1-bromo-1,1-difluoro-3-(thiophen-3-yl)-2-propyne | 957109-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-bromo-1,1-difluoro-3-(thiophen-3-yl)-2-propyne
• CAS: 957109-11-4
• 化学式: C₇H₃BrF₂S
• 分子量: 237.068
• InChiKey: ZSDKPARIWRBMQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-bromo-1,1-difluoro-3-(thiophen-3-yl)-2-propyne 在 盐酸 、 四丁基氟化铵 、 碘 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 N-benzyl-2,2-difluoro-4-oxo-4-(thiophen-3-yl)butanamide
  参考文献：
  名称：

  Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams

  摘要：

  Functionalized gem-difluoro beta- and gamma-lactams were synthesized through a novel intramolecular hydroamination reaction of difluoropropargyl amides.beta-Lactams were obtained via a Baldwin disfavored 4-exo-digonal cyclization using palladium acetate as the catalyst, whereas gamma-lactams were produced under basic conditions. Acid hydration of gamma-lactams produced ketoamides or hemiaminals selectively.

  DOI：

  10.1021/ol701811z
• 作为产物：
  描述：

  3-乙炔基噻吩 在 正丁基锂 、 二溴二氟甲烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以95%的产率得到1-bromo-1,1-difluoro-3-(thiophen-3-yl)-2-propyne
  参考文献：
  名称：

  Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams

  摘要：

  Functionalized gem-difluoro beta- and gamma-lactams were synthesized through a novel intramolecular hydroamination reaction of difluoropropargyl amides.beta-Lactams were obtained via a Baldwin disfavored 4-exo-digonal cyclization using palladium acetate as the catalyst, whereas gamma-lactams were produced under basic conditions. Acid hydration of gamma-lactams produced ketoamides or hemiaminals selectively.

  DOI：

  10.1021/ol701811z

文献信息

• Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents
  作者：Guokai Liu、Satoru Mori、Xin Wang、Shun Noritake、Etsuko Tokunaga、Norio Shibata

  DOI：10.1039/c2nj40255f

  日期：——

  A series of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts 1 were readily synthesized by treatment of corresponding (bromodifluoromethyl)arylsulfoxides 2 and substituted benzenes 3 with triflic anhydride in moderate to good yields. The unsymmetrical sulfonium salts 1 with different aryl groups having electron-donating or electron-withdrawing substituents can be nicely constructed depending on the choice of 2 and 3. Bromodifluoromethylation of alkynes was evaluated by using the selected diarylsulfonium salts 1 to provide the desired bromodifluoromethylated alkynes in moderate to good yields.

  一系列不对称的 S-(溴二氟甲基)二芳基磺盐 1 通过将相应的 (溴二氟甲基)芳基亚砜 2 和取代苯 3 与三氟甲磺酸酐反应，迅速合成，产率为中等到良好。使用不同的电子给体或电子吸取取代基的芳基组的不对称磺盐 1 可以根据选择的 2 和 3 精巧构建。通过使用选定的二芳基磺盐 1 评估了炔烃的溴二氟甲基化反应，以中等到良好的产率提供所需的溴二氟甲基化炔烃。