(4-bromo-2-methylbut-3-ynyloxy)-tert-butyldiphenylsilane | 686747-84-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4-bromo-2-methylbut-3-ynyloxy)-tert-butyldiphenylsilane
• 英文别名: (R)-((4-bromo-2-methylbut-3-yn-1-yl)oxy)(tert-butyl)diphenylsilane；[(2R)-4-bromo-2-methylbut-3-ynoxy]-tert-butyl-diphenylsilane
• CAS: 686747-84-2
• 化学式: C₂₁H₂₅BrOSi
• 分子量: 401.418
• InChiKey: CHYZRGNBAYTOHU-GOSISDBHSA-N

物化性质

• 沸点：
  417.9±51.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-bromo-2-methylbut-3-ynyloxy)-tert-butyldiphenylsilane 在 二溴硼烷 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Kerrigan, Michael H.; Jeon, Sang-Jin; Chen, Young K., Journal of the American Chemical Society, 2009, vol. 131, p. 8434 - 8445

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester 在 锂硼氢 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (4-bromo-2-methylbut-3-ynyloxy)-tert-butyldiphenylsilane
  参考文献：
  名称：

  Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods

  摘要：

  A new total synthesis of (-)-hennoxazole A is reported. The synthetic approach is based on the preparation of three similarly sized fragments resulting in a fast and convergent assembly of the natural product. The three key reactions of the synthesis include a highly stereoselective 1,5-anti aldol coupling, a gold-catalyzed alkoxycyclization reaction, and a stereocontrolled diene cross-metathesis. The synthesis involves integrated batch and flow chemistry methods leading to the natural product in 16 steps longest linear sequence and 2.8% overall yield.

  DOI：

  10.1055/s-0032-1318109

文献信息

• A One-Pot Multicomponent Coupling Reaction for the Stereocontrolled Synthesis of (<i>Z</i>)-Trisubstituted Allylic Alcohols
  作者：Young K. Chen、Patrick J. Walsh

  DOI：10.1021/ja0396145

  日期：2004.3.1

  In this Communication, we outline a new one-pot, multicomponent coupling reaction that allows easy access to (Z)-trisubstituted allylic alcohols. Our strategy is based on E to Z isomerization of the 1-bromo-1-dialkylvinylborane upon reaction with dialkylzinc reagents, and subsequent transmetalation to give (Z)-trisubstituted vinylzinc species. In situ trapping of the reactive vinylzinc intermediates with aldehydes furnished a series of (Z)-trisubstituted allylic alcohols. This method represents a viable alternative to the Still-Gennari modification of the HWE olefination reaction, and it has the advantage that it allows coupling of larger fragments.
• Kerrigan, Michael H.; Jeon, Sang-Jin; Chen, Young K., Journal of the American Chemical Society, 2009, vol. 131, p. 8434 - 8445
  作者：Kerrigan, Michael H.、Jeon, Sang-Jin、Chen, Young K.、Salvi, Luca、Carroll, Patrick J.、Walsh, Patrick J.

  DOI：——

  日期：——
• Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods
  作者：Steven Ley、Amadeo Fernández、Zebulon Levine、Marcus Baumann、Sarah Sulzer-Mossé、Christof Sparr、Sabrina Schläger、Albrecht Metzger、Ian Baxendale

  DOI：10.1055/s-0032-1318109

  日期：——

  A new total synthesis of (-)-hennoxazole A is reported. The synthetic approach is based on the preparation of three similarly sized fragments resulting in a fast and convergent assembly of the natural product. The three key reactions of the synthesis include a highly stereoselective 1,5-anti aldol coupling, a gold-catalyzed alkoxycyclization reaction, and a stereocontrolled diene cross-metathesis. The synthesis involves integrated batch and flow chemistry methods leading to the natural product in 16 steps longest linear sequence and 2.8% overall yield.