4-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one | 1159919-08-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 4-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one
• 英文别名: 4-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one
• CAS: 1159919-08-0
• 化学式: C₁₂H₂₃BO₃
• 分子量: 226.124
• InChiKey: NIHPPPXMQHDOOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  264.1±23.0 °C(predicted)
• 密度：
  0.93±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 、 联硼酸频那醇酯 在 sodium t-butanolate 、 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以92%的产率得到4-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentan-2-one
  参考文献：
  名称：

  Lee, Kang-sang; Zhugralin, Adil R.; Hoveyda, Amir H., Journal of the American Chemical Society, 2009, vol. 131, p. 7253 - 7255

  摘要：

  DOI：

文献信息

• Structure and Reactivity of a Preactivated sp²–sp³ Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds
  作者：Ming Gao、Steven B. Thorpe、Christian Kleeberg、Carla Slebodnick、Todd B. Marder、Webster L. Santos

  DOI：10.1021/jo2003488

  日期：2011.5.20

  A novel sp(2)-sp(3) diboron reagent has been developed for the copper-catalyzed beta-boration of alpha,beta-unsaturated conjugated compounds. The reaction proceeds under mild conditions with various substrates, i.e., alpha,beta-unsaturated esters, ketones, nitriles, ynones, amides, and aldehydes, in the absence of additives such as phosphine and sodium tert-butoxide to provide beta-borylhomoenolates in good to excellent yields. The presence of an sp(3)-hybridized boron center, un-ambigously confirmed by X-ray crystallography, sufficiently activates the unsymmetrical pinacolato diisopropanolaminato diboron (PDIPA diboron, 2) to transfer the sp(2)-hybridized boron moiety chemoselectively. These observations suggest that the activation of one of the boron atoms is an essential step in the Cu-catalyzed beta-boration catalytic cycle.