2-bromo-3,5-diphenylthiophene | 59156-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-bromo-3,5-diphenylthiophene
• 英文别名: 2-bromo-3,5-diphenyl-thiophene；2-Brom-3,5-diphenyl-thiophen
• CAS: 59156-22-8
• 化学式: C₁₆H₁₁BrS
• 分子量: 315.233
• InChiKey: YKTPNHVEYBMYLV-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  360.4±37.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-bromo-3,5-diphenylthiophene 在 正丁基锂 、 N-氟代双苯磺酰胺 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 2.5h， 以86%的产率得到2-fluoro-3,5-diphenylthiophene
  参考文献：
  名称：

  五元杂芳基溴化物的钯催化氟化深度评估

  摘要：

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

  DOI：

  10.1021/acs.organomet.5b00631
• 作为产物：
  描述：

  2,4-diphenylthiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以94%的产率得到2-bromo-3,5-diphenylthiophene
  参考文献：
  名称：

  五元杂芳基溴化物的钯催化氟化深度评估

  摘要：

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.

  DOI：

  10.1021/acs.organomet.5b00631

文献信息

• Heterocyclic Vinyl Ethers. XI. Electrophilic Substitution and Rearrangements of the 1,4-Dithiadiene Ring System¹
  作者：William E. Parham、Isadore Nicholson、Vincent J. Traynelis

  DOI：10.1021/ja01585a040

  日期：1956.2
• REINECKE, MANFRED G.;MAZZA, DARIO DEL, J. ORG. CHEM., 54,(1989) N, C. 2142-2146
  作者：REINECKE, MANFRED G.、MAZZA, DARIO DEL

  DOI：——

  日期：——
• US4174405A
  申请人：——

  公开号：US4174405A

  公开（公告）日：1979-11-13
• In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
  作者：Phillip J. Milner、Yang Yang、Stephen L. Buchwald

  DOI：10.1021/acs.organomet.5b00631

  日期：2015.10.12

  A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.