2-allyl-2,3-butadien-1-ol | 1103182-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-allyl-2,3-butadien-1-ol
• 英文别名: 2-allyl-2,3-butadienol
• CAS: 1103182-08-6
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: KFWIULGORNWLQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-allyl-2,3-butadien-1-ol 在 吡啶 、 palladium diacetate 、 三溴化磷 、 potassium carbonate 作用下， 以 乙醚 、 丙酮 、 乙腈 为溶剂， 反应 16.8h， 生成 dimethyl 9-allyl-8-methylene-12-tosyl-12-azatricyclo[7.2.1.0(2,7)]dodeca-2,4,6-triene-11,11-dicarboxylate
  参考文献：
  名称：

  One-Pot Construction of Aza- or Oxa-Bridged Benzocycloheptanes from Readily Available 2,3-Allenyl Malonates or 2,3-Allenols ando-Iodobenzaldehyde or Imine

  摘要：

  A Pd(OAc)(2)-catalyzed reaction of 2,3-alkadienyl malonates or 2,3-allenols with o-lodobenzaldehyde or Its N-tosyl imine occurred smoothly In MeCN at 80 degrees C to form the oxa- or aza-bridged benzocycloheptane derivatives with Important biological potential. With the optically active 2,3-allenols, the absolute configurations of all the three chiral centers have been conveniently established.

  DOI：

  10.1021/ol102811x

文献信息

• Indium and zinc-mediated Barbier-type addition reaction of 2,3-allenals with allyl bromide: an efficient synthesis of 1,5,6-alkatrien-4-ols
  作者：Wangqing Kong、Chunling Fu、Shengming Ma

  DOI：10.1039/b812869c

  日期：——

  A zinc or indium-mediated Barbier-type addition reaction of 2,3-allenals with allyl bromide in a mixed medium of aqueous NH4Cl and THF (5 : 2) was developed to provide an efficient route to 1,5,6-alkatrien-4-ols, which is synthetically very useful. No 1,4-addition reaction was observed. Depending on the substrates, both indium and activated zinc afforded the 1,2-addition products in moderate to excellent yields: for terminal allenals, activated zinc was better while in other cases the yields with indium were relatively higher.

  开发了一种锌或铟催化的Barbier型加成反应，将2,3-烯丙醛与溴代烯丙基在氟化铵和THF的混合介质（5:2）中反应，提供了一条有效的合成1,5,6-烯三烯-4-醇的路径，这在合成上非常有用。未观察到1,4-加成反应。根据底物的不同，铟和活化锌均可在中等到优良的产率下提供1,2-加成产物：对于末端烯丙醛，活化锌表现更好，而在其他情况下，铟的产率相对较高。