(Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid | 172922-62-2

• 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: (Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid
• 英文别名: (2Z)-2,3-bis(3,4-dimethoxyphenyl)acrylic acid；(Z)-2,3-bis(3,4-dimethoxyphenyl)acrylic acid；3,4-dimethoxy-α-(3,4-dimethoxyphenyl)cinnamic acid；(Z)-2,3-bis(3,4-dimethoxyphenyl)prop-2-enoic acid
• CAS: 172922-62-2
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: LRQNEBDGXKAKHW-ZROIWOOFSA-N

物化性质

• 熔点：
  216-217 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  479.7±40.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid 在 manganese(IV) oxide 、 三氟乙酸 作用下， 反应 6.0h， 以95%的产率得到2,3,6,7-四甲氧基-9-羧基菲
  参考文献：
  名称：

  二氧化锰介导的芳香核的简单高效氧化偶联

  摘要：

  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

  DOI：

  10.1055/s-0029-1219237
• 作为产物：
  描述：

  2,3-bis(3,4-dimethoxyphenyl)-2-hydroxypropanoic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 1.0h， 以58%的产率得到(Z)-2,3-bis(3,4-dimethoxyphenyl)propenoic acid
  参考文献：
  名称：

  (Z)-2,3-Bis(3,4-dimethoxyphenyl)propenoic Acid

  摘要：

  The crystal structure determination demonstrates unambiguously that the title compound, C19H20O6, has the Z configuration. The compound was synthesized starting from 2,3-bis(3,4-dimethoxyphenyl)-2-hydroxypropanoic acid, which was in turn obtained by an alkaline treatment of trans-1,3-bis(3,4-dimethoxyphenyl)-2,3-epoxy-1-propanone. H-1 NMR data for the title compound and its methyl ester are reported.

  DOI：

  10.1107/s0108270195009140

文献信息

• 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。
• New route to o-terphenyls: application to the synthesis of 6,7,10,11-tetramethoxy-2-(methoxycarbonyl)triphenylene
  作者：Elisabetta Brenna、Claudio Fuganti、Stefano Serra

  DOI：10.1039/a707738f

  日期：——

  The hydroxy-o-terphenylcarboxylic acid esters 6a–f have been prepared by benzannulation of the 5,6-diaryl-3-methoxycarbonylhexa-3,5-dienoic acids 5a–f using triethylamine–ethyl chloroformate. The application of this new synthesis of triphenylenes is illustrated through the synthesis of 2-methoxycarbonyl-6,7,10,11-tetramethoxytriphenylene 9.

  羟基-o-三苯甲酸酯6a–f是通过使用三乙胺-氯仿酸乙酯对5,6-二芳基-3-甲氧基羧基六烯酸5a–f进行苯环化反应合成的。这种新型三苯烯合成方法的应用通过合成2-甲氧基羧基-6,7,10,11-四甲氧基三苯烯9得以展示。
• 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。
• 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)