7-甲氧基-8-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮 | 76474-93-6

• 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
• 中文名称: 7-甲氧基-8-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮
• 英文名称: 7-methoxy-8-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one
• 英文别名: 7-methoxy-8-[(3-methylbut-2-enyl)oxy]-2H-chromen-2-one；osthol；2H-1-Benzopyran-2-one, 7-methoxy-8-[(3-methyl-2-butenyl)oxy]-；7-methoxy-8-(3-methylbut-2-enoxy)chromen-2-one
• CAS: 76474-93-6
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: ACDXWKPFNJLKPD-UHFFFAOYSA-N

物化性质

• 密度：
  1.159

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-甲氧基-8-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮 在 硫酸 、 氢碘酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 瑞香素
  参考文献：
  名称：

  Coumarins in artemisia caruifolia

  摘要：

  DOI：

  10.1016/s0031-9422(00)82232-3
• 作为产物：
  描述：

  瑞香素 在 sodium hydride 、 potassium carbonate 作用下， 以 六甲基磷酰三胺 、 丙酮 为溶剂， 反应 1.5h， 生成 7-甲氧基-8-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  紫花苜蓿中两种香豆素的分离与合成

  摘要：

  摘要 从 Melampodium divaricatum 中分离出两种新的香豆素异构体，并通过光谱方法鉴定为 8-hydroxy-7-(3'-methyl-2'-butenyloxy)coumarin ( 1 ) 和 7-hydroxy-8-(3'-methyl -2'-丁烯氧基）香豆素（2）。每个异构体的区域选择性合成是通过两种不同的烷基化途径进行的，证实了它们的结构。

  DOI：

  10.1016/s0031-9422(00)85043-8

文献信息

• Revision of Structure of a New Coumarin Isolated from Artemisia carviforia WALL.
  作者：Takashi HARAYAMA、Keiko KATSUNO、Yoshitaka NISHITA、Masako FUJII

  DOI：10.1248/cpb.42.1550

  日期：——

  Four coumarins (1-4) were synthesized by routes shown in Charts 2-5, respectively. A proposed structure for a new coumarin isolated from Artemisia carviforia was incorrect, and the structure of coumarin should be represented by formula (3).

  四种香豆素（1-4）的合成路线分别如图 2-5 所示。从蒿属植物中分离出的一种新的香豆素的拟议结构不正确，香豆素的结构应由式（3）表示。
• Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins
  作者：Jabrane Azelmat、Serena Fiorito、Vito Alessandro Taddeo、Salvatore Genovese、Francesco Epifano、Daniel Grenier

  DOI：10.1016/j.phytol.2015.08.008

  日期：2015.9

  Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• Ahluwalia, Vinod Kumar; Khanna, Manjula; Singh, Rishi Pal, Gazzetta Chimica Italiana, 1981, vol. 111, # 11/12, p. 503 - 504
  作者：Ahluwalia, Vinod Kumar、Khanna, Manjula、Singh, Rishi Pal

  DOI：——

  日期：——
• Revision of the Structure of a New Coumarin Isolated from Artemisia carviforia Wall
  作者：Takashi Harayama、Keiko Katsuno、Yoshitaka Nishita、Masako Fujii、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.3987/com-00-s(i)40

  日期：——

  Four coumarins (1-4) were synthesized by the routes shown in Schemes 2-5, respectively. The previously proposed structure for a new coumarin isolated from Artemisia carviforia was incorrect; the structure of the coumarin is represented by formula(3).
• REISCH, J.;PODPETSCHNIG, ELKE, PHARMAZIE, 42,(1987) N 11, 744
  作者：REISCH, J.、PODPETSCHNIG, ELKE

  DOI：——

  日期：——