(Z)-1-phenyl-4-bromobut-3-en-1-ol | 87921-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1-phenyl-4-bromobut-3-en-1-ol
• 英文别名: (Z)-4-bromo-1-phenylbut-3-en-1-ol
• CAS: 87921-58-2
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: FGTMUODJLFDHGZ-YWEYNIOJSA-N

物化性质

• 沸点：
  320.3±42.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙基溴化镁 、 (Z)-1-phenyl-4-bromobut-3-en-1-ol 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以86%的产率得到(3Z)-1-phenyl-3-hexen-1-ol
  参考文献：
  名称：

  Z-selective formation of substituted homoallyl alcohols

  摘要：

  DOI：

  10.1016/s0040-4039(00)88137-x
• 作为产物：
  描述：

  1-苯基-3-丁炔-1-醇 在 lithium aluminium tetrahydride 、 pyridine*bromine 作用下， 以 四氢呋喃 为溶剂， 反应 12.25h， 生成 3-溴-1-苯基-丁-3-烯-1-醇 、 (Z)-1-phenyl-4-bromobut-3-en-1-ol
  参考文献：
  名称：

  β-乙炔末端醇与氢化铝锂的水铝化

  摘要：

  在THF中用氢化锂铝将末端β-乙炔醇加氢，得到均烯丙基醇。用氘化水，碘或二溴化吡啶分解中间有机铝配合物已证明在三键处非区域选择性氢化物的侵蚀。

  DOI：

  10.1134/s1070363216020109

文献信息

• The Hydroboration of Propargyl Bromide. Simple One-Pot Three-Component Routes to (<i>Z</i>)-1-Bromoalk-1-en-4-ols and to <i>a</i><i>nti</i>-Homoallylic Alcohols
  作者：Marco Lombardo、Stefano Morganti、Claudio Trombini

  DOI：10.1021/jo005633a

  日期：2000.12.1

  toward either the synthesis of (Z)-1-bromoalk-1-en-4-ols 6 or anti-homoallylic alcohols 8. Two one-pot three-component processes were developed based on a sequence of four reactions; preparation of dialkylborane and hydroboration of propargyl bromide are the first steps. Then, quaternization with TEBABr may be carried out either in the presence of the aldehyde when (Z)-1-bromoalk-1-en-4-ols 6 are requested

  炔丙基溴与二烷基硼烷的氢硼化选择性地产生3-溴丙-1-烯-1-基二烷基硼烷13，其在与溴化物离子季铵化后经历一系列转化成许多烯丙基硼物种。通过实验条件的适当选择，能够捕获的反应中间体与醛和朝向的（Z）或者所述合成操纵过程-1- bromoalk -1-烯-4-醇6或抗高烯丙基醇8 。基于四个反应序列，开发了两个一锅三组分工艺；第一步是制备二烷基硼烷和炔丙基溴的硼氢化。然后，当需要（Z）-1-bromoalk-1-en-4-ols 6时，可以在醛存在下用TEBABr进行季铵化，
• A one-pot three-component route to anti-homoallylic alcohols based on the hydroborationof propargyl bromide
  作者：Lorenzo Gaddoni、Marco Lombardo、Claudio Trombini

  DOI：10.1016/s0040-4039(98)01615-3

  日期：1998.10

  (3-Bromoalken-1-yl)dialkylboranes, generated by hydroboration of propargyl bromide with dialkylboranes, smoothly rearranges to (E)-allylic boranes which can be trapped with aldehydes. The resulting one-pot three-component sequence represents a route to anti-homoallylic alcohols in fairly good yields. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  (3-溴丙烯-1-基)二烷基硼烷由炔丙基溴化物与二烷基硼烷发生水合反应生成，随后会顺利重排为(E)-烯丙基硼烷，这些产物可以被甲醛等醛类化合物捕获。所得到的三组分一锅反应代表了一条合成反式 Homoalllylic 酒精的路线，产率相当不错。 (C) 1998 由 Elsevier Science Ltd. 出版。所有权利保留。
• Diastereo- and Enantioselective Synthesis of <i>syn</i>-α-Vinylchlorohydrins and <i>cis</i>-Vinylepoxides
  作者：Shaojing Hu、Seetharaman Jayaraman、Allan C. Oehlschlager

  DOI：10.1021/jo960875p

  日期：1996.1.1

  A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF3 . OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de greater than or equal to 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-alpha a-halohydrins (de greater than or equal to 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-gamma-chloroallyl]BIpc(2) leads to chiral syn-alpha-chlorohydrins and cis-vinylepoxides in high de (greater than or equal to 90%) and ee(90-99%). Enantioselectivity of reactions of chiral (Z)-(gamma-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other alpha-or gamma-substituted allylboranes. The effects of proportion ofBF(3) . OEt(2) and the relative efficacies of LiNR(2) bases on diastereo- and enantioselectivity of the chloroallylation are reported.
• Julia, Marc; Verpeaux, Jean-Noel; Zahneisen, Thomas, Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 539 - 554
  作者：Julia, Marc、Verpeaux, Jean-Noel、Zahneisen, Thomas

  DOI：——

  日期：——
• Hoffmann, Reinhard W.; Landmann, Bernd, Chemische Berichte, 1986, vol. 119, # 3, p. 1039 - 1053
  作者：Hoffmann, Reinhard W.、Landmann, Bernd

  DOI：——

  日期：——