2-methylthio-4H-4-chromenone | 173210-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methylthio-4H-4-chromenone
• 英文别名: 2-(methylthio)-4H-chromen-4-one；2-Methylsulfanylchromen-4-one
• CAS: 173210-15-6
• 化学式: C₁₀H₈O₂S
• 分子量: 192.238
• InChiKey: HIKJUNWWEHGYHM-UHFFFAOYSA-N

物化性质

• 沸点：
  297.4±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  2-methylthio-4H-4-chromenone 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-(4-methoxy-phenoxy)-chromen-4-one
  参考文献：
  名称：

  通过钯催化的分子内交叉脱氢偶联轻松合成香豆色酮

  摘要：

  已经实现了2-芳氧基取代的4-色酮的有效的无碱钯催化的分子内交叉脱氢偶联，以接近香豆酮色酮。可以容易地合成各种不同取代的香豆金属色酮（产率高达90％）。

  DOI：

  10.1016/j.tet.2021.132048
• 作为产物：
  描述：

  1-(2-(benzyloxy)phenyl)-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95%的产率得到2-methylthio-4H-4-chromenone
  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

• 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.
• Definition of the heterocyclic pharmacophore of bacterial methionyl tRNA synthetase inhibitors: potent antibacterially active non-quinolone analogues
  作者：Richard L Jarvest、Sula A Armstrong、John M Berge、Pamela Brown、John S Elder、Murray J Brown、Royston C.B Copley、Andrew K Forrest、Dieter W Hamprecht、Peter J O'Hanlon、Darren J Mitchell、Stephen Rittenhouse、David R Witty

  DOI：10.1016/j.bmcl.2004.05.070

  日期：2004.8

  Potent inhibitors of bacterial methionyl tRNA synthetase (MRS) have previously been reported. Through SAR of the quinolone moiety, the right hand side pharmacophore for MRS inhibition has now been defined as an NH-C-NH functionality in the context of a bicyclic heteroaromatic system. Potent antibacterial fused-pyrimidone and fused-imidazole analogues have been obtained and enantioselective activity demonstrated. Compound 46 demonstrated very good antibacterial activity against panels of antibiotic-resistant staphylococci and enterococci. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 2-Methylthio-4<i>H</i>-4-chromenones via Ketene Dithioacetal in the One-Pot Reaction
  作者：Ge Hyeong Lee、Chwang Siek Pak

  DOI：10.1080/00397919908086262

  日期：1999.7

  2-Methylthio-4H-4-chromenone which is key intermediate for the synthesis of 2-methylsulfonyl-4H-4-chromenone, equivalent to 2-halo-4H-4-chromenone, was very easily and efficiently synthesized from 2'-hydroxyacetophenone analogues via ketene dithioacetal in the one-pot reaction.
• Synthesis and Characterization of 2-Methylsulfonyl-4<i>H</i>-4-Chromenones
  作者：Ge Hyeong Lee、Sung Jin Ha、Chwang Siek Pak

  DOI：10.1080/00397919908086429

  日期：1999.8.1

  2-Methylsulfonyl-4H-4-chromenones which are important intermediate of 2-substituted 4H-4-chromenones, equivalent to 2-halo-4H-4-chromenone, were synthesized and first characterized.