1,4-二甲氧基-2-((4-甲基苯基)硫代)萘 | 145146-93-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 1,4-二甲氧基-2-((4-甲基苯基)硫代)萘
• 英文名称: 1,4-Dimethoxy-2-<(4-methylphenyl)thio>naphthalene
• 英文别名: 1,4-Dimethoxy-2-(p-tolylthio)naphthalene；1,4-Dimethoxy-2-(4-methylphenyl)sulfanylnaphthalene
• CAS: 145146-93-6
• 化学式: C₁₉H₁₈O₂S
• 分子量: 310.417
• InChiKey: PRVNXWRWJWEIFP-UHFFFAOYSA-N

物化性质

• 沸点：
  468.1±40.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-二甲氧基-2-((4-甲基苯基)硫代)萘 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以96%的产率得到2-(p-tolylthio)naphthalene-1,4-dione
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036
• 作为产物：
  描述：

  1,4-二甲氧基萘 、 4-甲苯硫酚 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 以40%的产率得到1,4-二甲氧基-2-((4-甲基苯基)硫代)萘
  参考文献：
  名称：

  Novel and Direct Nucleophilic Sulfenylation and Thiocyanation of Phenol Ethers Using a Hypervalent Iodine(III) Reagent

  摘要：

  Novel and direct nucleophilic sulfenylation and thiocyanation of phenol ethers and related compounds (1) with the hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) have been developed. The reaction proceeded smoothly in 1,1,1,3,3,3-hexafluoro-2-propanol ((CF3)(2)-CHOH), a poorly nucleophilic and polar solvent. Various unsymmetrical diaryl sulfides and aryl thiocyanates, which could be applicable to the synthesis of various types of sulfur-containing aromatic compounds, were prepared in good yields. These reactions could be performed under mild conditions without heating or the use of strong Lewis acid catalysts.

  DOI：

  10.1021/jo00127a018

文献信息

• Novel and Direct Nucleophilic Sulfenylation and Thiocyanation of Phenol Ethers Using a Hypervalent Iodine(III) Reagent
  作者：Yasuyuki Kita、Takeshi Takada、Sachiko Mihara、Brendan A. Whelan、Hirofumi Tohma

  DOI：10.1021/jo00127a018

  日期：1995.11

  Novel and direct nucleophilic sulfenylation and thiocyanation of phenol ethers and related compounds (1) with the hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) have been developed. The reaction proceeded smoothly in 1,1,1,3,3,3-hexafluoro-2-propanol ((CF3)(2)-CHOH), a poorly nucleophilic and polar solvent. Various unsymmetrical diaryl sulfides and aryl thiocyanates, which could be applicable to the synthesis of various types of sulfur-containing aromatic compounds, were prepared in good yields. These reactions could be performed under mild conditions without heating or the use of strong Lewis acid catalysts.
• Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones
  作者：M. Carmen Carreno、Jose L. Garcia Ruano、Antonio Urbano

  DOI：10.1021/jo00051a036

  日期：1992.12

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.