2-(3,4-dimethoxyphenyl)-4H-thiochromen-4-one | 35893-90-4

• 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: 2-(3,4-dimethoxyphenyl)-4H-thiochromen-4-one
• 英文别名: 2-(3',4'-Dimethoxyphenyl)-4h-1-benzothiopyran-4-one；2-(3,4-dimethoxyphenyl)thiochromen-4-one
• CAS: 35893-90-4
• 化学式: C₁₇H₁₄O₃S
• 分子量: 298.362
• InChiKey: LXEADOZRLZIUDW-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-[2-(4-methoxybenzylthio)phenyl]-2-(methylsulfinyl)ethanone 在 哌啶 、 甲酸 作用下， 以 甲苯 为溶剂， 反应 3.5h， 生成 2-(3,4-dimethoxyphenyl)-4H-thiochromen-4-one
  参考文献：
  名称：

  A new synthesis of thioflavones

  摘要：

  DOI：

  10.1016/s0040-4039(00)82060-2

文献信息

• A Novel Consecutive Three-Component Coupling-Addition-S_NAr (CASNAR) Synthesis of 4<i>H</i>-Thiochromen-4-ones
  作者：Thomas Müller、Benjamin Willy

  DOI：10.1055/s-0029-1216735

  日期：——

  4H-Thiochromen-4-ones and 4H-thiopyrano[2,3-b]pyridin-4-ones are readily synthesized in good yields by a consecutive one-pot, three-component coupling-addition-S N Ar (CASNAR) sequence starting from aroyl chlorides, alkynes, and sodium sulfide nonahydrate.

  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。
• A new preparation of substituted 4<i>H</i>-1-benzothiopyran-4-ones from c(α)<i>N</i>-benzoylhydrazones or c(α)<i>N</i>-carboalkoxyhydrazones and methyl thiosalicylate
  作者：Kristen L. French、April J. Angel、Angela R. Williams、Douglas R. Hurst、Charles F. Beam

  DOI：10.1002/jhet.5570350109

  日期：1998.1

  C(α)N-Benzoylhydrazones or C(α),N-carboalkoxyhydrazones were dilithiated with excess lithium diisopropylamide, and the dianion-type intermediates were condensed with lithiated methyl thiosalicylate, followed by cyclization/hydrolysis to substituted 4H-1-benzothiopyran-4-ones (thioflavones/thiochromones).

  用过量的二异丙基氨基锂将C（α）N-苯甲酰肼或C（α）N-羰基烷氧基hydr酮二锂化，将二价阴离子型中间体与锂化的硫代水杨酸甲酯缩合，然后环化/水解成取代的4 H -1-苯并噻吩并- 4-one（硫代黄酮/硫代色酮）。
• Copper-Catalyzed One-Pot Synthesis of 2-Arylthiochromenones: An in Situ Recycle of Waste Byproduct as Useful Reagent
  作者：Subramani Sangeetha、Govindasamy Sekar

  DOI：10.1021/acs.orglett.8b03508

  日期：2019.1.4

  Copper-catalyzed one-pot synthesis of various 2-arylthiochromenones is developed using xanthate as an odorless sulfur source from easily acquirable 2′-halochalcones. This methodology demonstrates that the cross-coupled product thiochromanone synthesized from 2′-halochalcones (upstream reaction) is oxidized to thiochromenone (downstream reaction) in the same pot using waste byproduct (KI) of the first

  使用黄原酸酯作为无味硫源，从容易获得的2'-卤代al烯中开发了铜催化的一锅合成各种2-芳基硫代色酮。该方法论证明了使用第一步的副产物（KI）作为强力氧化剂分子碘（I 2）。这种一锅法合成方法已进一步扩展为使用二甲基亚砜（DMSO）作为溶剂和亚甲基源来合成3,3'-亚甲基双硫黄酮。
• 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。
• Intermediates Formed in the Reaction of Benzenethiol or<i>t</i>-Butylthiobenzene with Ethyl Benzoylacetate in Polyphosphoric Acid
  作者：Hiroyuki Nakazumi、Shigeru Watanabe、Tohru Kitaguchi、Teijiro Kitao

  DOI：10.1246/bcsj.63.847

  日期：1990.3

  The reaction of benzenethiol with ethyl benzoylacetate in polyphosphoric acid (PPA) at low temperature gave mainly ethyl 3-phenyl-3,3-bis(phenylthio)propionate 8 as an intermediate in the synthesis of thioflavones, while that from t-butylthiobenzene under similar conditions gave ethyl 3-(phenylthio)cinnamate 7 as a major product and many by-products. The reaction constant for intramolecular cyclic

  苯硫醇与苯甲酰乙酸乙酯在多磷酸 (PPA) 中的低温反应主要得到 3-苯基-3,3-双(苯硫基)丙酸乙酯 8 作为合成硫黄酮的中间体，而在类似条件下由叔丁基硫苯合成条件得到 3-（苯硫基）肉桂酸乙酯 7 作为主要产物和许多副产物。使用哈米特取代基常数 σm 和 σm+，7 在 98% 硫酸中的分子内环缩合反应常数分别为 -0.46 和 -0.54。这表明 7 的苯硫醇部分的闭环位点处电子密度的增加促进了这种闭环反应。