(1-hydroxy-3,4-dihydronaphthalen-2-yl)(4-methoxyphenyl)-methanethione | 1432595-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1-hydroxy-3,4-dihydronaphthalen-2-yl)(4-methoxyphenyl)-methanethione
• CAS: 1432595-96-4
• 化学式: C₁₈H₁₆O₂S
• 分子量: 296.39
• InChiKey: SMMCQXUCIVJMMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1-hydroxy-3,4-dihydronaphthalen-2-yl)(4-methoxyphenyl)-methanethione 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 生成 4,5-Dihydro-2,3-diphenyl-2H-benzindazole
  参考文献：
  名称：

  Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity

  摘要：

  Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2-propenones (prepared in situ by base-induced alkylation of 1,3-monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in. refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.

  DOI：

  10.1021/jo400599e
• 作为产物：
  描述：

  4-甲氧基苯二硫代甲酸甲酯 、 3,4-二氢-1(2H)-萘酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到(1-hydroxy-3,4-dihydronaphthalen-2-yl)(4-methoxyphenyl)-methanethione
  参考文献：
  名称：

  1,3-双（杂）芳基单硫-1,3-二酮与叠氮化钠的反应：通过分子内N-O键形成区域选择性合成3,5-双（杂）芳基异恶唑

  摘要：

  据报道，在IBX催化剂存在下，一种有效的新的3,5-双（杂）芳基异恶唑合成涉及1,3-双（杂）芳基单硫-1,3-二酮与叠氮化钠的反应。该反应在室温下以高收率进行，适用于多种底物，包括5-甲基-3-芳基异恶唑的合成，5-甲基-3-芳基异恶唑是几种抗β-内酰胺酶的抗生素中存在的关键亚基。已经提出了形成异恶唑的可能机理。还通过使相应的1-（杂）芳基-1-（甲硫基）-4-（杂）亚芳基-丁-1-烯-反应而合成了一些5-苯乙烯基/芳基丁二烯基-3-（杂）芳基异恶唑。在较高温度下与叠氮化钠共3个。β-酮二硫酯与叠氮化钠的反应显示出可提供高产率的β-酮腈。

  DOI：

  10.1021/acs.joc.0c02216