8-hydroxy-3-methyleneoct-4-en-2-yl benzoate | 1308659-54-2

• 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: 8-hydroxy-3-methyleneoct-4-en-2-yl benzoate
• 英文别名: [(Z)-8-hydroxy-3-methylideneoct-4-en-2-yl] benzoate
• CAS: 1308659-54-2
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: GLPWIBSYZKEOOB-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-3-methyleneoct-4-en-2-yl benzoate 在 mesitylene 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Ruthenium Hydride-Promoted Dienyl Isomerization: Access to Highly Substituted 1,3-Dienes

  摘要：

  Ruthenium hydrides were found to promote the positional isomerization of 1,3-dienes into more highly substituted 1,3-dienes in a stereoconvergent manner. The reaction can be conducted in one pot starting with terminal alkynes and alkenes by triggering decomposition of the Grubbs catalyst into a ruthenium hydride, which promotes the dienyl isomerization. The presence of an alcohol additive plays a helpful role in the reaction, significantly increasing the chemical yields. Mechanistic studies are consistent with hydrometalation of the geminally substituted alkene of the 1,3-diene and transit of the ruthenium atom across the diene framework via a pi-allylruthenium intermediate.

  DOI：

  10.1021/ja4011207
• 作为产物：
  描述：

  4-戊烯-1-醇 、 but-3-yn-2-yl benzoate 在 Hoveyda-Grubbs catalyst second generation 、 对苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 8-hydroxy-3-methyleneoct-4-en-2-yl benzoate 、 8-hydroxy-3-methyleneoct-4-en-2-yl benzoate
  参考文献：
  名称：

  烯烃和炔烃复分解交叉偶联中的原子经济

  摘要：

  在不饱和反应物的化学计量比接近1：1的情况下实现了交叉烯-炔的复分解反应。这允许使用更复杂的烯烃反应物而不牺牲过量的烯烃反应物。在烯烃中，探索了不同的烯丙基氧保护基。有趣的是，含有烯丙基羟基的烯烃被证明是最具反应性的。

  DOI：

  10.1021/ol200914j

文献信息

• Atom Economy in the Metathesis Cross-Coupling of Alkenes and Alkynes
  作者：Joseph R. Clark、Steven T. Diver

  DOI：10.1021/ol200914j

  日期：2011.6.3

  A cross ene-yne metathesis has been achieved at a nearly 1:1 stoichiometry of the unsaturated reactants. This allowed the use of more complex alkene reactants without sacrificing excess alkene reactant. In the alkene, different allylic oxygen protecting groups were explored. Interestingly, alkenes containing the allylic hydroxyl group proved to be the most reactive.

  在不饱和反应物的化学计量比接近1：1的情况下实现了交叉烯-炔的复分解反应。这允许使用更复杂的烯烃反应物而不牺牲过量的烯烃反应物。在烯烃中，探索了不同的烯丙基氧保护基。有趣的是，含有烯丙基羟基的烯烃被证明是最具反应性的。
• Removal of Ruthenium Using a Silica Gel Supported Reagent
  作者：Jonathan M. French、Caley A. Caras、Steven T. Diver

  DOI：10.1021/ol402339e

  日期：2013.11

  A solid-supported isocyanide ligand was developed to destroy active metathesis catalysts and to remove ruthenium byproducts from metathesis reactions. This method was able to significantly reduce the concentration of residual ruthenium from the organic products of several alkene and ene-yne metathesis reactions, under a variety of different conditions.
• Ruthenium Hydride-Promoted Dienyl Isomerization: Access to Highly Substituted 1,3-Dienes
  作者：Joseph R. Clark、Justin R. Griffiths、Steven T. Diver

  DOI：10.1021/ja4011207

  日期：2013.3.6

  Ruthenium hydrides were found to promote the positional isomerization of 1,3-dienes into more highly substituted 1,3-dienes in a stereoconvergent manner. The reaction can be conducted in one pot starting with terminal alkynes and alkenes by triggering decomposition of the Grubbs catalyst into a ruthenium hydride, which promotes the dienyl isomerization. The presence of an alcohol additive plays a helpful role in the reaction, significantly increasing the chemical yields. Mechanistic studies are consistent with hydrometalation of the geminally substituted alkene of the 1,3-diene and transit of the ruthenium atom across the diene framework via a pi-allylruthenium intermediate.