4,4,5,5-tetramethyl-2-[1-(4-methylphenyl)-5-phenylpentyl]-1,3,2-dioxaborolane | 1240790-17-3

• 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: 4,4,5,5-tetramethyl-2-[1-(4-methylphenyl)-5-phenylpentyl]-1,3,2-dioxaborolane
• 英文别名: 5-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(4-tolyl)pentane；4,4,5,5-Tetramethyl-2-[1-(4-methylphenyl)-5-phenylpentyl]-1,3,2-dioxaborolane
• CAS: 1240790-17-3
• 化学式: C₂₄H₃₃BO₂
• 分子量: 364.336
• InChiKey: VHKXIGPDLLHYCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4,4,5,5-tetramethyl-2-[1-(4-methylphenyl)-5-phenylpentyl]-1,3,2-dioxaborolane 在 双氧水 、 potassium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 1.0h， 生成 5-phenyl-1-(4-tolyl)pentan-1-ol
  参考文献：
  名称：

  Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp³-Carbon in 1,1-Diborylalkanes at Room Temperature

  摘要：

  The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.

  DOI：

  10.1021/ja105176v
• 作为产物：
  描述：

  对溴甲苯 、 2,2'-(5-phenylpentane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 在 二(三叔丁基膦)钯 KOH 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以72%的产率得到4,4,5,5-tetramethyl-2-[1-(4-methylphenyl)-5-phenylpentyl]-1,3,2-dioxaborolane
  参考文献：
  名称：

  Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp³-Carbon in 1,1-Diborylalkanes at Room Temperature

  摘要：

  The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.

  DOI：

  10.1021/ja105176v

文献信息

• Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling
  作者：Megan K. Armstrong、Gojko Lalic

  DOI：10.1021/jacs.9b02372

  日期：2019.4.17

  The differential dihydrofunctionalization of terminal alkynes is accomplished through the reductive three-component coupling of terminal alkynes, aryl halides, and pinacolborane. The transformation results in hydrofunctionalization of both π-bonds of an alkyne in a single reaction promoted by cooperative action of a copper/palladium catalyst system. The differential dihydrofunctionalization reaction

  末端炔烃的差异二氢官能化是通过末端炔烃、芳基卤化物和频哪醇硼烷的还原性三组分偶联来实现的。在铜/钯催化剂体系的协同作用下，该转化导致炔烃的两个 π 键在单一反应中发生加氢官能化。差异化二氢官能化反应具有优异的底物范围，可在酯类、腈类、卤代烷、环氧化物、缩醛、烯烃、芳基卤化物和甲硅烷基醚存在下完成。机理实验表明，该反应通过铜催化的硼氢化作用进行，然后是第二次氢化反应。由此产生的异双金属配合物是参与后续钯催化交叉偶联的关键中间体，
• Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp³-Carbon in 1,1-Diborylalkanes at Room Temperature
  作者：Kohei Endo、Takahiro Ohkubo、Munenao Hirokami、Takanori Shibata

  DOI：10.1021/ja105176v

  日期：2010.8.18

  The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.