ethyl 2-methyl-5-phenyl-2-(1'-phenyl-1'(E)-propen-2'-yl)-4-pentenoate | 1042097-09-5

• 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: ethyl 2-methyl-5-phenyl-2-(1'-phenyl-1'(E)-propen-2'-yl)-4-pentenoate
• 英文别名: ethyl (E)-2-methyl-5-phenyl-2-[(E)-1-phenylprop-1-en-2-yl]pent-4-enoate
• CAS: 1042097-09-5
• 化学式: C₂₃H₂₆O₂
• 分子量: 334.458
• InChiKey: BGIMEUPMHNOBPW-FLXQFUDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 2-methyl-4-phenyl-2,3-butadienoate 、 甲基氯化镁 、 Cinnamyl bromide 在 iron(III)-acetylacetonate 、 copper(l) iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 以0.0323 g的产率得到ethyl 2-methyl-5-phenyl-2-(1'-phenyl-1'(E)-propen-2'-yl)-4-pentenoate
  参考文献：
  名称：

  Controllable Highly Stereoselective Reaction of in situ Generated Magnesium Dienolate Intermediates with Different Electrophiles

  摘要：

  In this paper, we have described an efficient controllable stereoselective a-acylation and -allylation reaction of the magnesium dienolate intermediates generated in situ from the Fe(III)-catalyzed reaction between 2,3-allenoates and Grignard reagents with different electrophiles to afford 2-acylated or allylated 3(Z)- or (E)-alkenoates depending on the nature of the electrophiles and reaction conditions. The distinct stereoselectivity may be caused by the isomerization of metallic Z-1,3-dienoate to E-1,3-dienoate via the intermediacy of anti-allylic MgCl and syn-metallic species.

  DOI：

  10.1021/ol8012815

文献信息

• Controllable Highly Stereoselective Reaction of <i>in situ</i> Generated Magnesium Dienolate Intermediates with Different Electrophiles
  作者：Zhan Lu、Guobi Chai、Xiaobing Zhang、Shengming Ma

  DOI：10.1021/ol8012815

  日期：2008.8.21

  In this paper, we have described an efficient controllable stereoselective a-acylation and -allylation reaction of the magnesium dienolate intermediates generated in situ from the Fe(III)-catalyzed reaction between 2,3-allenoates and Grignard reagents with different electrophiles to afford 2-acylated or allylated 3(Z)- or (E)-alkenoates depending on the nature of the electrophiles and reaction conditions. The distinct stereoselectivity may be caused by the isomerization of metallic Z-1,3-dienoate to E-1,3-dienoate via the intermediacy of anti-allylic MgCl and syn-metallic species.