7-chloro-2-phenyl-4H-thiochromen-4-one | 1207479-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 7-chloro-2-phenyl-4H-thiochromen-4-one
• 英文别名: 7-Chloro-2-phenylthiochromen-4-one
• CAS: 1207479-25-1
• 化学式: C₁₅H₉ClOS
• 分子量: 272.755
• InChiKey: NYNZIAQKEODUGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2,4-dichlorophenyl)-3-phenylprop-2-yn-1-one 在 sodium tetrahydroborate 、 sulfur 作用下， 反应 2.0h， 以83%的产率得到7-chloro-2-phenyl-4H-thiochromen-4-one
  参考文献：
  名称：

  Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen

  摘要：

  研发了一种替代绿色方法，用于合成硫和硒黄酮，通过2-氯苯基乙炔酮与NaHY（Y = S，Se）的环闭合反应。这些亲核硫和硒物种是在NaBH4的作用下在聚乙二醇-400（PEG-400）存在下生成的，用于还原元素硫或硒。这种反应的效率强烈依赖于PEG-400溶剂，起着类似冠醚的作用，与NaHY物种的钠原子形成络合物，使硫或硒亲核物质更活跃。合成方案在100°C的氩气氛下高效进行，使用含有烷基、芳基或乙烯基团的2-氯苯基乙炔酮以及硫和硒硫化物。通过这种高效简便的方法，经过2小时后得到了18种硫或硒黄酮，产率良好至优异。

  DOI：

  10.21577/0103-5053.20210051

文献信息

• Carbonylative Synthesis of Thiochromenones via Palladium-Catalyzed tert-Butyl Isocyanide Insertion
  作者：Yong-Ming Zhu、Fang-Ling Zhang、Zhen-Bang Chen、Kui Liu、Qing Yuan、Qing Jiang

  DOI：10.1055/s-0036-1591893

  日期：2018.3

  A flexible and efficient carbonylative synthesis of thiochromenones from the commercially available materials by utilizing tert-butyl isocyanide as carbonyl source has been developed. This methodology efficiently constructs thiochromenones in moderate to excellent yields with the advantages of wide range of substrates and being applicable to library synthesis.

  利用叔丁基异氰化物作为羰基源，从市售材料中灵活有效地羰基化合成硫代色酮。该方法以中等至优异的产率有效构建硫色酮，具有底物范围广的优点，适用于文库合成。
• Palladium-Catalyzed Carbonylative Four-Component Synthesis of Thiochromenones: The Advantages of a Reagent Capsule
  作者：Chaoren Shen、Anke Spannenberg、Xiao-Feng Wu

  DOI：10.1002/anie.201600953

  日期：2016.4.11

  reactions, especially those involving four or even more reagents, have been a long‐standing challenge because of the issues associated with balancing reactivity, selectivity, and compatibility. Herein, we demonstrate how the use of a reagent capsule provides straightforward access to synthetically valuable thiochromenone derivatives by a palladium‐catalyzed carbonylative four‐component reaction. To the

  由于涉及平衡反应性，选择性和相容性的问题，多组分反应（尤其是涉及四种甚至更多种试剂的反应）一直是一项长期挑战。本文中，我们证明了使用试剂胶囊如何通过钯催化的羰基化四组分反应直接获得具有合成价值的硫代色酮衍生物。据我们所知，这是使用胶囊防止催化剂中毒和多组分反应不良反应的第一个例子。
• Microwave-assisted three-component coupling-addition-S_NAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones
  作者：Benjamin Willy、Walter Frank、Thomas J. J. Müller

  DOI：10.1039/b917627f

  日期：——

  A whole family of annelated 4H-thiopyran-4-ones as the core structural unit was readily synthesized in good yields by a microwave-assisted coupling-addition-SNAr (CASNAR) sequence starting from readily available (het)aroyl chlorides, alkynes and sodium sulfide nonahydrate in a consecutive one-pot three-component reaction. All representatives display a pronounced halochromicity of the absorption bands

  微波辅助偶合-S N Ar（CASNAR）序列从容易获得的（杂）芳酰氯开始，以高收率容易地合成了全系列的4 H-硫代吡喃-4-酮作为核心结构单元。炔烃和九水合硫化钠在连续的一锅三组分反应中。所有代表在质子化时均显示出吸收带的明显的光致变色性。根据DFT计算，退火的4 H-硫吡喃-4-酮的电子基态具有相当大的两性离子特征。
• Transition metal free intramolecular S-arylation: one-pot synthesis of thiochromen-4-ones
  作者：T.A. Jenifer Vijay、Kebbahalli N. Nandeesh、Goravanahalli M. Raghavendra、Kanchugarakoppal S. Rangappa、Kempegowda Mantelingu

  DOI：10.1016/j.tetlet.2013.09.094

  日期：2013.11

  A convenient one-pot method for the synthesis of thiochromen-4-ones by the condensation of 2'-haloacetophenone and dithioesters at room temperature in the presence of NaH in DMF in moderate to good yields has been developed. The method involves unusual intramolecular S-arylation. The reaction is operationally facile, readily scalable and offers rapid entry into substituted chromene-4-ones. (C) 2013 Elsevier Ltd. All rights reserved.
• Denitrative Formal [5+1] Cycloaddition of 1‐(2‐Nitrophenyl)‐2‐Yn‐1‐Ones with Thioacetamide under Transition‐Metal‐Free Conditions: Synthesis of Thiochromen‐4‐Ones
  作者：Yao Xu、Wenjun Wang、Hui Fan、Xiaoming Liao、Zhuoran Yang、Lei Yu、Philip Wai Hong Chan、Xiaoxiang Zhang

  DOI：10.1002/ejoc.202400577

  日期：——

  A new strategy for thiochromen‐4‐one synthesis that relies on the denitrative formal [5 + 1] cycloaddition of 1‐(2‐nitrophenyl)‐2‐yn‐1‐ones with thioacetamide is described. Achieved under reaction conditions that did not require transition metal catalysis, nor the exclusion of air or moisture, the reaction is suggested to involve exploiting the propensity of thioacetamide to undergo hydrolysis under basic conditions. This is follows by addition of the ensuing sulfide anion to the 1,3‐alkynone and a nucleophilic aromatic substitution and denitrative rearomatization cascade to give the S‐heterocyclic product in yields of 41‐99%.