3-(4-methoxybenzoyl)-2H-chromene-2-thione | 1142124-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-methoxybenzoyl)-2H-chromene-2-thione
• 英文别名: (4-Methoxyphenyl)-(2-sulfanylidenechromen-3-yl)methanone
• CAS: 1142124-83-1
• 化学式: C₁₇H₁₂O₃S
• 分子量: 296.346
• InChiKey: VWBPIWIYZBARDU-UHFFFAOYSA-N

物化性质

• 熔点：
  187-189 °C
• 沸点：
  462.2±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

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：

  对甲氧基苯乙酮 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-(4-methoxybenzoyl)-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

• 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。
• 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：——
• 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。