3-(2,6-dimethylphenyl)benzo[b]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-(2,6-dimethylphenyl)benzo[b]thiophene
• 英文别名: 3-(2,6-Dimethylphenyl)-1-benzothiophene
• 化学式: C₁₆H₁₄S
• 分子量: 238.353
• InChiKey: GPHWBKRSSAKNJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2,6-dimethylphenyl)benzo[b]thiophene 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以38 %的产率得到2-(2,6-dimethylphenyl)benzo[b]thiophene
  参考文献：
  名称：

  Aryl Dance Reaction of Arylbenzoheteroles

  摘要：

  DOI：

  10.1021/acs.orglett.2c03442
• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 苯并噻吩 在 5%-palladium/activated carbon 、 caesium carbonate 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 以94%的产率得到3-(2,6-dimethylphenyl)benzo[b]thiophene
  参考文献：
  名称：

  Completely Regioselective Direct C–H Functionalization of Benzo[b]thiophenes Using a Simple Heterogeneous Catalyst

  摘要：

  The first completely selective C3 C-H arylation of benzo[b]thiophenes is reported, demonstrating previously unexploited reactivity of palladium. Benzo[b]thiophenes are coupled with readily available aryl chlorides using a ligand-free, dual catalytic system of heterogeneous Pd/C and CuCl. The reaction is operationally simple and insensitive to air and moisture, and it provides valuable products with complete selectivity. Significant investigations into the nature of the active catalytic species and mechanistic considerations are discussed.

  DOI：

  10.1021/ja403130g

文献信息

• A One-Pot Synthesis of Hindered 2,3-Diarylbenzo[<b><i>b</i></b>]thiophenes via Suzuki Reaction
  作者：André Samat、Arnault Heynderickx、Robert Guglielmetti

  DOI：10.1055/s-2002-19808

  日期：——

  Palladium-catalysed cross-coupling of 2,3-dibromobenzo[b]thiophene with phenylboronic acids bearing two ortho substi-tuents have been developed and used for the synthesis of sterically hindered 2,3-diarylbenzo[b]thiophenes.

  钯催化下的2,3-二溴苯并[b]噻吩与带有两个邻位取代基的苯硼酸的交叉偶联反应已得到开发，并用于合成空间位阻的2,3-二芳基苯并[b]噻吩。
• The Interrupted Pummerer Reaction in a Sulfoxide‐Catalyzed Oxidative Coupling of 2‐Naphthols
  作者：Zhen He、Alexander P. Pulis、David J. Procter

  DOI：10.1002/anie.201903492

  日期：2019.6.3

  A benzothiophene S‐oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2‐naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2‐naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S‐oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased

  通过H 2 O 2硫氧化原位生成的苯并噻吩S-氧化物催化剂介导2-萘酚的氧化偶联。催化过程的关键是使用不寻常的苯并噻吩S-氧化物中断的Pummerer反应，然后与第二个配偶偶合，捕获和转化2-萘酚配偶的反应性。新的催化歧管已在生物活性天然产物（±）-尼莫酮和（±）-异麦酮的合成中得到展示。尽管Pummerer反应被广泛使用，但它们在催化中的应用却很少，我们的方法代表了一种新的无金属C-C键形成的催化流形。
• Completely Regioselective Direct C–H Functionalization of Benzo[<i>b</i>]thiophenes Using a Simple Heterogeneous Catalyst
  作者：Dan-Tam D. Tang、Karl D. Collins、Frank Glorius

  DOI：10.1021/ja403130g

  日期：2013.5.22

  The first completely selective C3 C-H arylation of benzo[b]thiophenes is reported, demonstrating previously unexploited reactivity of palladium. Benzo[b]thiophenes are coupled with readily available aryl chlorides using a ligand-free, dual catalytic system of heterogeneous Pd/C and CuCl. The reaction is operationally simple and insensitive to air and moisture, and it provides valuable products with complete selectivity. Significant investigations into the nature of the active catalytic species and mechanistic considerations are discussed.
• Aryl Dance Reaction of Arylbenzoheteroles
  作者：Hikaru Nakahara、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.2c03442

  日期：2022.11.4