methyl 3,4-dimethoxy-α-(3,4-dimethoxyphenyl)cinnamate | 172922-64-4

• 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 3,4-dimethoxy-α-(3,4-dimethoxyphenyl)cinnamate
• 英文别名: (Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid methyl ester；methyl (Z)-2,3-bis(3,4-dimethoxyphenyl)propenoate；methyl (Z)-2,3-bis(3,4-dimethoxyphenyl)acrylate；3,4-Dimethoxy-α-(3,4-dimethoxyphenyl)-zimtsaeuremethylester；methyl (Z)-2,3-bis(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 172922-64-4
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: MHYOPIANRZHZKR-GDNBJRDFSA-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 3,4-dimethoxy-α-(3,4-dimethoxyphenyl)cinnamate 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以55%的产率得到(Z)-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 乙酸酐 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 methyl 3,4-dimethoxy-α-(3,4-dimethoxyphenyl)cinnamate
  参考文献：
  名称：

  Cragg, John E.; Herbert, Richard B.; Jackson, Frederick B., Journal of the Chemical Society. Perkin transactions I, 1982, # 10, p. 2477 - 2486

  摘要：

  DOI：

文献信息

• 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
• Iron(III) Chloride Catalyzed Oxidative Coupling of Aromatic Nuclei
  作者：Kailiang Wang、Maoyun Lü、Ao Yu、Xiaoqing Zhu、Qingmin Wang

  DOI：10.1021/jo8021633

  日期：2009.1.16

  Easily available and nontoxic FeCl3 catalyzes intramolecular oxidative coupling for the direct construction of the phenanthrene ring using meta-chloroperbenzoic acid as sole oxidant at room temperature in excellent yields. The mechanistic investigations show that FeCl3-catalyzed coupling proceeds through the heterolytic coupling (A+ + B). The catalytic approach has been applied to intermolecular biaryl

  易获得且无毒的FeCl 3催化分子内氧化偶联，可在室温下使用间氯过苯甲酸作为唯一氧化剂以高收率直接构建菲环。机理研究表明，FeCl 3催化的偶联通过杂化偶联（A + + B）进行。该催化方法已应用于2-萘酚和酚醚的分子间联芳基偶联。
• Synthesis of Phenanthro[9,10-<i>b</i>]indolizidin-9-ones, Phenanthro[9,10-<i>b</i>]quinolizidin-9-one, and Related Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation
  作者：Satoshi Yamashita、Nobuhito Kurono、Hisanori Senboku、Masao Tokuda、Kazuhiko Orito

  DOI：10.1002/ejoc.200801047

  日期：2009.3

  10-b]indolizidin-9-ones, phenanthro[9,10-b]quinolizidin-9-one, and related benzolactams were synthesized by benzolactam ring formation using Pd(OAc)2-catalyzed direct aromatic carbonylation. This also constitutes a formal synthesis of the representative phenanthroindolizidine and -quinolizidine alkaloids (±)-tylophorine, (±)-antofine, and (±)-cryptopleurine.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  菲 [9,10-b] indolizidin-9-ones、菲 [9,10-b] quinolizidin-9-one 和相关苯并内酰胺是通过使用 Pd(OAc)2 催化的直接芳香羰基化通过苯内酰胺环形成合成的。这也构成了代表性的菲吲哚里西啶和-喹唑西啶生物碱 (±)-tylophorine、(±)-antofine 和 (±)-cryptopleurine 的正式合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Iron(III) Chloride Catalyzed Oxidative Coupling Reaction of 1,2-Diarylethylene Derivatives
  作者：Derong Ji、Lidan Su、Keqing Zhao、Biqin Wang、Ping Hu、Chun Feng、Shikai Xiang、Hua Yang、Chenggang Zhang

  DOI：10.1002/cjoc.201300308

  日期：2013.8

  A nontoxic FeCl3 catalyzed intramolecular oxidative coupling reaction was developed for mild synthesis of a series of phenanthrenes with different substituents. The method involves cross dehydrogenative coupling of a variety of 1,2‐diarylethylene derivatives with di‐tert‐butylperoxide (DTBP) as a sole oxidant at room temperature in CH2Cl2/TFA (9:1 V/V) to yield phenanthrenes in good to excellent yields

  开发了一种无毒的FeCl 3催化的分子内氧化偶联反应，用于轻度合成一系列具有不同取代基的菲。该方法涉及在室温下在CH 2 Cl 2 / TFA（9：1 V / V）中将多种1,2-二芳基乙烯衍生物与二叔丁基过氧化物（DTBP）作为唯一氧化剂进行交叉脱氢偶联以生成菲产量高到极好。