dibenzo[b,d]thiophen-4-yl methanesulfonate | 1314564-34-5

• 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: dibenzo[b,d]thiophen-4-yl methanesulfonate
• 英文别名: Dibenzothiophen-4-yl methanesulfonate
• CAS: 1314564-34-5
• 化学式: C₁₃H₁₀O₃S₂
• 分子量: 278.353
• InChiKey: KGKWEZNEYRNXIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium α-benzyloxymethyltrifluoroborate 、 dibenzo[b,d]thiophen-4-yl methanesulfonate 在 potassium phosphate 、 1,1'-bis(diisopropylphosphino)ferrocene 、 (2'-amino-[1,1'-biphenyl]-2-yl)palladium(II)chloride dimer 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以68%的产率得到4-((benzyloxy)methyl)dibenzo[b,d]thiophene
  参考文献：
  名称：

  Cross-Coupling of Mesylated Phenol Derivatives with Potassium Alkoxymethyltrifluoroborates

  摘要：

  Cross-coupling of mesylated phenol derivatives with various potassium alkoxymethyltrifluoroborates has been achieved. The corresponding aryl and heteroaryl alkoxymethyl compounds have been obtained with equal facility with both electron-rich and electron-poor substituents on the activated alcohol.

  DOI：

  10.1021/ol201469r
• 作为产物：
  描述：

  4-H氧基二苯并噻吩 、 甲基磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到dibenzo[b,d]thiophen-4-yl methanesulfonate
  参考文献：
  名称：

  Cross-Coupling of Mesylated Phenol Derivatives with Potassium Alkoxymethyltrifluoroborates

  摘要：

  Cross-coupling of mesylated phenol derivatives with various potassium alkoxymethyltrifluoroborates has been achieved. The corresponding aryl and heteroaryl alkoxymethyl compounds have been obtained with equal facility with both electron-rich and electron-poor substituents on the activated alcohol.

  DOI：

  10.1021/ol201469r

文献信息

• Cross-Coupling of Mesylated Phenol Derivatives with Potassium Cyclopropyltrifluoroborate
  作者：Gary A. Molander、Floriane Beaumard、Terren K. Niethamer

  DOI：10.1021/jo2015246

  日期：2011.10.7

  C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%.
• Suzuki–Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Mesylates
  作者：Gary A. Molander、Inji Shin

  DOI：10.1021/ol301221p

  日期：2012.6.15

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C-O activation of various mesylate derivatives to afford the corresponding products in moderate to good yields.