methyl 4-(benzo[b]thiophene-3-yl)benzoate | 24344-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(benzo[b]thiophene-3-yl)benzoate
• 英文别名: methyl 4-(benzo[b]thiophen-3-yl)benzoate；Methyl 4-(1-benzothien-3-yl)benzoate；methyl 4-(1-benzothiophen-3-yl)benzoate
• CAS: 24344-74-9
• 化学式: C₁₆H₁₂O₂S
• 分子量: 268.336
• InChiKey: WDQLAIYZLZZZBO-UHFFFAOYSA-N

物化性质

• 沸点：
  435.3±38.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 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：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯甲酸甲酯 、 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 48.0h， 以24%的产率得到methyl 4-(benzo[b]thiophene-3-yl)benzoate
  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

• Room-Temperature Direct β-Arylation of Thiophenes and Benzo[<i>b</i>]thiophenes and Kinetic Evidence for a Heck-type Pathway
  作者：Chiara Colletto、Saidul Islam、Francisco Juliá-Hernández、Igor Larrosa

  DOI：10.1021/jacs.5b12242

  日期：2016.2.10

  The first example of a regioselective β-arylation of benzo[b]thiophenes and thiophenes at room temperature with aryl iodides as coupling partners is reported. This methodology stands out for its operational simplicity: no prefunctionalization of either starting material is required, the reaction is insensitive to air and moisture, and it proceeds at room temperature. The mild conditions afford wide

  报道了苯并[b]噻吩和噻吩在室温下以芳基碘作为偶联伙伴的区域选择性β-芳基化的第一个例子。这种方法因其操作简单而突出：不需要任何一种起始材料的预官能化，反应对空气和水分不敏感，并且在室温下进行。温和的条件提供了广泛的官能团耐受性，通常具有完全的区域选择性和高产率，从而形成高效的催化系统。包括 13C 和 2H KIE 在内的初步机理研究表明，该过程是通过噻吩双键上的协同碳钯化作用发生的，然后是碱基辅助的抗消除作用。
• Palladium-Catalyzed Phosphine-Free Direct C–H Arylation of Benzothiophenes and Benzofurans Involving MIDA Boronates
  作者：Mengmeng Huang、Yangjie Wu、Zhiwei Wang、Yabo Li、Beiqi Yan

  DOI：10.1055/s-0034-1379606

  日期：——

  With high regioselectivity, a series of benzoheterocyclic compounds were synthesized via palladiium-catalyzed phosphine-free C-H arylation of benzothiophenes/benzofurans with aryl MIDA boronates at 30-50 degrees C in moderate to excellent yields. MIDA boronates were used in C-H arylation of heterocycles for the first time. Under the optimal conditions, the benzothiophenes could be transformed into the beta-arylbenzothiophenes, and the benzofurans gave only alpha-aryl-substituted products.