(E)-tert-butyldimethyl-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-enyloxy)silane | 165059-46-1

• 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: (E)-tert-butyldimethyl-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-enyloxy)silane
• 英文别名: 1,3,2-Dioxaborolane, 2-[(2E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-propen-1-yl]-4,4,5,5-tetramethyl-；tert-butyl-dimethyl-[(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-enoxy]silane
• CAS: 165059-46-1
• 化学式: C₁₅H₃₁BO₃Si
• 分子量: 298.306
• InChiKey: IJRPNXDERDPLBT-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  苯甲醛 、 (E)-tert-butyldimethyl-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-enyloxy)silane 生成 (1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-but-3-en-1-ol 、 (1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-but-3-en-1-ol
  参考文献：
  名称：

  A stereoselective preparation of γ-alkoxyallylboronates via catalytic isomerization of pinacol [(E)-3-alkoxy-1-propenyl]boronates

  摘要：

  Isomerization of pinacol [(E)-3-alkoxy-1-propenyl]boronates to the corresponding gamma-alkoxy-allylboronates was catalyzed by ruthenium or iridium complexes, The [IrH2(thf)(2)(PPh(2)Me)(2)]PF6 complex was recognized to be a most efficient catalyst ro selectively provide (E)-gamma-alkoxyallylboronates under mild conditions.

  DOI：

  10.1016/0040-4039(95)00175-c
• 作为产物：
  描述：

  2-[(1E)-3-[[(叔丁基)二甲基硅烷基]氧基]-1-丙烯基]-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷 在 [(cod)Ir(Ph₂PMe)2]PF₆ pre-activated with H₂ 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到(E)-tert-butyldimethyl-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-enyloxy)silane
  参考文献：
  名称：

  Formal total synthesis of (−)-haouamine A

  摘要：

  本文介绍了一种基于催化作用的光活性吡咯里西啶生物碱(-1)的合成方法，该方法提供了先前用于构建这种细胞毒性海洋生物碱的六环化合物25。

  DOI：

  10.1039/b805295f

文献信息

• Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Oxygen-Substituted Allylboronates with Aryl/Vinyl (Pseudo)Halides
  作者：Jie Li、Xinhui Zhang、Yisen Yao、Yapei Gao、Wen Yang、Wanxiang Zhao

  DOI：10.1021/acs.joc.2c00634

  日期：2022.5.20

  cross-coupling reaction of oxygen atom-substituted allylboronates with aryl/vinyl bromides, iodides, and triflates has been developed. The present coupling reactions proceeded smoothly to provide a variety of allylic siloxanes with high efficiency and excellent regioselectivity. This protocol features broad substrate scope, excellent functional group tolerance, and easy gram-scale preparation, and offers an

  已经开发了氧原子取代的烯丙基硼酸酯与芳基/乙烯基溴化物、碘化物和三氟甲磺酸酯的高效钯催化 Suzuki-Miyaura 交叉偶联反应。本偶联反应顺利进行，提供了多种高效且区域选择性优异的烯丙基硅氧烷。该协议具有广泛的底物范围、出色的官能团耐受性和易于克级制备，并为烯丙醇及其衍生物的合成提供了一种替代方法。
• Formal total synthesis of (−)-haouamine A
  作者：Alois Fürstner、Jens Ackerstaff

  DOI：10.1039/b805295f

  日期：——

  A largely catalysis based approach to optically active haouamine A (−)-1 is presented, which provides the hexacyclic compound 25 previously used to construct this cytotoxic marine alkaloid.

  本文介绍了一种基于催化作用的光活性吡咯里西啶生物碱(-1)的合成方法，该方法提供了先前用于构建这种细胞毒性海洋生物碱的六环化合物25。
• A stereoselective preparation of γ-alkoxyallylboronates via catalytic isomerization of pinacol [(E)-3-alkoxy-1-propenyl]boronates
  作者：Tsukasa Moriya、Akira Suzuki、Norio Miyaura

  DOI：10.1016/0040-4039(95)00175-c

  日期：1995.3

  Isomerization of pinacol [(E)-3-alkoxy-1-propenyl]boronates to the corresponding gamma-alkoxy-allylboronates was catalyzed by ruthenium or iridium complexes, The [IrH2(thf)(2)(PPh(2)Me)(2)]PF6 complex was recognized to be a most efficient catalyst ro selectively provide (E)-gamma-alkoxyallylboronates under mild conditions.