ethylene glycol trans-1-(trimethylsilyl)-1-propane-3-boronate | 113999-42-1

• 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: ethylene glycol trans-1-(trimethylsilyl)-1-propane-3-boronate
• 英文别名: ethylene glycol trans-1-(trimethylsilyl)-1-propene-3-boronate；ethylene glycol (E)-1-(trimethylsilyl)-1-propene-3-boronate；ethylene (E)-γ-trimethylsilylallyl boronate；1,3,2-Dioxaborolane, 2-[(2E)-3-(trimethylsilyl)-2-propen-1-yl]-；[(E)-3-(1,3,2-dioxaborolan-2-yl)prop-1-enyl]-trimethylsilane
• CAS: 113999-42-1
• 化学式: C₈H₁₇BO₂Si
• 分子量: 184.118
• InChiKey: GYGVFCLOAGUWRB-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethylene glycol trans-1-(trimethylsilyl)-1-propane-3-boronate 在 calcium chloride 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 30.0h， 生成 (2R*,3R*)-(Z)-N-benzylidene-3-(trimethylsilyl)-4-penten-2-amine N-oxide
  参考文献：
  名称：

  Thermal and trimethylsilyl triflate catalyzed additions of allylsilanes to nitrones

  摘要：

  DOI：

  10.1021/jo00244a021

文献信息

• A Convergent Total Synthesis of Hemibrevetoxin B
  作者：Armen Zakarian、Alexandre Batch、Robert A. Holton

  DOI：10.1021/ja029225v

  日期：2003.7.1

  A convergent biomimetic synthesis of hemibrevetoxin B from d-glucal and d-arabinose utilizes an electrophile-promoted cascade anti-Baldwin cyclization of an epoxy alcohol. The epoxy alcohol arises from a palladium-catalyzed coupling of a highly functionalized organozinc compound and an alkenyl iodide, which serve as two chiral building blocks of similar size and complexity. This first successful implementation

  来自 d-葡糖和 d-阿拉伯糖的半短泡毒素 B 的会聚仿生合成利用了环氧醇的亲电子促进级联抗鲍德温环化。环氧醇产生于钯催化的高度官能化有机锌化合物和链烯基碘化物的偶联，它们作为两个具有相似大小和复杂性的手性结构单元。用于合成海洋多环醚毒素的级联环氧醇环化的首次成功实施需要 39 个步骤，总产率为 4%。
• Synthesis of the cannabisativine skeleton via an intramolecular allylsilane-nitrone cycloaddition
  作者：Peter G. M. Wuts、Yong Woon Jung

  DOI：10.1021/jo00261a001

  日期：1988.12
• The addition of .gamma.-(trimethylsilyl)allylboronates to imines
  作者：Peter G. M. Wuts、Yong Woon Jung

  DOI：10.1021/jo00001a067

  日期：1991.1

  The addition of gamma-(trimethylsilyl)allylboronates to imines is described and compared with the addition of simple allylboronates to imines. The addition of gamma-(trimethylsilyl)allylboronates to imines is found to be more efficient than the addition of simple allylboronates to imines. The stereoselectivity is dependant upon the nature of the imine; imines derived from aromatic aldehydes give anti products and imines derived from aliphatic aldehydes give syn products. Proof of stereochemistry was established by conversion of the anti and syn derivatives to their respective Z- and E-dienes by a methylation/E-2 elimination process. With alpha-alkoxy aldehydes the reaction proceeds with excellent selectivity giving the product of Felkin-Ahn addition.
• WUTS, PETER G. M.;JUNG, YONG-WOON, J. ORG. CHEM., 53,(1988) N6, C. 5989-5994
  作者：WUTS, PETER G. M.、JUNG, YONG-WOON

  DOI：——

  日期：——
• Thermal and trimethylsilyl triflate catalyzed additions of allylsilanes to nitrones
  作者：Peter G. M. Wuts、Yong Woon Jung

  DOI：10.1021/jo00244a021

  日期：1988.4