5,5-dimethyl-2-(4-pentylphenyl)-1,3,2-dioxaborinane | 934276-43-4

• 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: 5,5-dimethyl-2-(4-pentylphenyl)-1,3,2-dioxaborinane
• CAS: 934276-43-4
• 化学式: C₁₆H₂₅BO₂
• 分子量: 260.184
• InChiKey: TVLPIZWFOYIUJG-UHFFFAOYSA-N

物化性质

• 沸点：
  363.4±21.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-(4-pentylphenyl)-1,3,2-dioxaborinane 在 Rh/Al₂O₃ 、 水 、 氢气 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 40.0~60.0 ℃ 、354.66 kPa 条件下， 反应 33.0h， 生成 4-(1,1,2,2-tetrafluoro-2-(4-pentylcyclohexyl)ethyl)cyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Fluoroalkylcopper(I) Complexes Generated by the Carbocupration of Tetrafluoroethylene: Construction of a Tetrafluoroethylene-Bridging Structure

  摘要：

  We report a copper-mediated synthesis of a variety of 1,2-difunctionalized-1,1,2,2-tetrafluoroethylene derivatives via the carbocupration of tetrafluoroethylene. The key synthetic intermediates, 2-aryl-1,1,2,2-tetrafluoroethylcopper complexes, can be easily prepared, stored, and used as fluoroalkylation reagents. The molecular structure was unambiguously determined by X-ray crystallography and NMR analysis. We applied this method to the short-step synthesis of a liquid-crystalline compound bearing a tetrafluoroethylene-bridging structure.

  DOI：

  10.1021/ja5093776
• 作为产物：
  描述：

  4-戊基苯硼酸 、 2,2-二甲基-1,3-丙二醇 以 甲苯 为溶剂， 反应 10.0h， 以95%的产率得到5,5-dimethyl-2-(4-pentylphenyl)-1,3,2-dioxaborinane
  参考文献：
  名称：

  Fluoroalkylcopper(I) Complexes Generated by the Carbocupration of Tetrafluoroethylene: Construction of a Tetrafluoroethylene-Bridging Structure

  摘要：

  We report a copper-mediated synthesis of a variety of 1,2-difunctionalized-1,1,2,2-tetrafluoroethylene derivatives via the carbocupration of tetrafluoroethylene. The key synthetic intermediates, 2-aryl-1,1,2,2-tetrafluoroethylcopper complexes, can be easily prepared, stored, and used as fluoroalkylation reagents. The molecular structure was unambiguously determined by X-ray crystallography and NMR analysis. We applied this method to the short-step synthesis of a liquid-crystalline compound bearing a tetrafluoroethylene-bridging structure.

  DOI：

  10.1021/ja5093776

文献信息

• Divergent Synthesis of Fluoroalkyl Ketones through Controlling the Reactivity of Organoboronate Complexes
  作者：Gang Zhou、Zhuanzhuan Guo、Shanshan Liu、Xiao Shen

  DOI：10.1021/jacs.3c12150

  日期：2024.2.14

  silyl ethers as intermediates that react with various electrophiles to generate defluorinated ketones as the products. Moreover, in combination with peroxide, a 1,2-shift of fluoroalkyl group is favored over deboronative fluoride elimination to generate ketal intermediates, leading to the formation of ketones as the products. This transition-metal-free reaction is operationally simple, and aryl, alkenyl

  在此，我们报道了通过容易获得的有机硼酸酯和氟烷基酰基硅烷之间的可见光诱导反应来合成氟烷基酮。对原位生成的有机硼酸盐配合物的反应性进行选择性控制是实现不同转化的关键。在碱性条件下，有机硼酸酯配合物经历脱硼氟化物消除，导致形成烯醇甲硅烷基醚作为中间体，其与各种亲电试剂反应生成脱氟酮作为产物。此外，与过氧化物结合，氟烷基的1,2-位移比脱硼氟化物消除更有利于生成缩酮中间体，从而形成酮作为产物。这种无过渡金属的反应操作简单，芳基、烯基和烷基硼酸酯都是合适的底物。克级反应和生物活性分子（包括齐氟硅氧烷及其氟烷基类似物）的简便合成已经证明了其合成潜力。
• EP2036900
  申请人：——

  公开号：——

  公开（公告）日：——
• Fluoroalkylcopper(I) Complexes Generated by the Carbocupration of Tetrafluoroethylene: Construction of a Tetrafluoroethylene-Bridging Structure
  作者：Hiroki Saijo、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1021/ja5093776

  日期：2014.10.29

  We report a copper-mediated synthesis of a variety of 1,2-difunctionalized-1,1,2,2-tetrafluoroethylene derivatives via the carbocupration of tetrafluoroethylene. The key synthetic intermediates, 2-aryl-1,1,2,2-tetrafluoroethylcopper complexes, can be easily prepared, stored, and used as fluoroalkylation reagents. The molecular structure was unambiguously determined by X-ray crystallography and NMR analysis. We applied this method to the short-step synthesis of a liquid-crystalline compound bearing a tetrafluoroethylene-bridging structure.