1-methoxy-4-(phenylsulfinyl)naphthalene | 1300714-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methoxy-4-(phenylsulfinyl)naphthalene
• 英文别名: 1-(Benzenesulfinyl)-4-methoxynaphthalene
• CAS: 1300714-29-7
• 化学式: C₁₇H₁₄O₂S
• 分子量: 282.363
• InChiKey: LCQKHQYLSUQALV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯二硫醚 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 49.0h， 生成 1-methoxy-4-(phenylsulfinyl)naphthalene
  参考文献：
  名称：

  Methyl Sulfinates as Electrophiles in Friedel–Crafts Reactions. Synthesis of Aryl Sulfoxides

  摘要：

  The Friedel-Crafts reaction of methyl alkyl-and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NFIR, NR2), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.

  DOI：

  10.1021/jo2006335

文献信息

• Dramatic Influence of Ionic Liquid and Ultrasound Irradiation on the Electrophilic Sulfinylation of Aromatic Compounds by Sulfinic Esters
  作者：Ngoc-Lan Nguyen、Hong-Thom Vo、Fritz Duus、Thi Luu

  DOI：10.3390/molecules22091458

  日期：——

  The sulfinylation reaction of aromatic and hetero-aromatic compounds with sulfinic esters as electrophiles has been investigated in different ionic liquids and by means of different Lewis acid salts in order to get moderate to good yields of asymmetrical sulfoxides. Mixtures of 1-butyl-3-methylimidazolium chloride and aluminum chloride were found to be the most efficient and recyclable reaction framework

  已经在不同的离子液体和不同的路易斯酸盐中研究了芳香族和杂芳香族化合物与亚磺酸酯作为亲电试剂的亚磺酰化反应，以获得中等至良好收率的不对称亚砜。发现 1-丁基-3-甲基咪唑氯化物和氯化铝的混合物是最有效和可回收的反应框架。超声处理似乎是最有用和最环保的活化方法，以提供比在更持久的常规搅拌条件下获得的产量更好或相当的亚砜。
• Methyl Sulfinates as Electrophiles in Friedel–Crafts Reactions. Synthesis of Aryl Sulfoxides
  作者：Francisco Yuste、Angélica Hernández Linares、Virginia M. Mastranzo、Benjamín Ortiz、Rubén Sánchez-Obregón、Alberto Fraile、José Luis García Ruano

  DOI：10.1021/jo2006335

  日期：2011.6.3

  The Friedel-Crafts reaction of methyl alkyl-and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NFIR, NR2), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.