3-benzoyl-2H-chromene-2-thione | 1142124-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2H-chromene-2-thione
• 英文别名: Phenyl-(2-sulfanylidenechromen-3-yl)methanone
• CAS: 1142124-79-5
• 化学式: C₁₆H₁₀O₂S
• 分子量: 266.32
• InChiKey: ANDGZVFCWQGPOU-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  415.5±55.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  苯乙酮 在 indium(III) chloride 、 sodium hydride 、 尿素 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 3-benzoyl-2H-chromene-2-thione
  参考文献：
  名称：

  在无溶剂条件下通过InCl 3催化的β-氧二硫代酯环化反应制得高度官能化的2 H-苯二甲基-2-硫酮的简便方法

  摘要：

  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。

  DOI：

  10.1016/j.tet.2010.11.055

文献信息

• A catalyst-free route for the green and efficient synthesis of 2H-chromene-2-thiones in neutral ionic liquid
  作者：Rashmi Sharma、Anil Kumar

  DOI：10.1016/j.tetlet.2022.154271

  日期：2023.1

  Metal- and catalyst-free, environmentally benign and a facile synthetic route to 2H-chromene-2-thiones via cyclocondensation reaction of various salicylaldehydes and β-oxodithioesters by employing 1-butyl-3-methylimidazolium chloride, [Bmim]Cl as a neutral medium has been demonstrated for the first time.

  通过使用 1-丁基-3-甲基咪唑氯化物、[Bmim]Cl 作为中性溶剂，通过各种水杨醛和β-氧代二硫酯的环化缩合反应，实现2H-色烯-2-硫酮的无金属和无催化剂、环境友好且简便的合成途径介质首次被证明。
• 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。
• 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：——