4-ethylhex-1-en-3-yl methyl carbonate | 1411630-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 4-ethylhex-1-en-3-yl methyl carbonate
• 英文别名: 4-Ethylhex-1-en-3-yl methyl carbonate
• CAS: 1411630-42-6
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: YVYGWHQOPQZRPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethylhex-1-en-3-yl methyl carbonate 、 2-溴-2-环己烯-1-酮 在 锰 、 氯化镍二甲氧基乙烷 、 新铜试剂 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 以51%的产率得到(E)-2-(4-ethylhex-2-en-1-yl)cyclohex-2-enone
  参考文献：
  名称：

  Selective Cross-Coupling of Organic Halides with Allylic Acetates

  摘要：

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

  DOI：

  10.1021/jo302086g
• 作为产物：
  描述：

  2-乙基丁醛 在 吡啶 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-ethylhex-1-en-3-yl methyl carbonate
  参考文献：
  名称：

  Selective Cross-Coupling of Organic Halides with Allylic Acetates

  摘要：

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

  DOI：

  10.1021/jo302086g

文献信息

• Rhodium-Catalyzed Dynamic Kinetic Asymmetric Allylation of Phenols and 2-Hydroxypyridines
  作者：Changkun Li、Bernhard Breit

  DOI：10.1002/chem.201603532

  日期：2016.10.4

  dynamic kinetic asymmetric allylation of different nucleophiles with racemic allylic carbonates has been developed. High regio‐ and enantioselectivities can be obtained under neutral conditions and, furthermore, the chemoselectivities can be controlled by different diphosphine ligands. (R,R)‐QuinoxP* leads to selective O‐allylation of phenols, whereas when embedding (S,S)‐DIOP as the ligand, 2‐naphthol

  受铑催化羧酸经济向丙二烯中添加羧酸的机理研究的启发，已开发出铑催化的不同亲核试剂与消旋烯丙基碳酸酯的动态动力学不对称烯丙基化反应。在中性条件下可以获得很高的区域选择性和对映选择性，此外，化学选择性可以通过不同的二膦配体来控制。（R，R）-QuinoxP *导致酚的选择性O-烯丙基化，而当嵌入（S，S）-DIOP作为配体时，2-萘酚首次以高对映选择性被邻-C-烯丙基化。为此，羟基吡啶可以通过Rh I /（S）-DTBM-Segphos的中间体与先前报道的对丙二烯的原子经济加成反应相同。
• Selective Cross-Coupling of Organic Halides with Allylic Acetates
  作者：Lukiana L. Anka-Lufford、Michael R. Prinsell、Daniel J. Weix

  DOI：10.1021/jo302086g

  日期：2012.11.16

  A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.