(E)-3-(2,3,4-trimethoxy-phenyl)-acrylic acid methyl ester | 116406-21-4

• 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)-3-(2,3,4-trimethoxy-phenyl)-acrylic acid methyl ester
• 英文别名: methyl 2,3,4-trimethoxycinnamate；2,3,4-trimethoxy-trans-cinnamic acid methyl ester；2,3,4-Trimethoxy-trans-zimtsaeure-methylester；methyl (2E)-3-(2,3,4-trimethoxyphenyl)acrylate；methyl (E)-3-(2,3,4-trimethoxyphenyl)prop-2-enoate
• CAS: 116406-21-4
• 化学式: C₁₃H₁₆O₅
• mdl: MFCD12034620
• 分子量: 252.267
• InChiKey: BDPRQDJNPJRLOB-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,3,4-trimethoxy-phenyl)-acrylic acid methyl ester 在 palladium on activated charcoal 硫酸 、 氢气 、 碘 、 magnesium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 19.83h， 生成 4,5,6-trimethoxy-1,1-dimethylindan
  参考文献：
  名称：

  Synthesis of the Core Structure of Acutumine

  摘要：

  The tricyclic core of the bioactive natural product acutumine has been synthesized. Key steps include an oxidative phenolic coupling to form a masked o-benzoquinone, an anionic oxy-Cope rearrangement to construct an all-carbon quaternary center, and a Michael-type cyclization to form an amine-bearing quaternary carbon. The target compound exists in solution as an enol, in contrast to related compounds that are ketones. A model explaining these observations is presented.

  DOI：

  10.1021/ol050020b
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 哌啶 、 硫酸 作用下， 生成 (E)-3-(2,3,4-trimethoxy-phenyl)-acrylic acid methyl ester
  参考文献：
  名称：

  Spaeth; Pailer; Gergely, Chemische Berichte, 1940, vol. 73, p. 795,802

  摘要：

  DOI：

文献信息

• Solid-Supported Green Synthesis of Substituted Hydrocinnamic Esters by Focused Microwave Irradiation
  作者：Vinod Kumar、Anuj Sharma、Arun K. Sinha

  DOI：10.1002/hlca.200690049

  日期：2006.3

  An efficient chemoselective hydrogenation protocol for substituted cinnamic esters is developed for the synthesis in quantitative yield of corresponding bioactive dihydrocinnamic esters with solid-supported palladium chloride/ammonium formate (cat.) in HCOOH/H2O 1 : 2 as a hydrogenating agent under focused-microwave irradiation for 10 min.

  开发了一种有效的取代肉桂酸酯的化学选择性氢化方案，用于以定量产率合成相应的生物活性二氢肉桂酸酯，其中在固相负载下，在HCOOH / H 2 O 1：2中加氢氯化钯/甲酸铵（cat。）作为氢化剂。 -微波照射10分钟。
• A practical synthesis of 3-indolyl α,β-unsaturated carbonyl compounds
  作者：Weiqi Wang、Tetsuya Ikemoto

  DOI：10.1016/j.tetlet.2005.03.195

  日期：2005.5

  β-unsaturated carbonyl compounds using methyl 3-methoxyacrylate, methyl 3,3-dimethoxypropionate, or 1,1-dimethoxy-3-butanone is reported. 35% HCl aqueous solution catalyzes this reaction efficiently in acetic acid. One of the most favorable substrates is 3-(4-fluorophenyl)-1-isopropyl-1H-indole, which reacts nearly quantitatively to give the corresponding α,β-unsaturated ester, and the scope of the reaction

  据报道，使用3-甲氧基丙烯酸甲酯，3,3-二甲氧基丙酸甲酯或1,1-二甲氧基-3-丁酮进行酸催化的3-吲哚基α，β-不饱和羰基化合物的合成。35％HCl水溶液在乙酸中有效催化该反应。最有利的底物之一是3-（4-氟苯基）-1-异丙基-1 H-吲哚，它几乎定量地反应生成相应的α，β-不饱和酯，并且反应范围可以扩大到一定程度。富电子苯衍生物。
• Process for Producing an Aromatic Unsaturated Compound
  申请人：Wang Weiqi

  公开号：US20080221337A1

  公开（公告）日：2008-09-11

  The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group, which comprises reacting (a) a compound of the formula (1) Ar—H  (1) wherein Ar has the same meaning as defined above with (b) a compound of the formula (2) wherein Y has the same meaning as defined above, and Z represents a lower alkoxy, or a compound of the formula (3) wherein Y and Z have the same meanings as defined above, in the presence of (c) an acid or a compound which generates a mineral acid by its hydrolysis.

  本发明提供了一种制备公式（4）的芳香不饱和化合物的方法，其中Ar代表可选择取代的芳香基团或可选择取代的杂环芳香基团，Y代表电子提取基团，包括以下步骤：(a)将公式（1）的化合物Ar-H（1）与(b)公式（2）的化合物反应，其中Y具有与上述定义相同的含义，Z代表低级烷氧基，或公式（3）的化合物，其中Y和Z具有与上述定义相同的含义，在(c)酸或通过其水解生成矿酸的化合物的存在下。
• PROCESS FOR PRODUCING AN AROMATIC UNSATURATED COMPOUND
  申请人：WANG Weiqi

  公开号：US20090111999A1

  公开（公告）日：2009-04-30

  The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group, which comprises reacting (a) a compound of the formula (1) Ar—H  (1) wherein Ar has the same meaning as defined above with (b) a compound of the formula (2) wherein Y has the same meaning as defined above, and Z represents a lower alkoxy, or a compound of the formula (3) wherein Y and Z have the same meanings as defined above, in the presence of (c) an acid or a compound which generates a mineral acid by its hydrolysis.

  本发明提供了一种生产芳香不饱和化合物的方法，该化合物的化学式为（4），其中Ar表示可选取代的芳香基团或可选取代的杂芳基团，Y表示电子提取基团，该方法包括在(d)酸或生成矿酸的化合物的存在下，将(a)化合物（1）Ar—H（1）（其中Ar的含义如上所定义）与(b)化合物（2）反应，该化合物的化学式为Y与上述定义相同，Z表示较低的烷氧基，或者与(c)化合物（3）反应，该化合物的化学式中Y和Z的含义与上述定义相同。
• Process for producing an aromatic unsaturated compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：US07939674B2

  公开（公告）日：2011-05-10

  The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group, which comprises reacting (a) a compound of the formula (1) Ar—H  (1) wherein Ar has the same meaning as defined above with (b) a compound of the formula (2) wherein Y has the same meaning as defined above, and Z represents a lower alkoxy, or a compound of the formula (3) wherein Y and Z have the same meanings as defined above, in the presence of (c) an acid or a compound which generates a mineral acid by its hydrolysis.

  本发明提供了一种制备芳香不饱和化合物的方法，其中该化合物的化学式为(4)，其中Ar表示可选取代的芳基或可选取代的杂芳基，Y表示电子吸引基团，该方法包括在(d) 酸或通过水解产生矿酸的化合物的存在下，反应(a) 化合物的化学式为(1) Ar-H (1)，其中Ar具有上述定义的相同含义，与(b) 化合物的化学式为(2) 其中Y具有上述定义的相同含义，Z表示较低的烷氧基，或者化合物的化学式为(3) 其中Y和Z具有上述定义的相同含义。