4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid | 127404-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid
• 英文别名: (E)-4-(3,4,5-trimethoxyphenyl)but-3-enoic acid
• CAS: 127404-78-8
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: OKDKPMAYWSMTAN-SNAWJCMRSA-N

物化性质

• 沸点：
  425.6±40.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid 在 dirhodium tetraacetate 、 ABSA 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 1.5h， 生成 (E)-2-Hydroxy-4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid methyl ester
  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
• 作为产物：
  描述：

  巴豆酸 、 1-溴-3,4,5-三甲氧基苯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 生成 4-(3,4,5-trimethoxy-phenyl)-but-3-enoic acid
  参考文献：
  名称：

  Reaction of 2-butenoic acid dianion and its N-(4-methoxyphenyl)amide with methoxy-substituted arynes

  摘要：

  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.

  DOI：

  10.1021/jo00028a049

文献信息

• Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties
  作者：Arun K. Ghosh、Daniel S. Lee

  DOI：10.1021/acs.joc.9b00414

  日期：2019.5.17

  We describe here the enantioselective synthesis of (+)-monocerin and its acetate derivative. The present synthesis features an efficient optically active synthesis of the β-hydroxy-γ-lactone derivative with high enantiomeric purity using Sharpless dihydroxylation as the key step. The synthesis also highlights a tandem Lewis acid-catalyzed, oxocarbenium ion-mediated diastereoselective syn-allylation

  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。
• Butenoic or propenoic acid derivatives
  申请人：Eisai Co., Ltd.

  公开号：EP0344577A2

  公开（公告）日：1989-12-06

  A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.

  丁烯酸或丙烯酸衍生物具有下式，其中 G 为芳基或杂环，R11 和 R12 为氢基或烷基，X 为硫或氧，R2 和 R3 为氢，取代基如烷基，J 为吡啶基或苯基，R2、R3 和 J 之间可形成杂环，该衍生物在药理学领域非常有用。
• Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists
  作者：Remo Kranich、Anke S. Busemann、Daniel Bock、Sabine Schroeter-Maas、Diana Beyer、Bo Heinemann、Michael Meyer、Katrin Schierhorn、Rainer Zahlten、Gerhard Wolff、Ewald M. Aydt

  DOI：10.1021/jm060536g

  日期：2007.3.1

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.
• US5177089A
  申请人：——

  公开号：US5177089A

  公开（公告）日：1993-01-05
• A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds
  作者：Priyadarshanie Bulugahapitiya、Yannick Landais、Liliana Parra-Rapado、Denis Planchenault、Valéry Weber

  DOI：10.1021/jo961952j

  日期：1997.3.1

  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.