ethyl 2-(1'-(4''-chlorophenyl)-1'(Z)-propen-2'-yl)-2-methyl-4-pentenoate | 1042096-81-0

• 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-(1'-(4''-chlorophenyl)-1'(Z)-propen-2'-yl)-2-methyl-4-pentenoate
• 英文别名: ethyl 2-allyl-4-(p-chlorophenyl)-2,3-dimethyl-3(Z)-butenoate
• CAS: 1042096-81-0
• 化学式: C₁₇H₂₁ClO₂
• 分子量: 292.806
• InChiKey: RGTMFKPPMAXESZ-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  乙酸烯丙酯 、 甲基氯化镁 、 ethyl 4-(p-chlorophenyl)-2-methyl-2,3-butadienoate 在 iron(III)-acetylacetonate 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以0.0497 g的产率得到ethyl 2-(1'-(4''-chlorophenyl)-1'(Z)-propen-2'-yl)-2-methyl-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

• Ferric Chloride Hexahydrate-Catalyzed Highly Regio- and Stereoselective Conjugate Addition Reaction of 2,3-Allenoates with Grignard Reagents: An Efficient Synthesis of β,γ-Alkenoates
  作者：Guobi Chai、Zhan Lu、Chunling Fu、Shengming Ma

  DOI：10.1002/adsc.200900091

  日期：2009.8

  Ferric chloride hexahydrate was shown to be an efficient catalyst for the conjugate addition of 2,3-allenoates with alkyl-, aryl-, or vinyl-Grignard reagents to synthesize polysubstituted β,γ-unsaturated alkenoates with high regio- and stereoselectivity. The in situ formed magnesium dienolate may readily react with different electrophilic reagents under different reaction conditions with or without

  六水合氯化铁被证明是2,3-烯丙基酸酯与烷基，芳基或乙烯基格氏试剂共轭加成以合成具有高区域和立体选择性的多取代的β，γ-不饱和烯酸酯的有效催化剂。在原位形成二烯醇镁可以容易地与具有或不具有催化剂不同的反应条件下不同亲电试剂反应以构建在酯基团的α位和碳-碳双键的stereocontrollable保留烯丙基季碳。