1-(4-hydroxy-3-methoxyphenyl)-2-phenylethan-1-one | 66476-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)-2-phenylethan-1-one
• 英文别名: 1-(4-hydroxy-3-methoxyphenyl)-2-phenyl-ethanone；benzyl 4-hydroxy-3-methoxyphenyl ketone；1-(4-hydroxy-3-methoxyphenyl)-2-phenyl-1-ethanone；4'-Hydroxy-3'-methoxy-2-phenylacetophenon；Benzyl vanillin；1-(4-hydroxy-3-methoxyphenyl)-2-phenylethanone
• CAS: 66476-02-6
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: ZBKGNSCMUWLTDL-UHFFFAOYSA-N

物化性质

• 熔点：
  108–110°C
• 沸点：
  422.7±30.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• 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：

  1-(4-hydroxy-3-methoxyphenyl)-2-phenylethan-1-one 在 吡啶 、 三氯化铝 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 生成 3-硝基-5-苯基乙酰基邻苯二酚
  参考文献：
  名称：

  Synthesis of 1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and Derivatives as Potent and Long-Acting Peripheral Inhibitors of Catechol-O-methyltransferase

  摘要：

  A homologous series of novel nitro-catechol structures (7a-7e) were synthesized and tested as inhibitors of the enzyme catechol-O-methyltransferase (COMT). Increasing chain length was found to have significant impact on both brain penetration and duration of COMT inhibition in the rat. Of this series, compound 7b (1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone) was found to exhibit the most potent and selective inhibition of peripheral COMT, with an inhibition profile more similar to entacapone 2 than tolcapone 1 (an equipotent peripheral and central inhibitor) but with much improved duration of action (7b, 70% inhibition and 2, 25% inhibition at 9 h after administration). The effects of structural modifications to 7b on COMT inhibitory profile were investigated, and it is concluded that the carbonyl group and preferably unsubstituted aromatic ring are essential features to maintain prolonged peripheral COMT inhibition. The introduction of the alpha-methylene group, the major structural difference between 7b and 1, would appear responsible for the observed enhancement in selectivity of peripheral COMT inhibition of 7b, which has more limited access to the brain than 1.

  DOI：

  10.1021/jm0109964
• 作为产物：
  描述：

  1-(4-benzyloxy-3-methoxyphenyl)-2-phenyl-ethanone 在 二氯甲烷 、 ice water 作用下， 以 二氯甲烷 、 氢溴酸 、 溶剂黄146 为溶剂， 反应 1.5h， 以to provide 1-(4-hydroxy-3-methoxyphenyl)-2-phenyl-1-ethanone as beige crystals, m.p. 107 to 108° C.的产率得到1-(4-hydroxy-3-methoxyphenyl)-2-phenylethan-1-one
  参考文献：
  名称：

  Substituted 2-phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them

  摘要：

  本文描述了化学式I的新化合物。这些化合物在治疗某些中枢和外周神经系统疾病方面具有潜在的有价值的药理特性，其中降低儿茶酚胺的O-甲基化可能具有治疗效益，例如帕金森病和帕金森综合症、胃肠道紊乱、水肿形成状态和高血压。

  公开号：

  US06512136B1

文献信息

• [EN] DUPA-INDENOISOQUINOLINE CONJUGATES<br/>[FR] CONJUGUÉS DUPA-INDÉNOISOQUINOLINE
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2015069766A1

  公开（公告）日：2015-05-14

  A targeting ligand-cytotoxic drug conjugate, for example, a DUPA-Indenoisoquinoline conjugate, is useful for treating cancers, e.g., prostate cancer.

  一种靶向配体-细胞毒性药物结合物，例如DUPA-Indenoisoquinoline结合物，可用于治疗癌症，例如前列腺癌。
• A Convenient One-Pot Completely Stereoselective Synthesis of <i>trans</i>-4-Hydroxystilbenes and Its Derivatives and X-Ray Structure of Its Precursor
  作者：Rakeshwar B. Chhor、Kunwar A. Singh、B. Nosse、Vishnu K. Tandon

  DOI：10.1081/scc-120021843

  日期：2003.1.8

  Abstract The synthesis of E-isomer of 4-Hydroxystilbene and its derivatives 3 by reductive elimination of the carbonyl function in 2-phenyl-1-(4-hydroxyphenyl)ethan-1-one and its derivatives 2 and the X-ray structure of 2a are described.

  摘要 通过还原消除 2-苯基-1-(4-羟基苯基)ethan-1-one 及其衍生物 2 中的羰基官能团合成 4-Hydroxystilbene 及其衍生物 3 的 E-异构体和其 X 射线结构2a 进行了描述。
• PRENYLATED HYDROXYSTILBENES
  申请人：The University of Sydney

  公开号：US20150307429A1

  公开（公告）日：2015-10-29

  Prenylated stilbene compounds and the use of such compounds in the treatment of diseases and medical disorders, for example cancer, skin ageing, inflammation, bacterial or fungal infection and immunosuppression.

  前醇基化仲苯烯化合物及其在治疗疾病和医学障碍方面的应用，例如癌症、皮肤老化、炎症、细菌或真菌感染和免疫抑制。
• Smoking compositions containing a vanillin-release beta-hydroxyester additive
  申请人：Philip Morris Products Inc.

  公开号：EP0461872A2

  公开（公告）日：1991-12-18

  This invention provides smoking compositions which contain a novel ß-hydroxyester flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as ethyl 3-hydroxy-3(4′-hydroxy-3′-methoxyphenyl)-2-phenylpropanoate pyrolyzes into vanillin and ethyl phenylacetate flavorants as volatile components of the cigarette smoke.

  本发明提供了含有新型ß-羟基酯香料释放添加剂的烟用组合物。 在吸食香烟的条件下，可燃填料和/或包装纸添加剂（如 3-羟基-3（4′-羟基-3′-甲氧基苯基）-2-苯基丙酸乙酯）会热解成香兰素和苯乙酸乙酯香料，作为香烟烟雾中的挥发性成分。
• Prenylated hydroxystilbenes
  申请人：Duke Colin Charles

  公开号：US10196335B2

  公开（公告）日：2019-02-05

  Prenylated stilbene compounds and the use of such compounds in the treatment of diseases and medical disorders, for example cancer, skin ageing, inflammation, bacterial or fungal infection and immunosuppression.

  异戊烯基二苯乙烯化合物，以及将此类化合物用于治疗疾病和医学紊乱，例如癌症、皮肤老化、炎症、细菌或真菌感染以及免疫抑制。