(E)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether | 729613-18-7

• 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: (E)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether
• 英文别名: (E)-(4-bromo-4-fluorobut-3-enyloxy)tert-butyldiphenylsilane；[(E)-4-bromo-4-fluorobut-3-enoxy]-tert-butyl-diphenylsilane
• CAS: 729613-18-7
• 化学式: C₂₀H₂₄BrFOSi
• 分子量: 407.398
• InChiKey: IEECMLBILAOFIE-CYVLTUHYSA-N

物化性质

• 沸点：
  402.7±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙醛 、 (E)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether 在 chromium dichloride 、 nickel dibromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以39%的产率得到(Z)-6-(tert-butyldiphenylsilanyloxy)-3-fluoro-1-methylhex-3-en-2-ol
  参考文献：
  名称：

  一种新型的非对映异构选择性合成的Nozaki-Hiyama-Kishi型反应的（Z）-氟代烯烃

  摘要：

  通过与相应的溴氟烯烃的Nozaki-Hiyama-Kishi型反应，对（Z）-2-氟代烯丙基醇进行了高度非对映选择性和简单的合成，从而可以轻松获得高度有趣的氟化合成子。

  DOI：

  10.1021/jo048093g
• 作为产物：
  描述：

  氟三溴甲烷 、 3-(tert-butyldiphenylsilyloxy)-1-propanal 在 diethylzinc 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.5h， 生成 (E)-4-bromo-4-fluoro-3-butenyl (1,1-dimethylethyl)(diphenyl)silyl ether
  参考文献：
  名称：

  A Facile and Mild Method for the Synthesis of Terminal Bromofluoroolefins via Diethylzinc-Promoted Wittig Reaction

  摘要：

  Synthesis of 1-bromo-1-fluoroolefins was achieved in good yields via a Wittig reaction promoted by diethylzinc, even with nonactivated aldehydes and ketones as starting materials.

  DOI：

  10.1021/ol049742d

文献信息

• Efficient Synthesis of Fluoroalkenes via Diethylzinc-Promoted Wittig Reaction
  作者：Philippe Jubault、Xavier Pannecoucke、Ludivine Zoute、Guillaume Dutheuil、Jean-Charles Quirion

  DOI：10.1055/s-2006-950208

  日期：2006.10

  The synthesis of α-fluoroacrylates and α-bromo-α-fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in the addition sequence was critical in order to obtain exclusively α-fluoroacrylates in good yields.

  α-氟丙烯酸酯和α-溴-α-氟烯烃的合成得到了非常好的产率，使用了醛和酮、三苯基磷、二乙基锌作为促进剂，以及乙基二溴氟乙酸酯或二溴氟甲烷。改变添加顺序对独占性获得α-氟丙烯酸酯的高产率至关重要。
• Chromium-mediated fluoroalkenylation reactions of 1,1-dibromo-1-fluoroalkane and 1-bromo-1-fluoroalkene derivatives
  作者：Akio Saito、Muga Nakagawa、Takeo Taguchi

  DOI：10.1016/j.jfluchem.2005.05.003

  日期：2005.8

  CrCl2- and NiCl2-mediated coupling reactions of E/Z mixture of 1-bromo-1-fluoroalkenes with aldehydes proceeded in a high stereoselectivity to give the corresponding (Z)-2-fluoroallylic alcohol derivatives. On the other hand, in the reaction of 1,1-dibromo-1-fluoroalkane with CrCl2, (Z)-fluoroalkene derivative was formed via alpha-elimination reaction of the chromium carbenoid intermediate accompanying the concomitant 1,2-shift of beta-hydrogen. (c) 2005 Elsevier B.V. All rights reserved.
• A Facile and Mild Method for the Synthesis of Terminal Bromofluoroolefins via Diethylzinc-Promoted Wittig Reaction
  作者：Xinsheng Lei、Guillaume Dutheuil、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1021/ol049742d

  日期：2004.6.1

  Synthesis of 1-bromo-1-fluoroolefins was achieved in good yields via a Wittig reaction promoted by diethylzinc, even with nonactivated aldehydes and ketones as starting materials.
• A Novel Diastereoselective Synthesis of (<i>Z</i>)-Fluoroalkenes via a Nozaki−Hiyama−Kishi-Type Reaction
  作者：Guillaume Dutheuil、Xinsheng Lei、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1021/jo048093g

  日期：2005.3.1

  A highly diastereoselective and straightforward synthesis for (Z)-2-fluoroallylic alcohols via a Nozaki−Hiyama−Kishi-type reaction with the corresponding bromofluoroolefins was developed, providing an easy access to highly interesting fluorinated synthons.

  通过与相应的溴氟烯烃的Nozaki-Hiyama-Kishi型反应，对（Z）-2-氟代烯丙基醇进行了高度非对映选择性和简单的合成，从而可以轻松获得高度有趣的氟化合成子。