2-methyl-3-p-tolylacrylic acid | 25860-59-7

• 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-p-tolylacrylic acid
• 英文别名: α-Methyl-p-methylzimtsaeure；α-Methyl-β-p-tolyl-acrylsaeure；α-p-Tolyl-α-propylen-β-carbonsaeure；2-Methyl-3-p-tolyl-acrylsaeure；4.α-Dimethyl-zimtsaeure；2-Propenoic acid, 2-methyl-3-(4-methylphenyl)-, (2E)-；2-methyl-3-(4-methylphenyl)prop-2-enoic acid
• CAS: 25860-59-7
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: OPOOYZXNEUXLBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C
• 沸点：
  306.5±11.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-p-tolylacrylic acid 在 硫酸 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~80.0 ℃ 、1.01 MPa 条件下， 反应 44.5h， 生成 ethyl 2-(2,5-dimethyl-1H-inden-3-yl)acetate
  参考文献：
  名称：

  Synthesis and SAR study of modulators inhibiting tRXRα-dependent AKT activation

  摘要：

  RXR alpha represents an intriguing and unique target for pharmacologic interventions. We recently showed that Sulindac and a designed analog could bind to RXR alpha and modulate its biological activity, including inhibition of the interaction of an N-terminally truncated RXR alpha (tRXR alpha) with the p85 alpha regulatory subunit of phosphatidylinositol-3-OH kinase (PI3K). Here we report the synthesis, testing and SAR of a series of novel analogs of Sulindac as potential modulators for inhibiting tRXR alpha-dependent AKT activation. A new compound 30 was identified to have improved biological activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.012
• 作为产物：
  描述：

  methyl (E)-2-methyl-3-(4-methylphenyl)acrylate 生成 2-methyl-3-p-tolylacrylic acid
  参考文献：
  名称：

  v. Auwers, Justus Liebigs Annalen der Chemie, 1917, vol. 413, p. 266

  摘要：

  DOI：

文献信息

• Iridium-Catalyzed Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids
  作者：Shen Li、Shou-Fei Zhu、Can-Ming Zhang、Song Song、Qi-Lin Zhou

  DOI：10.1021/ja802399v

  日期：2008.7.1

  A highly efficient iridium-catalyzed hydrogenation of alpha,beta-unsaturated carboxylic acids has been developed by using chiral spiro-phosphino-oxazoline ligands, affording alpha-substituted chiral carboxylic acids in exceptionally high enantioselectivities and reactivities.

  已经通过使用手性螺-膦基-恶唑啉配体开发了一种高效的铱催化氢化 α,β-不饱和羧酸，从而以极高的对映选择性和反应性提供 α-取代的手性羧酸。
• Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation
  作者：Long-Qing Zhu、Xiao-Hong Fan、Jun-Fang Li、Jin-Hong Chen、Yan Liang、Xiao-Ling Hu、Shu-Meng Ma、Xiang-Yong Hao、Tao Shi、Zhen Wang

  DOI：10.1016/j.bmcl.2021.128106

  日期：2021.7

  suggested that the mechanism of action may be that it interfered the formation of active dimeric iNOS but not affected transcription and translation. Furthermore, its good performance of anti-inflammatory effect on LPS-induced multiple inflammatory cytokines production, carrageenan-induced paw edema, and endotoxin-induced septic mice, was observed. We believe that these findings would provide an idea for the

  炎症作为宿主对刺激的过度免疫反应，参与了许多疾病的发展。为了发现新的抗炎剂，并基于我们之前对海洋天然产物菊酰胺 B 的合成工作，合成了它和一系列衍生物，并评估了它们对抑制 LPS 诱导的 NO 产生的抗炎活性。然后进行初步的构效关系。其中，Chrysamide B 是最有效的抗炎剂，具有低细胞毒性和强烈抑制 NO 产生（IC 50  = 0.010 μM）和 iNOS 活性（IC 50 = 0.082 μM) 在 LPS 刺激的 RAW 264.7 细胞中。初步研究表明，其作用机制可能是干扰了活性二聚体 iNOS 的形成，但不影响转录和翻译。此外，观察到其对 LPS 诱导的多种炎性细胞因子产生、角叉菜胶诱导的爪水肿和内毒素诱导的败血症小鼠具有良好的抗炎作用。我们相信这些发现将为未来这些类似物的进一步修饰和研究提供思路。
• Enantio- and diastereoselective boron conjugate addition to α-alkyl α,β-unsaturated esters
  作者：Meng Li、Guang-Rui Peng、Xuan Yang、Zhen-Ning Ma、Jian-Bo Xie

  DOI：10.1039/d2ob01928k

  日期：——

  We developed a copper-catalyzed enantio- and diastereoselective boron conjugate addition to α-alkyl α,β-unsaturated esters under base-free conditions. The approach showed excellent enantioselectivities (87–99% ee) and moderate to good conversions (51–99%), albeit with moderate diastereoselectivities (1 : 1–17 : 1 dr). The synthetic utility of this protocol was demonstrated.

  我们在无碱条件下开发了一种铜催化的对映选择性和非对映选择性硼共轭加成到 α-烷基 α,β-不饱和酯中。该方法显示出出色的对映选择性 (87–99% ee) 和中等至良好的转化率 (51–99%)，尽管具有中等的非对映选择性 (1 : 1–17 : 1 dr)。证明了该协议的综合效用。
• FR2267764
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and SAR study of modulators inhibiting tRXRα-dependent AKT activation
  作者：Zhi-Gang Wang、Liqun Chen、Jiebo Chen、Jian-Feng Zheng、Weiwei Gao、Zhiping Zeng、Hu Zhou、Xiao-kun Zhang、Pei-Qiang Huang、Ying Su

  DOI：10.1016/j.ejmech.2013.01.012

  日期：2013.4

  RXR alpha represents an intriguing and unique target for pharmacologic interventions. We recently showed that Sulindac and a designed analog could bind to RXR alpha and modulate its biological activity, including inhibition of the interaction of an N-terminally truncated RXR alpha (tRXR alpha) with the p85 alpha regulatory subunit of phosphatidylinositol-3-OH kinase (PI3K). Here we report the synthesis, testing and SAR of a series of novel analogs of Sulindac as potential modulators for inhibiting tRXR alpha-dependent AKT activation. A new compound 30 was identified to have improved biological activity. (C) 2013 Elsevier Masson SAS. All rights reserved.