methyl 4-(3,4,5-trimethoxyphenyl)-3-butenoate | 137744-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-(3,4,5-trimethoxyphenyl)-3-butenoate
• 英文别名: methyl (E)-4-(3,4,5-trimethoxyphenyl)but-3-enoate
• CAS: 137744-79-7
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: HAVWWQAOVIUTKT-AATRIKPKSA-N

物化性质

• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(3,4,5-trimethoxyphenyl)-3-butenoate 在 甲基磺酰胺 、 AD-mix-β 、 四丁基碘化铵 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 95.0h， 生成
  参考文献：
  名称：

  (+)-Monocerin（一种具有有效抗疟特性的二氢异香豆素衍生物）的对映选择性全合成。

  摘要：

  我们在这里描述了 (+)-monocerin 及其乙酸酯衍生物的对映选择性合成。本合成的特点是使用 Sharpless 二羟基化作为关键步骤，高效光学活性合成具有高对映体纯度的 β-羟基-γ-内酯衍生物。该合成还强调了串联路易斯酸催化、氧碳鎓离子介导的非对映选择性顺烯丙基化反应，以及甲氧基甲基促进的亚甲基化反应。我们用各种路易斯酸研究了该反应。CrO3 介导的选择性氧化异色满提供了相应的内酯衍生物。该合成非常有效，可用于衍生物的制备。

  DOI：

  10.1021/acs.joc.9b00414
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙醛 在 三乙胺 作用下， 反应 1.0h， 生成 methyl 4-(3,4,5-trimethoxyphenyl)-3-butenoate
  参考文献：
  名称：

  A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds

  摘要：

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.

  DOI：

  10.1021/jo961952j

文献信息

• Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes
  作者：Abdul Rakeeb Deshmukh、Tran Long、Edward R. Biehl

  DOI：10.1021/jo00028a049

  日期：1992.1

  N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide 9 (85-90%) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15%). Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amounts of 4-aryl-2-butenoic acids 15'. The exclusive low temperature (-30 to -40-degrees-C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures. The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.