Lacinartin; 8-甲氧基-7-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮 | 73155-42-7

• 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: Lacinartin; 8-甲氧基-7-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮
• 中文别名: Lacinartin;8-甲氧基-7-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮
• 英文名称: Lacinartin
• 英文别名: 8-methoxy-7-(3-methylbut-2-en-1-yl)oxy-2H-1-benzopyran-2-one；8-methoxy-7-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one；8-methoxy-7-(3',3'-dimethylallyloxy)-coumarin；7-(3',3'-dimethylallyloxy)-8-methoxycoumarin；7-Isopentenyloxy-8-methoxycoumarin；8-methoxy-7-isopentenyloxycoumarin；8-methoxy-7-(3-methylbut-2-enoxy)chromen-2-one
• CAS: 73155-42-7
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: KBHJUIRMCYXTBK-UHFFFAOYSA-N

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：

  Lacinartin; 8-甲氧基-7-[(3-甲基-2-丁烯-1-基)氧基]-2H-1-苯并吡喃-2-酮 在 硫酸 作用下， 生成 7-羟基-8-甲氧基香豆素
  参考文献：
  名称：

  来自两个枞树种群的简单香豆素

  摘要：

  摘要 对枞树的两个集合的研究提供了七个简单的香豆素，其中三个是两个样品共有的。趋化单元

  DOI：

  10.1016/0031-9422(82)80171-4
• 作为产物：
  描述：

  瑞香素 在 碳酸氢钠 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 25.0h， 生成 Lacinartin; 8-甲氧基-7-[(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。
• Natural oxyprenylated coumarins are modulators of melanogenesis
  作者：Serena Fiorito、Francesco Epifano、Francesca Preziuso、Ivana Cacciatore、Antonio di Stefano、Vito Alessandro Taddeo、Philippe de Medina、Salvatore Genovese

  DOI：10.1016/j.ejmech.2018.04.051

  日期：2018.5

  Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor 13 and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Shimomura, Hiroko; Sashida, Yutaka; Ohshima, Yukio, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 347 - 348
  作者：Shimomura, Hiroko、Sashida, Yutaka、Ohshima, Yukio

  DOI：——

  日期：——
• 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).

表征谱图