2-methyl-3-(3,4-dimethoxyphenyl)acrylic acid | 7350-60-9

• 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: 2-methyl-3-(3,4-dimethoxyphenyl)acrylic acid
• 英文别名: 3-(3,4-dimethoxyphenyl)-2-methylacrylic acid；3-(3,4-dimethoxy-phenyl)-2-methyl-acrylic acid；3-(3,4-Dimethoxy-phenyl)-2-methyl-acrylsaeure；3.4-Dimethoxy-α-methyl-zimtsaeure；Dimethylaetherhomokaffeesaeure；3-<3,4-Dimethoxy-phenyl>-2-methyl-acrylsaeure；3-(3,4-Dimethoxyphenyl)-2-methylprop-2-enoic acid
• CAS: 7350-60-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: HWFGFNBLIMJWLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(3,4-dimethoxyphenyl)acrylic acid 在 氯化亚砜 、 四溴化碳 、 nickel/aluminium alloy 、 四氯化锡 、 三苯基膦 、 sodium hydroxide 、 diborane(6) 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.5h， 生成 Methyl 2-[4,5-dimethoxy-2-(2-methyl-3-nitropropyl)benzoyl]benzoate
  参考文献：
  名称：

  Probing the Steric Space at the Floor of the D₁ Dopamine Receptor Orthosteric Binding Domain: 7α-, 7β-, 8α-, and 8β-Methyl Substituted Dihydrexidine Analogues

  摘要：

  To probe the space at the floor of the orthosteric ligand binding site in the dopamine D-1 receptor, four methylated analogues of dihydrexidine (DHX) were synthesized with substitutions at the 7 and 8 positions. The 8 alpha-axial, 8 beta-equatorial, and 7 alpha-equatorial were synthesized by photochemical cyclization of appropriately substituted N-benzoyl enamines, and the 7 beta-axial analogue was prepared by an intramolecular Henry reaction. All of the methylated analogues displayed losses in affinity when compared to DHX (20 nM): 8 beta-Me-ax-DHX (270 nM), 8 alpha-Me-eq-DHX (920 nM), 7 beta-Me-eq-DHX (6540 nM), and 7 alpha-Me-ax-DFLX (>10000 nM). Molecular modeling studies suggest that although the disruption of an aromatic interaction between Phe203(54.7) and Phe288(6.51) is the cause for the 14-fold loss in affinity associated with 8 beta-axial substitution, unfavorable steric interactions with Ser107(3.36) result in the more dramatic decreases in binding affinity suffered by the rest of the analogues.

  DOI：

  10.1021/jm200334c
• 作为产物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)-2-methylacrylic acid methyl ester 在 氢氧化钾 作用下， 生成 2-methyl-3-(3,4-dimethoxyphenyl)acrylic acid
  参考文献：
  名称：

  Tiemann; Kraaz, Chemische Berichte, 1882, vol. 15, p. 2063

  摘要：

  DOI：

文献信息

• 一种芳基丙酮类化合物的制备方法
  申请人：中国医科大学

  公开号：CN106045827B

  公开（公告）日：2018-04-20

  本发明属于有机合成领域，尤其涉及一种芳基丙酮类化合物的制备方法，具体技术方案如下：（1）以2‑甲基‑3‑芳基丙烯酸为起始原料，在有机溶剂中与氯化亚砜通过催化剂催化反应得到2‑甲基3‑芳基丙烯酰氯；减压蒸除有机溶剂后加入甲醇反应得到2‑甲基‑3‑芳基丙烯酸甲酯；（2）向步骤1所述的反应液中加入80％水合肼，反应得到2‑甲基‑3‑芳基丙烯酰基肼；（3）步骤2中的反应液减压蒸除甲醇，加入有机溶剂和稀盐酸后搅拌，另取亚硝酸钠配制成水溶液后滴加到搅拌的体系中，制得芳基丙酮；该方法生产成本低，反应条件温和，操作简单，收率高，适合工业化生产。
• 3-Methyl-3,4-dihydroisoquinolines and 3-Methyl-1,2,3,4-tetrahydroisoquinolines¹
  作者：Walter S. Ide、Johannes S. Buck

  DOI：10.1021/ja01859a050

  日期：1940.2
• Mueller; Richl, Chemische Berichte, 1943, vol. 76, p. 1119,1123
  作者：Mueller、Richl

  DOI：——

  日期：——
• FR2267764
  申请人：——

  公开号：——

  公开（公告）日：——
• Probing the Steric Space at the Floor of the D₁ Dopamine Receptor Orthosteric Binding Domain: 7α-, 7β-, 8α-, and 8β-Methyl Substituted Dihydrexidine Analogues
  作者：Juan Pablo Cueva、Alejandra Gallardo-Godoy、Jose I. Juncosa、Pierre A. Vidi、Markus A. Lill、Val J. Watts、David E. Nichols

  DOI：10.1021/jm200334c

  日期：2011.8.11

  To probe the space at the floor of the orthosteric ligand binding site in the dopamine D-1 receptor, four methylated analogues of dihydrexidine (DHX) were synthesized with substitutions at the 7 and 8 positions. The 8 alpha-axial, 8 beta-equatorial, and 7 alpha-equatorial were synthesized by photochemical cyclization of appropriately substituted N-benzoyl enamines, and the 7 beta-axial analogue was prepared by an intramolecular Henry reaction. All of the methylated analogues displayed losses in affinity when compared to DHX (20 nM): 8 beta-Me-ax-DHX (270 nM), 8 alpha-Me-eq-DHX (920 nM), 7 beta-Me-eq-DHX (6540 nM), and 7 alpha-Me-ax-DFLX (>10000 nM). Molecular modeling studies suggest that although the disruption of an aromatic interaction between Phe203(54.7) and Phe288(6.51) is the cause for the 14-fold loss in affinity associated with 8 beta-axial substitution, unfavorable steric interactions with Ser107(3.36) result in the more dramatic decreases in binding affinity suffered by the rest of the analogues.