(Z)-tert-butyldimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-3-en-1-yl)oxy)silane | 1338068-49-7

• 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: (Z)-tert-butyldimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-3-en-1-yl)oxy)silane
• 英文别名: (Z)-pinacolato (5-((tert-butyldimethylsilyl)oxy)-2-penten-1-yl)boronate
• CAS: 1338068-49-7
• 化学式: C₁₇H₃₅BO₃Si
• 分子量: 326.36
• InChiKey: WSATYNJTMNEIMS-KHPPLWFESA-N

物化性质

• 沸点：
  339.3±35.0 °C(predicted)
• 密度：
  0.90±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-tert-butyldimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-3-en-1-yl)oxy)silane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,2-双(二苯基膦基)苯 、 四丁基氟化铵 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides

  摘要：

  Palladium-catalyzed allyl-ally cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately modified conditions, this allyl allyl coupling strategy was found to apply to a range of substrates, generally occurring with high enantioselectivity (92:8 to >99:1 er) and good diastereoselection (4:1 to 14:1 dr).

  DOI：

  10.1021/ja2075967
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 bis(1,5-cyclooctadiene)nickel (0) 、 三环己基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (Z)-tert-butyldimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-3-en-1-yl)oxy)silane
  参考文献：
  名称：

  Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides

  摘要：

  Palladium-catalyzed allyl-ally cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately modified conditions, this allyl allyl coupling strategy was found to apply to a range of substrates, generally occurring with high enantioselectivity (92:8 to >99:1 er) and good diastereoselection (4:1 to 14:1 dr).

  DOI：

  10.1021/ja2075967

文献信息

• Cobalt‐Catalyzed Regio‐ and Stereoselective Hydroboration of Allenes
  作者：Can Li、Zheng Yang、Lei Wang、Yinlong Guo、Zheng Huang、Shengming Ma

  DOI：10.1002/anie.201915716

  日期：2020.4.6

  pincer-ligand-based cobalt-complex-catalyzed allene hydroboration affording Z-allylic boronates is described. The reaction demonstrates an excellent regio- as well as Z-stereoselectivity and a wide substrate scope that tolerates many functional groups. Based on solvent-assisted electrospray ionization mass spectrometry (SAESI-MS) studies, a rationale for the cobalt-catalyzed hydroboration involving the highly selective

  描述了一种有效的基于钳子配体的钴络合物催化的丙二烯硼氢化，得到Z-烯丙基硼酸酯。该反应显示出优异的区域选择性和Z-立体选择性，并具有宽泛的底物范围，可以耐受许多官能团。基于溶剂辅助电喷雾电离质谱（SAESI-MS）的研究，提出了钴催化硼氢化反应的基本原理，其中涉及将丙二烯高度选择性地插入Co-H键中以形成Z-烯丙基钴中间体。