(±)-7-hydroxy-4-phenyl-3,4-dihydrocoumarin | 6275-80-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: (±)-7-hydroxy-4-phenyl-3,4-dihydrocoumarin
• 英文别名: 7-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-2-one；(+/-)-7-hydroxy-4-phenyl-3,4-dihydrocoumarin；3,4-dihydro-4-phenyl-7-hydroxycoumarin；7-hydroxy-3,4-dihydro-4-phenylcoumarin；7-hydroxy-4-phenyl-chroman-2-one；7-Hydroxy-4-phenyl-chroman-2-on；7-Hydroxy-4-phenyl-2-chromanone；7-hydroxy-4-phenyl-3,4-dihydrochromen-2-one
• CAS: 6275-80-5
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: FPHAXRIFTRBSSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-7-hydroxy-4-phenyl-3,4-dihydrocoumarin 在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 3-(2,4-dihydroxyphenyl)-N-(3,3-diphenylpropyl)-3-phenylpropanamide
  参考文献：
  名称：

  Derivatives of arylalkylamines. XXIII. Synthesis of N-arylalkyl-substituted 3-[2,3 (or 2,4)-dihydroxyphenyl]-3-phenylpropylamines and their effect on the uptake of catecholamines

  摘要：

  DOI：

  10.1007/bf00767829
• 作为产物：
  描述：

  7-羟基-4-苯基香豆素 在 sodium amalgam 作用下， 生成 (±)-7-hydroxy-4-phenyl-3,4-dihydrocoumarin
  参考文献：
  名称：

  Clayton et al., Journal of the Chemical Society, 1953, p. 581,584

  摘要：

  DOI：

文献信息

• Highly Efficient and Single Step Synthesis of 4-Phenylcoumarins and 3,4-Dihydro-4-phenylcoumarins Over Montmorillonite K-10 Clay, Under Microwave Irradiation†
  作者：Jasvinder Singh、Jasamrit Kaur、Sandeep Nayyar、Goverdhan L. Kad

  DOI：10.1039/a708103k

  日期：——

  A simple, elegant and one-pot synthesis of 3,4-dihydro-4-phenylcoumarins, 4-phenylcoumarins and their derivatives by making use of solid support, montmorillonite K-10 clay in conjunction with microwave irradiation is described.

  描述了通过使用固相载体蒙脱石K-10粘土与微波辐射一起简单，优雅且一锅合成3,4-二氢-4-苯基香豆素，4-苯基香豆素及其衍生物。
• [EN] BENZOPYRONE DERIVATIVE AND USE THEREOF<br/>[FR] DÉRIVÉ DE LA BENZOPYRONE ET SON UTILISATION
  申请人：UNIV HUAZHONG SCIENCE TECH

  公开号：WO2012136147A1

  公开（公告）日：2012-10-11

  本发明属于药物化学领域，具体涉及一种苯并吡喃酮类衍生物及其应用。所述苯并吡喃酮类衍生物为具有式（I）结构的化合物或其药学上可接受的盐。经实验发现，该类化合物可用于预防或治疗神经精神类疾病。
• BENZOPYRONE DERIVATIVE AND USE THEREOF
  申请人：Huazhong University of Science and Technology

  公开号：EP2698369B1

  公开（公告）日：2017-02-01
• Synthesis and Biological Investigation of Coumarin Piperazine (Piperidine) Derivatives as Potential Multireceptor Atypical Antipsychotics
  作者：Yin Chen、Songlin Wang、Xiangqing Xu、Xin Liu、Minquan Yu、Song Zhao、Shicheng Liu、Yinli Qiu、Tan Zhang、Bi-Feng Liu、Guisen Zhang

  DOI：10.1021/jm400408r

  日期：2013.6.13

  The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine 132, D3, and serotonin S-HT1A and S-HT2A, receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]-isoxazol-3-yl)-piperidin-1-yl)butoxy)-4-methyl-8-chloro-2H- chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D-2 and D-3 and serotonin S-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for S-HT2C and H-1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.
• Ramana, M. M. V.; Kudav, N. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 339 - 341
  作者：Ramana, M. M. V.、Kudav, N. A.

  DOI：——

  日期：——