3-(methylthio)-1H-naphtho[2,1-b]pyran-1-one | 173210-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-(methylthio)-1H-naphtho[2,1-b]pyran-1-one
• 英文别名: 3-(Methylthio)-1H-naphtho<2,1-b>pyran-1-one；3-(methylthio)-1H-benzo[f]chromen-1-one；3-Methylsulfanylbenzo[f]chromen-1-one；3-methylsulfanylbenzo[f]chromen-1-one
• CAS: 173210-17-8
• 化学式: C₁₄H₁₀O₂S
• 分子量: 242.298
• InChiKey: HWCLZVVJCMPEJI-UHFFFAOYSA-N

物化性质

• 沸点：
  401.0±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(methylthio)-1H-naphtho[2,1-b]pyran-1-one 在 碘 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以75%的产率得到2-iodo-3-(methylthio)-1H-benzo[f]chromen-1-one
  参考文献：
  名称：

  碘介导的 2-(甲硫基)-4 H -chromen-4-ones 的合成及其卤化反应研究

  摘要：

  开发了一种有效的碘介导方法，用于通过容易获得的 1-(2-苄氧基-芳基)-3,3-双-甲基硫烷基的分子内环化合成功能化的 2-(甲硫基)-4 H-色烯-4-酮-丙烯酮。合成的 chromen-4-ones 是各种化学反应的关键前体。从机制上讲，我们观察到碘介导的二硫代乙缩醛分子内环化是通过自由基途径进行的。3-Halo-2-(methylthio)-4 H -chromen-4-ones 是通过各种两锅或一锅卤化方法实现的。

  DOI：

  10.1021/acs.joc.1c00788
• 作为产物：
  描述：

  1-(2-(benzyloxy)naphthalen-1-yl)-3,3-bis(methylthio)prop-2-en-1-one 在 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以79%的产率得到3-(methylthio)-1H-naphtho[2,1-b]pyran-1-one
  参考文献：
  名称：

  碘介导的 2-(甲硫基)-4 H -chromen-4-ones 的合成及其卤化反应研究

  摘要：

  开发了一种有效的碘介导方法，用于通过容易获得的 1-(2-苄氧基-芳基)-3,3-双-甲基硫烷基的分子内环化合成功能化的 2-(甲硫基)-4 H-色烯-4-酮-丙烯酮。合成的 chromen-4-ones 是各种化学反应的关键前体。从机制上讲，我们观察到碘介导的二硫代乙缩醛分子内环化是通过自由基途径进行的。3-Halo-2-(methylthio)-4 H -chromen-4-ones 是通过各种两锅或一锅卤化方法实现的。

  DOI：

  10.1021/acs.joc.1c00788

文献信息

• Pyran derivatives
  作者：Mario Di Braccio、Giancarlo Grossi、Giorgio Roma、Cristina Marzano、Franca Baccichetti、Morena Simonato、Franco Bordin

  DOI：10.1016/s0014-827x(03)00160-5

  日期：2003.11

  The N-substituted tricyclic 2-aminochromone derivatives 1a, 2a, and 2b were obtained by treating the corresponding (methylthio) or (methylsulfinyl) derivatives 10, 11, or 12, respectively, with an excess of the proper amines. Compound 2c was synthesized through the reaction of 2-naphthol with the ethyl N,N-diphenylmalonamate/POCl(3) reagent 14. The N-substituted 4-aminocoumarin bicyclic and tricyclic derivatives 5-8 were prepared by treating the corresponding chloro derivatives with the excess suitable amines. Compounds 1, 2, 5-8 were tested in vitro for their antiproliferative activity (DNA synthesis inhibition in Ehrlich cells) and cytotoxicity (MTT test in HeLa cells). The inhibitory properties of three selected compounds (5c, 5e, 7c) on protein and RNA syntheses in Ehrlich cells were also evaluated. Among the 27 compounds tested, 10 4-aminocoumarin derivatives (5-8) and two 2-aminochromone derivatives (1a and 2a) showed an appreciable antiproliferative activity (IC(50) range: 1.74-13.8 microM), whereas only four compounds 5-8 exhibited a comparable cytotoxic activity (IC(50) range: 4.95-12.9 microM).
• Di Braccio; Roma; Leoncini, Il Farmaco, 1995, vol. 50, # 10, p. 703 - 711
  作者：Di Braccio、Roma、Leoncini、Poggi

  DOI：——

  日期：——
• Pyran derivatives XX. 2-Aminochromone benzo-fused derivatives with antiproliferative properties
  作者：Giorgio Roma、Mario Di Braccio、Giancarlo Grossi、Cristina Marzano、Morena Simonato、Franco Bordin

  DOI：10.1016/s0014-827x(98)00055-x

  日期：1998.7

  The N-substituted 2-aminochromones 1 and their benzo-fused derivatives 2-4 described herein were mostly prepared by treating the corresponding (methylthio) derivatives 10-13 with an excess of the proper amines. Only the morpholino derivatives 3d and 4c were obtained from the reaction of the ethyl 3-morpholino-3-oxopropanoate/POCl3 reagent with 1-naphthol or 1-methyl-2-naphthol, respectively. The amino derivatives 1-4, as well as their methylthio analogues 10-13, were tested in vitro for their inhibitory activity on the infectivity of T2 bacteriophage, on the macromolecular synthesis in Ehrlich cells and on the clonal growth capacity of HeLa cells. Several of the angular or linear aminonaphthopyranones 2 and 3 or 4, respectively, and the (methylthio) derivatives 10, 11 and 13 induced a significant inhibition of DNA synthesis, but usually a clearly lower inhibition of clonal growth. Only the Linear 2-amino-10-methyl-4H-naphtho [2,3-b]pyran-4-ones 4a and 4b significantly inhibited the clonal growth in HeLa cells and T2 bacteriophage infectivity, respectively. (C) 1998 Elsevier Science S.A. All rights reserved.
• Synthesis of functionalized flavones from 3-halo-2-(methylthio)-4H-chromen-4-ones
  作者：Amr Elagamy、Laila K. Elghoneimy、Reem K. Arafa、Ramendra Pratap

  DOI：10.1016/j.tetlet.2022.153882

  日期：2022.6

  A simple and efficient method for the synthesis of flavones was achieved by selective sulfide Liebeskind-Srogl cross-coupling reaction of 2-(methylthio)-4H-chromen-4-ones and 3-halo-2-(methylthio)-4H-chromen-4-ones with arylboronic acids. This method is the first example of employing Liebeskind-Srogl coupling for the synthesis of flavones. Various aryl groups can be directly installed to the chromone
• Iodine-Mediated Synthesis of 2-(Methylthio)-4<i>H</i>-chromen-4-ones and Study of Their Halogenation Reactions
  作者：Amr Elagamy、Ranjay Shaw、Chandan Shah、Ramendra Pratap

  DOI：10.1021/acs.joc.1c00788

  日期：2021.7.16

  2-(methylthio)-4H-chromen-4-ones by intramolecular cyclization of easily accessible 1-(2-benzyloxy-aryl)-3,3-bis-methylsulfanyl-propenones. The synthesized chromen-4-ones turn out to be a key precursor for various kinds of chemical reactions. Mechanistically, we observed that iodine-mediated intramolecular cyclization of ketene dithioacetal proceeded through a radical pathway. 3-Halo-2-(methylthio)-4H-chromen-4-ones

  开发了一种有效的碘介导方法，用于通过容易获得的 1-(2-苄氧基-芳基)-3,3-双-甲基硫烷基的分子内环化合成功能化的 2-(甲硫基)-4 H-色烯-4-酮-丙烯酮。合成的 chromen-4-ones 是各种化学反应的关键前体。从机制上讲，我们观察到碘介导的二硫代乙缩醛分子内环化是通过自由基途径进行的。3-Halo-2-(methylthio)-4 H -chromen-4-ones 是通过各种两锅或一锅卤化方法实现的。