7-chloro-2-(3,4-dimethoxyphenyl)-4H-thiochromen-4-one | 1173193-59-3

• 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-(3,4-dimethoxyphenyl)-4H-thiochromen-4-one
• 英文别名: 7-Chloro-2-(3,4-dimethoxyphenyl)thiochromen-4-one
• CAS: 1173193-59-3
• 化学式: C₁₇H₁₃ClO₃S
• 分子量: 332.807
• InChiKey: WVQPWRCXPQRLMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 sodiumsulfide nonahydrate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 7-chloro-2-(3,4-dimethoxyphenyl)-4H-thiochromen-4-one
  参考文献：
  名称：

  A Novel Consecutive Three-Component Coupling-Addition-S_NAr (CASNAR) Synthesis of 4H-Thiochromen-4-ones

  摘要：

  以酰氯、炔烃和硫化钠为起点，通过连续的一锅三组份偶联-加成-S N Ar (CASNAR) 顺序，4H-硫代色原-4-酮和 4H-硫代吡喃并[2,3-b]吡啶-4-酮很容易合成，而且产率很高。

  DOI：

  10.1055/s-0029-1216735

文献信息

• 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.