3-benzoyl-8-methoxy-2H-chromene-2-thione | 1228956-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-8-methoxy-2H-chromene-2-thione
• 英文别名: (8-Methoxy-2-sulfanylidenechromen-3-yl)-phenylmethanone
• CAS: 1228956-75-9
• 化学式: C₁₇H₁₂O₃S
• 分子量: 296.346
• InChiKey: AUMLTFKCJHDMTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酮 在 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 3-benzoyl-8-methoxy-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

• 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：——
• Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters
  作者：Ganesh Chandra Nandi、Subhasis Samai、Maya Shankar Singh

  DOI：10.1021/jo101572c

  日期：2010.11.19

  An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)
• Microwave assisted synthesis of functionalized 2H-chromene-2-thiones and 1,2-dithiole-3-thiones from β-oxodithioesters: Characterization, in vitro cytotoxicity and in silico docking studies
  作者：Siji Thonivalappil Bhaskaran、Paulson Mathew

  DOI：10.1016/j.molstruc.2021.132071

  日期：2022.3

  β-Oxodithiocarboxylates condensed with salicylaldehydes in the presence of triethylamine under microwave irradiation to afford 2H-chromene-2-thiones in excellent yields. Microwave heating of a mixture of β-oxodithioesters and Lawesson's reagent (LR) under solvent-free conditions led to sulfurization of the β-oxodithioesters and subsequent cyclization to form 1,2-dithiole-3-thiones. The products were

  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。