4,4,5,5-tetramethyl-2-[(E)-4-phenyl-4-phenylmethoxybut-1-enyl]-1,3,2-dioxaborolane | 401513-67-5

• 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: 4,4,5,5-tetramethyl-2-[(E)-4-phenyl-4-phenylmethoxybut-1-enyl]-1,3,2-dioxaborolane
• CAS: 401513-67-5
• 化学式: C₂₃H₂₉BO₃
• 分子量: 364.292
• InChiKey: GSZVKUDZTFEFGC-GZTJUZNOSA-N

物化性质

• 沸点：
  438.9±55.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-2-[(E)-4-phenyl-4-phenylmethoxybut-1-enyl]-1,3,2-dioxaborolane 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(E)-1-Phenyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-but-3-en-1-ol
  参考文献：
  名称：

  1-Silyl-1-boryl-2-alkenes: Reagents for Stereodivergent Allylation Leading to 4-Oxy-(E)-1-alkenylboronates and 4-Oxy-(Z)-1-alkenylsilanes

  摘要：

  Silylboryl reagents for organic synthesis: 1-silyl-1-boryl-2-alkenes (2) were prepared efficiently by gem-silylborylation of α-chloroallyllithium compounds from (dimethylphenylsilyl)(pinacolato)borane (1; see scheme, LDA=lithium diisopropylamide) and were demonstrated to allylate acetals and aldehydes in the presence of a Lewis acid to produce (E)-4-alkoxy-alkenylboronates. Heating the reagents with aldehydes in the absence of Lewis acid afforded (Z)-4-hydroxy-alkenylsilanes stereospecifically.

  DOI：

  10.1002/1521-3773(20011119)40:22<4283::aid-anie4283>3.0.co;2-3
• 作为产物：
  描述：

  (二甲基苯硅烷基)硼酸频那醇酯 在 四氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 4,4,5,5-tetramethyl-2-[(E)-4-phenyl-4-phenylmethoxybut-1-enyl]-1,3,2-dioxaborolane
  参考文献：
  名称：

  1-Silyl-1-boryl-2-alkenes: Reagents for Stereodivergent Allylation Leading to 4-Oxy-(E)-1-alkenylboronates and 4-Oxy-(Z)-1-alkenylsilanes

  摘要：

  Silylboryl reagents for organic synthesis: 1-silyl-1-boryl-2-alkenes (2) were prepared efficiently by gem-silylborylation of α-chloroallyllithium compounds from (dimethylphenylsilyl)(pinacolato)borane (1; see scheme, LDA=lithium diisopropylamide) and were demonstrated to allylate acetals and aldehydes in the presence of a Lewis acid to produce (E)-4-alkoxy-alkenylboronates. Heating the reagents with aldehydes in the absence of Lewis acid afforded (Z)-4-hydroxy-alkenylsilanes stereospecifically.

  DOI：

  10.1002/1521-3773(20011119)40:22<4283::aid-anie4283>3.0.co;2-3

文献信息

• 1-Silyl-1-boryl-2-alkenes: Reagents for Stereodivergent Allylation Leading to 4-Oxy-(E)-1-alkenylboronates and 4-Oxy-(Z)-1-alkenylsilanes
  作者：Masaki Shimizu、Hirotaka Kitagawa、Takuya Kurahashi、Tamejiro Hiyama

  DOI：10.1002/1521-3773(20011119)40:22<4283::aid-anie4283>3.0.co;2-3

  日期：2001.11.19

  Silylboryl reagents for organic synthesis: 1-silyl-1-boryl-2-alkenes (2) were prepared efficiently by gem-silylborylation of α-chloroallyllithium compounds from (dimethylphenylsilyl)(pinacolato)borane (1; see scheme, LDA=lithium diisopropylamide) and were demonstrated to allylate acetals and aldehydes in the presence of a Lewis acid to produce (E)-4-alkoxy-alkenylboronates. Heating the reagents with aldehydes in the absence of Lewis acid afforded (Z)-4-hydroxy-alkenylsilanes stereospecifically.