1-((4-bromophenyl)sulfonyl)naphthalene | 881210-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((4-bromophenyl)sulfonyl)naphthalene
• 英文别名: 1-(4-Bromobenzene-1-sulfonyl)naphthalene；1-(4-bromophenyl)sulfonylnaphthalene
• CAS: 881210-51-1
• 化学式: C₁₆H₁₁BrO₂S
• 分子量: 347.232
• InChiKey: KQRNNKOIJBHUTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴苯 、 1-萘磺酰氯 在 iron(III) chloride 作用下， 以93%的产率得到1-((4-bromophenyl)sulfonyl)naphthalene
  参考文献：
  名称：

  Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A

  摘要：

  FeCl3 catalyzed an isomerization-free Friedel-Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer indole synthesis that effectively constructed both the indole core and side chain of the target molecule. The development of these methods enabled a rapid preparation of kilogram quantities of PHA-565272A.

  DOI：

  10.1021/op050208a

文献信息

• Selective Synthesis of <i>ortho-</i>Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions
  作者：Haibo Zhu、Yajing Shen、Daheng Wen、Zhang-Gao Le、Tao Tu

  DOI：10.1021/acs.orglett.8b03957

  日期：2019.2.15

  A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component

  已经建立了一步金（I）催化的化学选择方案以访问邻位取代的二芳基砜。ena啶咪唑基亚金络合物是焦亚硫酸氢钾（K 2 S 2 O 5）和二芳基碘鎓盐对硼酸进行芳基磺酰化的有效催化剂，即使以克为单位，也可得到（多）邻位取代的二芳基砜。与过渡金属催化的双组分偶联系统不同，二芳基碘鎓盐中的位阻芳基优先转移到体积较小的芳基上，以形成合成困难的靶标，包括具有药学重要性的靶标。
• Pd/NHC-catalyzed arylsulfonylation of boronic acids: A general and direct protocol to access diarylsulfones
  作者：Haibo Zhu、Liu Yang、Jia Meng、Zongbo Xie、Zhang-Gao Le、Tao Tu

  DOI：10.1016/j.tetlet.2020.152708

  日期：2021.1
• Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A
  作者：Thomas J. Fleck、Jiong Jack Chen、Cuong V. Lu、Kari J. Hanson

  DOI：10.1021/op050208a

  日期：2006.3.1

  FeCl3 catalyzed an isomerization-free Friedel-Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer indole synthesis that effectively constructed both the indole core and side chain of the target molecule. The development of these methods enabled a rapid preparation of kilogram quantities of PHA-565272A.