3-acetyl-2H-chromene-2-thione | 1142124-91-1

• 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: 3-acetyl-2H-chromene-2-thione
• 英文别名: 1-(2-Sulfanylidenechromen-3-yl)ethanone
• CAS: 1142124-91-1
• 化学式: C₁₁H₈O₂S
• 分子量: 204.249
• InChiKey: GXPGEZYGGIOZIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  3-oxo-dithiobutyric acid methyl ester 、 水杨醛 在 三乙胺 作用下， 以 neat (no solvent) 为溶剂， 以92 %的产率得到3-acetyl-2H-chromene-2-thione
  参考文献：
  名称：

  微波辅助从 β-氧代二硫酯合成功能化的 2H-色烯-2-硫酮和 1,2-二硫醇-3-硫酮：表征、体外细胞毒性和计算机对接研究

  摘要：

  β-氧代二硫代羧酸盐在三乙胺存在下在微波辐射下与水杨醛缩合，以优异的产率得到 2 H-色烯-2-硫酮。在无溶剂条件下对 β-氧代二硫酯和劳森试剂 (LR) 的混合物进行微波加热，导致 β-氧代二硫酯硫化，随后环化形成 1,2-二硫醇-3-硫酮。产物通过NMR光谱和X-射线衍射技术表征。与之前的报道不同，这些反应在没有任何金属催化剂的情况下，在无溶剂条件下的短时间内发生。体内细胞毒性和计算机对接研究揭示了这些化合物作为抗癌剂的实用性。

  DOI：

  10.1016/j.molstruc.2021.132071

文献信息

• Application of β-Oxodithioesters in Domino and Multicomponent Reactions: Facile Route to Dihydropyrimidines and Coumarins
  作者：Okram Mukherjee Singh、Nepram Sushuma Devi

  DOI：10.1021/jo802585b

  日期：2009.4.17

  A facile route to hitherto unknown 5-methylmercaptothio-carbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones and substituted 2H-chromene-2-thiones has been developed. SnCl2 catalyzed cyclocondensation of beta-oxodithioesters with a variety of readily accessible aldehydes and urea affords the dihydropyrimidinones. The methodology involves the three-component Biginelli reaction. On the other hand, substituted salicylaldehyde and beta-oxodithioesters reacted under the same condition to afford the substituted 2H-chromene-2-thiones in high yields.
• Novel 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones: Synthesis and evaluation of their antioxidant activities
  作者：Okram Mukherjee Singh、Nepram Sushuma Devi、Dhanaraj Singh Thokchom、Gurumayum Jitendra Sharma

  DOI：10.1016/j.ejmech.2010.01.070

  日期：2010.6

  A facile, convenient and high yielding synthesis of a combinatorial library of 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones has been developed by the condensation of easily accessible beta-oxodithioesters and salicylaldehyde/substituted 2-hydroxybenzaldehydes under solvent-free conditions. The assessment of radical scavenging capacity of the compounds towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Five selected compounds were able to protect curcumin from the attack of sulfur free radical generated by radiolysis of glutathione (GSH). The newly synthesized compounds exhibited profound antioxidant activities Five of them rendered comparatively high antioxidant capacity.
• Devi, Nepram Sushuma; Singh, Thokchom Prasanta; Khumanthem, Nonibala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 9, p. 1224 - 1231
  作者：Devi, Nepram Sushuma、Singh, Thokchom Prasanta、Khumanthem, Nonibala、Singh, Okram Mukherjee

  DOI：——

  日期：——