methyl (E)-2,3-bis(3,4-dimethoxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl (E)-2,3-bis(3,4-dimethoxyphenyl)acrylate
• 英文别名: methyl (E)-2,3-bis(3,4-dimethoxyphenyl)propenoate；methyl (E)-2,3-bis(3,4-dimethoxyphenyl)prop-2-enoate
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: MHYOPIANRZHZKR-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-2,3-bis(3,4-dimethoxyphenyl)acrylate 在 lithium aluminium tetrahydride 作用下， 以69%的产率得到(E)-2,3-bis(3,4-dimethoxyphenyl)-2-propen-1-ol
  参考文献：
  名称：

  Acid Reactions of the Lignin Model 1,2-Bis(3,4-dimethoxyphenyl)-1,3-propanediol.

  摘要：

  1,2-Bis(3,4-dimethoxyphenyl)-1,3-propanediol on acid treatment [refluxing with 0.1 M (or 0.2 M) acid in dioxane-water (9:1)1 undergoes two competing reactions: a reverse Prins reaction leading to (E)-3,3',4,4'-tetramethoxystilbene (and formaldehyde) and a dehydration with formation of aryl-substituted allyl alcohols [the E and Z forms of 2,3-bis(3,4-dimethoxyphenyl)-2-propen-1-ol, 1,2-bis (3,4-dimethoxyphenyl)-2-propen-1-ol] that are comparatively slowly converted into a series of carbonyl compounds [1,2-bis (3,4-dimethoxyphenyl)-1-propanone, 2,2-bis(3,4-dimethoxyphenyl)propanal, 1,1-bis (3,4-dimethoxyphenyl )-2-propanone, 2,3-bis(3,4-dimethoxyphenyl) propanal] and 2-(3,4-dimethoxyphenyl )-5,6-dimethoxy-1H-indene. HBr (and to a lesser extent HCl) catalyses the formation of allyl alcohols while only traces of these compounds are formed when CH3SO3H is used as the catalyst [(E)-3,3',4,4' tetramethoxystilbene is the predominant reaction product]. HBr promotes the formation of 1,2-bis(3,4-dimethoxyphenyl)-1-propanone from the intermediate (E)-2,3-bis(3,4-dimethoxyphenyl)-2-propen-1-ol. alpha-Chloromethyl-3,3',4,4'-tetramethoxystilbene and alpha-bromomethyl-3,3',4,4'-tetramethoxystilbene are formed in the reactions catalysed by HCl and HBr, respectively. The preparation and/or isolation of most of the detected acidolysis products is described and their stereochemistry is elucidated. A stereoselective synthesis of threo-1,2-bis (3,4-dimethoxyphenyl)-1,3-propanediol involving hydroboration-oxidation of (E)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid is reported.

  DOI：

  10.3891/acta.chem.scand.51-0431
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 在 硫酸 、 乙酸酐 作用下， 以 三乙胺 为溶剂， 反应 24.0h， 生成 methyl (E)-2,3-bis(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  二叔丁基过氧化物促进的2,3-二取代苯基丙烯酸及其衍生物的氧化分子内偶联

  摘要：

  聚甲氧基取代的菲-9羧酸或其甲酯是合成tylophora生物碱及其类似物的关键中间体。未官能化的2，3-二取代的苯基丙烯酸和过氧化二叔丁基促进的衍生物的分子内氧化偶联反应以高收率得到上述中间体。该方法温和的反应条件和简便的纯化步骤为合成菲提供了一种新方法。

  DOI：

  10.1016/j.cclet.2013.11.004

文献信息

• Intramolecular Dehydrogenative Coupling of 2,3-Diaryl Acrylic Compounds: Access to Substituted Phenanthrenes
  作者：Vijay Gupta、V. U. Bhaskara Rao、Tamal Das、Kumar Vanka、Ravi P. Singh

  DOI：10.1021/acs.joc.6b00507

  日期：2016.7.1

  environmentally benign intramolecular dehydrogenative coupling of various 1,2-diarylethylenes for the synthesis of phenanthrenes in excellent yield has been described. This new methodology uses ceric ammonium nitrate (CAN) as a promoter at room temperature and has been extended to intermolecular synthesis of biaryl compounds. The electron transfer from methoxyarene to cerium leads to cationic radical formation

  已经描述了用于以优异的产率合成菲的各种1,2-二芳基乙烯的简单，容易且对环境无害的分子内脱氢偶联。这种新的方法在室温下使用硝酸铈铵（CAN）作为促进剂，并已扩展到联芳基化合物的分子间合成。电子从甲氧基芳烃转移到铈导致阳离子自由基的形成，其进一步进行分子内偶联。通过EPR光谱进行的初步机理研究和密度泛函理论计算得出了相似的观点。
• A Novel Sodium Nitrite-Catalyzed Oxidative Coupling for Constructing Polymethoxyphenanthrene Rings
  作者：Bo Su、Ling Li、Yanna Hu、Yuxiu Liu、Qingmin Wang

  DOI：10.1002/adsc.201100578

  日期：2012.2

  An efficient and green oxidative coupling for the direct construction of polymethoxyphenanthrene rings has been developed, which uses environment-friendly sodium nitrite as catalyst and oxygen as terminal oxidant. This methodology also provides an alternative possibility for forming biaryl products.

  已经开发出用于直接构建聚甲氧基菲环的高效且绿色的氧化偶联剂，该偶联剂使用环境友好的亚硝酸钠作为催化剂，氧气作为末端氧化剂。该方法学还提供了形成联芳基产物的另一种可能性。
• Design, synthesis and biological evaluation of 1-phenanthryl-tetrahydroisoquinoline derivatives as novel p21-activated kinase 4 (PAK4) inhibitors
  作者：Shuai Song、Xiaodong Li、Jing Guo、Chenzhou Hao、Yan Feng、Bingyu Guo、Tongchao Liu、Qiaoling Zhang、Zhen Zhang、Ruijuan Li、Jian Wang、Bin Lin、Feng Li、Dongmei Zhao、Maosheng Cheng

  DOI：10.1039/c5ob00037h

  日期：——

  Following the screening of an in-house natural product database, 1-phenanthryltetrahydroisoquinoline analogues were synthesized as novel PAK4 inhibitors.

  通过对内部天然产物数据库的筛选，合成了作为新型PAK4抑制剂的1-苯并基四氢异喹啉类似物。
• Oxidative intramolecular coupling of 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide
  作者：De-Rong Ji、Hua Yang、Xiao-Jing Zhao、Hao Yang、Yang-Zhao Liu、Dai-Hui Liao、Chun Feng、Cheng-Gang Zhang

  DOI：10.1016/j.cclet.2013.11.004

  日期：2014.2

  Polymethoxy-substituted phenanthrene-9-carboxylic acids or their methylate are key intermediates for the synthesis of tylophora alkaloids and their analogs. An intramolecular oxidative coupling reaction of unfunctionalized 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide gave above intermediates in high yields. The mild reaction conditions and easy purification

  聚甲氧基取代的菲-9羧酸或其甲酯是合成tylophora生物碱及其类似物的关键中间体。未官能化的2，3-二取代的苯基丙烯酸和过氧化二叔丁基促进的衍生物的分子内氧化偶联反应以高收率得到上述中间体。该方法温和的反应条件和简便的纯化步骤为合成菲提供了一种新方法。
• A Simple and Efficient Oxidative Coupling of Aromatic Nuclei Mediated by Manganese Dioxide
  作者：Qingmin Wang、Kailiang Wang、Yanna Hu、Zheng Li、Meng Wu、Zhihui Liu、Bo Su、Ao Yu、Yu Liu

  DOI：10.1055/s-0029-1219237

  日期：2010.4

  Oxidative intramolecular coupling of the aryl rings of various stilbenes for direct construction of the phenanthrene ring system is promoted efficiently by manganese dioxide-trifluoroacetic acid at room temperature in excellent yields. This approach is also applied to the intermolecular biaryl coupling of 2-naphthols, 2-naphthalenethiol, 2-naphthylamine, a phenol ether and a phenol under very mild

  通过二氧化锰-三氟乙酸在室温下以优异的产率有效地促进了用于直接构建菲环系统的各种斯蒂芬烯的芳基环的氧化性分子内偶联。该方法也适用于在非常温和的条件下将2-萘酚，2-萘硫醇，2-萘胺，苯酚醚和苯酚进行分子间联芳基偶联。提出了一种电子转移机理，其中二氧化锰用作二电子氧化剂。 氧化偶合-芳核-二氧化锰-菲-分子间联芳基偶合