2-((E)-4-Methoxy-4-phenyl-but-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane | 401513-63-1

• 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-((E)-4-Methoxy-4-phenyl-but-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• 英文别名: 2-[(E)-4-methoxy-4-phenylbut-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 401513-63-1
• 化学式: C₁₇H₂₅BO₃
• 分子量: 288.195
• InChiKey: STVMTUSTMGYJIN-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  碘苯 、 2-((E)-4-Methoxy-4-phenyl-but-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 在 氢氧化钾 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 以86%的产率得到1,4-diphenyl-1-methoxy-3-butene
  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 2-((E)-4-Methoxy-4-phenyl-but-1-enyl)-4,4,5,5-tetramethyl-[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.