(E)-methyl 3-(4-formylphenyl)-2-methylacrylate | 161772-82-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 3-(4-formylphenyl)-2-methylacrylate
• 英文别名: methyl (E)-3-(4-formylphenyl)-2-methylprop-2-enoate
• CAS: 161772-82-3
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: GRKHANFSKKSUQV-VQHVLOKHSA-N

物化性质

• 熔点：
  41.2-42.0 °C
• 沸点：
  339.5±25.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(4-formylphenyl)-2-methylacrylate 在 lithium aluminium tetrahydride 、 高氯酸 作用下， 以 乙醚 为溶剂， 生成 (E)-3-(4-Dimethoxymethyl-phenyl)-2-methyl-prop-2-en-1-ol
  参考文献：
  名称：

  A novel approach to the synthesis of benzoic and cinnamic acid derivatives with nor-isoprenoid substituents

  摘要：

  A novel strategy for the synthesis of 4-(nor-polyprenyl)-substituted benzoic acids and their esters of the general formula 1 as well as their vinylogs of the type 2, based on the use of terephthalic aldehyde (3) and its tetramethyl acetal (13), is elaborated. The carbonyl groups in dialdehydes 3 and 12 can be selectively involved in the reaction sequences leading to the introduction of both aliphatic and functional substituents in positions 1 and 4 of the benzene ring.

  DOI：

  10.1007/bf00698948
• 作为产物：
  描述：

  对溴苯甲醛 、 甲基丙烯酸甲酯 在 [Pd{C₆H₂-(CH₂CH₂NH₂)-(OMe)2-3,4}Br(PPh₃)] 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.33h， 以97%的产率得到(E)-methyl 3-(4-formylphenyl)-2-methylacrylate
  参考文献：
  名称：

  含磷-氮混合供体的单体原钯配合物在Heck反应中的应用

  摘要：

  合成了高藜芦胺和三苯基膦的[Pd {C 6 H 2（CH 2 CH 2 NH 2）-（OMe）2，3,4 } Br（PPh 3）]原钯原酸酯复合物，并研究了其在Heck偶联反应中的应用。对于芳基碘，溴化物甚至氯化物以及芳烃磺酰氯的Heck反应，已证明该络合物比相应的二聚催化剂更具活性。使用催化量的[Pd {C 6 H 2（CH 2 CH 2 NH 2）-（OMe）2，3,4} Br（PPh 3）]在130°C下于NMP中为热稳定且对氧不敏感的络合物。

  DOI：

  10.1016/j.tetlet.2011.07.036

文献信息

• Palladium-Catalyzed Heck Reaction of Aryl Chlorides under Mild Conditions Promoted by Organic Ionic Bases
  作者：Hua-Jian Xu、Yong-Qiang Zhao、Xin-Feng Zhou

  DOI：10.1021/jo201196a

  日期：2011.10.7

  An efficient Pd-catalyzed Heck reaction of aryl chlorides with olefins under mild conditions is described. High yields of products were achieved with n-Bu(4)N(+)OAc(-) as base. Significantly, the temperature of the Heck reaction of diverse nonactivated aryl chlorides can be lowered to 80 degrees C. The new reaction system can also tolerate a wider range of olefins.
• Biopolymer-metal complex wool–Pd as a highly active heterogeneous catalyst for Heck reaction in aqueous media
  作者：Shang Wu、Hengchang Ma、Xiaojie Jia、Yunmei Zhong、Ziqiang Lei

  DOI：10.1016/j.tet.2010.10.062

  日期：2011.1

  Heterogeneous palladium catalysts, a biopolymer complex wool-Pd, have been applied in water-mediated coupling reactions of aryl bromides without assistance of any phosphine ligands. The catalyst was characterized by XPS, ICP. The results showed that aryl bromides could carry out the coupling reaction with a variety of alkenes at 80 degrees C, in aqueous media under atmospheric condition. More importantly, the cheap catalyst is stable, which shows negligible metal leaching, and retain good activity for at least ten successive runs without any additional activation treatment. This approach would be very useful from a practical viewpoint. (C) 2010 Elsevier Ltd. All rights reserved.
• Applications of a monomeric orthopalladate complex containing mixed phosphorus–nitrogen donors in the Heck reaction
  作者：Abdol Reza Hajipour、Fatemeh Rafiee、Arnold E. Rouho

  DOI：10.1016/j.tetlet.2011.07.036

  日期：2011.9

  The [PdC6H2(CH2CH2NH2)-(OMe)2,3,4}Br(PPh3)] monomeric orthopalladate complex of homoveratrylamine and triphenylphosphine was synthesized and its application in Heck coupling reactions was investigated. This complex had been demonstrated to be more active than the corresponding dimeric catalyst for Heck reactions of aryl iodides, bromides and even chlorides and also arenesulfonyl chlorides. The cross-coupled

  合成了高藜芦胺和三苯基膦的[Pd C 6 H 2（CH 2 CH 2 NH 2）-（OMe）2，3,4 } Br（PPh 3）]原钯原酸酯复合物，并研究了其在Heck偶联反应中的应用。对于芳基碘，溴化物甚至氯化物以及芳烃磺酰氯的Heck反应，已证明该络合物比相应的二聚催化剂更具活性。使用催化量的[Pd C 6 H 2（CH 2 CH 2 NH 2）-（OMe）2，3,4} Br（PPh 3）]在130°C下于NMP中为热稳定且对氧不敏感的络合物。
• A novel approach to the synthesis of benzoic and cinnamic acid derivatives with nor-isoprenoid substituents
  作者：G. V. Kryshtal'、G. M. Zhdankina、E. P. Serebryakov

  DOI：10.1007/bf00698948

  日期：1993.5

  A novel strategy for the synthesis of 4-(nor-polyprenyl)-substituted benzoic acids and their esters of the general formula 1 as well as their vinylogs of the type 2, based on the use of terephthalic aldehyde (3) and its tetramethyl acetal (13), is elaborated. The carbonyl groups in dialdehydes 3 and 12 can be selectively involved in the reaction sequences leading to the introduction of both aliphatic and functional substituents in positions 1 and 4 of the benzene ring.