（四种有机化合物1 - 4）已通过X射线结构研究进行了合成和表征，并对Hirshfeld表面和指纹图进行了详细分析，从而有助于比较分子间相互作用在构建不同的超分子体系结构中的作用。X射线研究表明，在分子堆积中，C·H···O，π···π和羰基（孤对）···π相互作用共同参与。所有化合物中自组装的重复特征是通过弱氢键出现的分子带。这些氢键结合的带在π···π力的作用下进一步堆叠成分子层。弱C–H···O和π···π的协同作用模式是这样的：它们在相互垂直的方向上起作用-氢在分子平面中在其边缘处键合并且π堆积垂直于分子飞机。通过Hirshfeld表面分析对分子间相互作用和晶体堆积进行的研究表明，超过三分之二的紧密接触与弱相互作用有关。Hirshfeld表面和四个香豆素结构的相应指纹图的分解清楚地量化了晶体结构内的相互作用，揭示了每种化合物所经历的相互作用之间的显着相似性。已
• Total synthesis of (±)-pseudopterosin A–F and K–L aglycone
  作者：David C. Harrowven、Melloney J. Tyte

  DOI：10.1016/j.tetlet.2004.01.060

  日期：2004.3

  A total synthesis of (±)-pseudopterosin A–F and K–L aglycone is described in which three aromatic alkylation reactions are used to construct the hexahydrophenalene ring system.

  描述了（±）-伪藻蛋白A-F和K-L糖苷配基的全合成，其中三个芳族烷基化反应用于构建六氢苯并环系统。
• Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4
  作者：A. Srikrishna、P.C. Ravikumar

  DOI：10.1016/j.tet.2006.07.062

  日期：2006.10

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.
• MILLS F. D., J. HETEROCYCL. CHEM., 1980, 17, NO 7, 1597-1600
  作者：MILLS F. D.

  DOI：——

  日期：——
• A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone
  作者：David C Harrowven、Jonathan D Wilden、Melloney J Tyte、Michael B Hursthouse、Simon J Coles

  DOI：10.1016/s0040-4039(00)02207-3

  日期：2001.2

  A short and practical route to the tricyclic core of an unnatural pseudopterosin diastereoisomer is presented. Key features are an arene alkylation with a gamma -methylene-gamma -butyrolactone, viz. 10 --> 14, and an elaborate reduction sequence 14 --> 17 which both proceed diastereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.