tert-butyldimethylsilyldifluorobromopropyne | 745782-14-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: tert-butyldimethylsilyldifluorobromopropyne
• 英文别名: (3-bromo-3,3-difluoroprop-1-ynyl)-tert-butyl-dimethylsilane
• CAS: 745782-14-3
• 化学式: C₉H₁₅BrF₂Si
• 分子量: 269.204
• InChiKey: ZZZJRNQNGNFHLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyldifluorobromopropyne 在 indium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of a stable indium complex derived from γ-silyl-α,α-difluorobromopropyne: evaluation of experimental parameters

  摘要：

  Fluoroallenes, are potentially useful cyclization precursors because of the synergistic combination of fluorine's unique stereolectronic features and the rich chemistry of allenes. We have optimized the experimental conditions needed for the formation of a difluoropropargylindium complex 2. Sonication, lower reaction temperatures (5 degreesC), and dilute concentration of the starting material (0.15 M) are required to maximize production of this complex. Although the structure of this complex remains unknown, we have found that the nature of the alkyl substituents on the silyl group does not influence the formation of 2 but it does affects the allenyl 5 to propargyl 4 ratio. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.12.017
• 作为产物：
  描述：

  二溴二氟甲烷 、 (叔丁基二甲基)乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 9.0h， 以58%的产率得到tert-butyldimethylsilyldifluorobromopropyne
  参考文献：
  名称：

  Synthesis of a stable indium complex derived from γ-silyl-α,α-difluorobromopropyne: evaluation of experimental parameters

  摘要：

  Fluoroallenes, are potentially useful cyclization precursors because of the synergistic combination of fluorine's unique stereolectronic features and the rich chemistry of allenes. We have optimized the experimental conditions needed for the formation of a difluoropropargylindium complex 2. Sonication, lower reaction temperatures (5 degreesC), and dilute concentration of the starting material (0.15 M) are required to maximize production of this complex. Although the structure of this complex remains unknown, we have found that the nature of the alkyl substituents on the silyl group does not influence the formation of 2 but it does affects the allenyl 5 to propargyl 4 ratio. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.12.017

文献信息

• Nickel-Catalyzed Difluoroalkylation–Alkylation of Enamides
  作者：Chang Xu、Zhi-Fang Yang、Lun An、Xingang Zhang

  DOI：10.1021/acscatal.9b02488

  日期：2019.9.6

  Nickel-catalyzed carbodifunctionalization of alkenes is an efficient strategy for the construction of C–C bonds. However, applications of the strategy in dialkylation of alkenes remain underdeveloped due to the difficulties in suppressing competitive side reactions. We now describe a nickel-catalyzed tandem reaction by difluoroalkylation–alkylation of N-vinyl 2-pyrrolidinone with difluoroalkyl bromides

  镍催化烯烃的碳二官能化是构建C–C键的有效策略。然而，由于难以抑制竞争性副反应，该策略在烯烃二烷基化中的应用仍未开发。现在，我们通过N-乙烯基2-吡咯烷酮与二氟烷基溴化物和二烷基锌试剂的二氟烷基化-烷基化来描述镍催化的串联反应。该反应还可以扩展至N-乙烯基恶唑烷酮和N-乙烯基乙酰胺。该碳二官能化反应在温和的反应条件下顺利进行，具有良好的官能团耐受性，可轻松获得宝石-二氟烷基化的2-吡咯烷酮衍生物在药物化学中是令人关注的。