2-(3-(butylthiomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1260900-95-5

• 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: 2-(3-(butylthiomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[3-(Butylsulfanylmethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[3-(butylsulfanylmethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1260900-95-5
• 化学式: C₁₇H₂₇BO₂S
• 分子量: 306.277
• InChiKey: LMGDRNWBYBMSEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-(butylthiomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 2-溴-N,N-二甲基苯胺 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 0.17h， 以58%的产率得到3'-(butylthiomethyl)-N,N-dimethylbiphenyl-2-amine
  参考文献：
  名称：

  Microwave-Mediated Suzuki–Miyaura Cross-Couplings of Thioether- and ortho-Substituted Methylphenylboronic Acid Esters

  摘要：

  Hiterto unsuccessful cross-couplings of ortho-substituted or thioether-substituted methylphenylboronates have now been achieved, under microwave conditions, enabling the synthesis of a library of novel biaryls. Tetrakis(triphenylphosphine) palladium and various bases, for example, sodium carbonate or cesium fluoride, were found to mediate the crucial C-C bond-forming cross-coupling reaction.

  DOI：

  10.1055/s-0032-1317205
• 作为产物：
  描述：

  丁硫醇 、 (3-溴甲基苯基)硼酸频哪醇酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以88%的产率得到2-(3-(butylthiomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Microwave-Mediated Synthesis of an Arylboronate Library

  摘要：

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

  DOI：

  10.1021/co100011g