3-(4-chlorobenzoyl)-2H-benzo[f]chromene-2-thione | 1263317-27-6

• 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-(4-chlorobenzoyl)-2H-benzo[f]chromene-2-thione
• 英文别名: 2-(4-chlorobenzoyl)benzo[f]chromene-3-thione；(4-chlorophenyl)(3-thioxo-3H-benzo[f]chromen-2-yl)methanone；(4-Chlorophenyl)-(3-sulfanylidenebenzo[f]chromen-2-yl)methanone；(4-chlorophenyl)-(3-sulfanylidenebenzo[f]chromen-2-yl)methanone
• CAS: 1263317-27-6
• 化学式: C₂₀H₁₁ClO₂S
• 分子量: 350.825
• InChiKey: JAAGPDJYVRMINF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 3-(4-chlorophenyl)-3-oxopropanedithioate 、 2-羟基-1-萘甲醛 在 copper(II) choride dihydrate 作用下， 反应 0.17h， 以89%的产率得到3-(4-chlorobenzoyl)-2H-benzo[f]chromene-2-thione
  参考文献：
  名称：

  Facile Synthesis of 3-Thioxo-3H-benzo[f]chromen-2-yl methanone and 3H-Benzo[f]chromene-3-one Under Solvent Free Condition

  摘要：

  在无溶剂条件下，在一定量的 $CuCl_2$ 催化剂存在下，通过缩合现成的 $\beta$ 二硫代氧化物和 S,S-缩醛与 2- 羟基-1-萘甲醛，开发出了一种简单、方便、高效和高产的香豆素组合库合成方法。

  DOI：

  10.5012/bkcs.2011.32.1.175

文献信息

• An expedient route to highly functionalized 2H-chromene-2-thiones via ring annulation of β-oxodithioesters catalyzed by InCl3 under solvent-free conditions
  作者：Rajiv Kumar Verma、Girijesh K. Verma、Keshav Raghuvanshi、Maya Shankar Singh

  DOI：10.1016/j.tet.2010.11.055

  日期：2011.1

  A convenient and one-pot synthesis of 3-aroyl/heteroaroyl-2H-chromene-2-thiones and benzo[f]2H-chromene-2-thiones has been developed by the condensation of β-oxodithioesters and salicylaldehydes/α-hydroxynaphthaldehydes in the presence of indium trichloride under solvent-free conditions. The reaction is operationally facile, readily scalable, and offers rapid entry into differentially substituted chromene-2-thione

  通过β-氧代二硫代酯与水杨醛/α-的缩合反应，开发出了一种方便的一锅合成3-芳酰基/杂芳酰基-2 H-亚甲基-2-硫酮和苯并[ f ] 2 H-亚甲基-2-硫酮的方法。在无溶剂条件下在三氯化铟存在下生成羟基萘醛。该反应操作简便，易于扩展，可快速进入差异取代的亚甲基-2-硫酮骨架。
• Synthesis of functionalized benzo[f]2H-chromenes and evaluation of their antimicrobial activities
  作者：Irom Harimala Chanu、Laishram Ronibala Devi、Nonibala Khumanthem、N. Irabanta Singh、Dalip Kumar、Okram Mukherjee Singh

  DOI：10.1134/s1068162017020054

  日期：2017.3

  Knoevenagel cyclocondensations of alpha-hydroxy naphthaldehyde with beta-oxodithioesters and ketene dithioacetals yielded 2H-benzo[f]chromene-2-thiones and 2H-benzo[f]chromen-2-ones, respectively, in high yields. The newly synthesized compounds were evaluated for antifungal and antibacterial activities. Among them, compounds (2-furyl)(3-thioxo-3H-benzo[f]chromen-2-yl)methanone and phenyl(3-oxo-3H-benzo[f]chromen-2-yl)methanone exhibited excellent antifungal activity against tested fungi Curvularia lunata and Fusarium moniliforme. The highest antibacterial activity against the tested bacteria Escherichia coli and Staphylococcus aureus was observed for (4-chlorophenyl)(3-oxo-3H-benzo[f]chromen-2-yl)methanone. The results of antimicrobial screening demonstrate that (2-furyl)(3-thioxo-3H-benzo[f]chromen-2-yl)methanone, phenyl(3-oxo-3H-benzo[f]chromen-2-yl)methanone, and (4-chlorophenyl)(3-oxo-3H-benzo[f]chromen-2-yl)methanone are promising as antimicrobial drugs.