2,3-dihydro-2-(4-methoxyphenyl)-4H-thiopyrano[2,3-b]pyridin-4-one | 1449491-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3-dihydro-2-(4-methoxyphenyl)-4H-thiopyrano[2,3-b]pyridin-4-one
• 英文别名: 2-(4-Methoxyphenyl)-2,3-dihydrothiopyrano[2,3-b]pyridin-4-one；2-(4-methoxyphenyl)-2,3-dihydrothiopyrano[2,3-b]pyridin-4-one
• CAS: 1449491-73-9
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: PRIFRDKUFVTFDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2E)-1-(2-chloropyridin-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-ol 在 manganese(IV) oxide 、 sodium hydrosulfide monohydrate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 2,3-dihydro-2-(4-methoxyphenyl)-4H-thiopyrano[2,3-b]pyridin-4-one
  参考文献：
  名称：

  A Convenient Synthesis of 2,3-Dihydro-4H-thiopyrano[2,3-b]-, -[2,3-c]-, or -[3,2-c]pyridin-4-ones by the Reaction of the Corresponding 1-(Chloropyridinyl)alk-2-en-1-ones with NaSH

  摘要：

  Abstract2,3‐Dihydro‐4H‐thiopyrano[2,3‐b]pyridin‐4‐ones 4 were prepared by a three‐step sequence from commercially available 2‐chloropyridine (1). Thus, successive treatment of 1 with iPr2NLi (LDA) and α,β‐unsaturated aldehydes gave 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ols 2, which were oxidized with MnO2 to 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ones 3. The reactions of 3 with NaSH⋅n H2O proceeded smoothly at 0° in DMF to provide the desired thiopyranopyridinones. Similarly, 2,3‐dihydro‐4H‐thiopyrano[2,3‐c]pyridin‐4‐ones 8 and 2,3‐dihydro‐4H‐thiopyrano[3,2‐c]pyridin‐4‐ones 12 were obtained starting from 3‐chloropyridine (5) and 4‐chloropyridine (9), respectively.

  DOI：

  10.1002/hlca.201200543

文献信息

• A Novel Synthesis of Heterocyclic Analogues of Thioflavanones from Haloheteroaromatic Carboxylic Acids
  作者：Jae In Lee

  DOI：10.5012/bkcs.2013.34.4.1253

  日期：2013.4.20

  Yb(OTf)3, at 200 o C. 7 The direct cyclocondensation of thiophenols and 3-methyl2-butenoic acid with methanesulfonic acid resulted in thiochroman-4-ones, with the corresponding disulfides and enol thioethers obtained as minor products. 8 Another thioflavanone synthesis involved intramolecular cyclization of 2'-mercaptochalcones, which are prepared by the base catalyzed condensation of 2'-benzylthioacetophenones

  硫代黄酮（2-苯基硫代铬曼-4-酮）是黄烷酮的硫代类似物，是一类有趣的杂环 1，因为它们的生物活性有时可以提高。我们最近研究了硫代黄烷酮在 MCF-7 人乳腺癌细胞系中的抗癌作用，发现它通过诱导细胞毒性较弱的细胞凋亡来抑制细胞增殖。2 硫代黄烷酮的 3-肉桂亚基衍生物对小鼠淋巴瘤细胞具有抗增殖作用 3，硫代色满 4-酮的 3-氯亚甲基衍生物具有抗真菌活性。4 Thiochroman-4-ones 通常通过 3-芳基巯基丙酸的 Friedel-Crafts 酰化合成，其通过将苯硫酚添加到 α,β 不饱和酯或用苯硫酚取代 3-溴（甲磺酰基）酯并随后水解制备，H2SO4 5 或多聚磷酸 6 以中等收率。3-芳基硫代丙酸的环化在 200 o C 下通过催化量的路易斯酸，例如 Bi(NTf2)3 或 Yb(OTf)3 进行。 7 苯硫酚和 3-甲基 2-丁烯酸与甲磺酸的直接缩合反应酸产生 thioc
• A Convenient Synthesis of 2,3-Dihydro-4<i>H</i>-thiopyrano[2,3-<i>b</i>]-, -[2,3-<i>c</i>]-, or -[3,2-<i>c</i>]pyridin-4-ones by the Reaction of the Corresponding 1-(Chloropyridinyl)alk-2-en-1-ones with NaSH
  作者：Kazuhiro Kobayashi、Ayumi Imaoka

  DOI：10.1002/hlca.201200543

  日期：2013.4

  Abstract2,3‐Dihydro‐4H‐thiopyrano[2,3‐b]pyridin‐4‐ones 4 were prepared by a three‐step sequence from commercially available 2‐chloropyridine (1). Thus, successive treatment of 1 with iPr2NLi (LDA) and α,β‐unsaturated aldehydes gave 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ols 2, which were oxidized with MnO2 to 1‐(2‐chloropyridin‐3‐yl)alk‐2‐en‐1‐ones 3. The reactions of 3 with NaSH⋅n H2O proceeded smoothly at 0° in DMF to provide the desired thiopyranopyridinones. Similarly, 2,3‐dihydro‐4H‐thiopyrano[2,3‐c]pyridin‐4‐ones 8 and 2,3‐dihydro‐4H‐thiopyrano[3,2‐c]pyridin‐4‐ones 12 were obtained starting from 3‐chloropyridine (5) and 4‐chloropyridine (9), respectively.