3-Bromo-1-(3-chlorophenyl)but-3-en-1-ol | 1312591-68-6

• 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: 3-Bromo-1-(3-chlorophenyl)but-3-en-1-ol
• CAS: 1312591-68-6
• 化学式: C₁₀H₁₀BrClO
• 分子量: 261.546
• InChiKey: XPDNJWZBJLOUCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 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：

  3-Bromo-1-(3-chlorophenyl)but-3-en-1-ol 、 乙烯基溴化镁 在 甲基氯化镁 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 2.41h， 以87%的产率得到
  参考文献：
  名称：

  1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted Z-Alkene and Application to Prins Cyclization

  摘要：

  A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.

  DOI：

  10.1021/acs.orglett.5b00485
• 作为产物：
  描述：

  3-氯苯甲醛 、 2,3-二溴-1-丙烯 在 indium 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到3-Bromo-1-(3-chlorophenyl)but-3-en-1-ol
  参考文献：
  名称：

  An efficient indium-mediated 2-bromoallylation of aldehydes at low temperature in aqueous DMF

  摘要：

  An efficient synthesis of 2-bromohomoallylic alcohols was carried out via an indium-mediated Barbier-type 2-bromoallylation of aldehydes in moderate yields. The reaction was performed at low temperature (-20 degrees C) in aqueous DMF in order to minimize decomposition of 2-bromoallylindium reagent to allene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.053

文献信息

• An efficient indium-mediated 2-bromoallylation of aldehydes at low temperature in aqueous DMF
  作者：Yu Mi Kim、Sangku Lee、Sung Hwan Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.04.053

  日期：2011.6

  An efficient synthesis of 2-bromohomoallylic alcohols was carried out via an indium-mediated Barbier-type 2-bromoallylation of aldehydes in moderate yields. The reaction was performed at low temperature (-20 degrees C) in aqueous DMF in order to minimize decomposition of 2-bromoallylindium reagent to allene. (C) 2011 Elsevier Ltd. All rights reserved.
• 1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted <i>Z</i>-Alkene and Application to Prins Cyclization
  作者：Yongjin Xu、Zhiping Yin、Xinglong Lin、Zubao Gan、Yanyang He、Lu Gao、Zhenlei Song

  DOI：10.1021/acs.orglett.5b00485

  日期：2015.4.17

  A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.