dimethyl 2,6-dimethyl-4-(3-thiophenyl)-1,4-dihydropyridine-3,5-dicarboxylate | 112369-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 2,6-dimethyl-4-(3-thiophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: dimethyl 2,6-dimethyl-4-(3-thienyl)-1,4-dihydropyridine-3,5-dicarboxylate；3,5-dicarbomethoxy-2,6-dimethyl-4-(3-thienyl)-1,4-dihydropyridine；dimethyl 2,6-dimethyl-4-(3-thienyl)-1.4-dihydro-3,5-pyridinedicarboxylate；Dimethyl 2,6-dimethyl-4-thiophen-3-yl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 112369-88-7
• 化学式: C₁₅H₁₇NO₄S
• 分子量: 307.37
• InChiKey: HARSPKJVDAIVPN-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C(Solv: methanol (67-56-1))
• 沸点：
  431.0±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,6-dimethyl-4-(3-thiophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 在 sodium hydroxide 、 硫酸 、 硝酸 、 一水合肼 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.0h， 生成 5,7-dimethyl-8-oxo-6-aza-8H-indeno<2,1-b>thiophene-4-carboxylic acid
  参考文献：
  名称：

  Heude, Florence; Sevricourt, Michel Cugon de; Rault, Sylvain, Heterocycles, 1987, vol. 26, # 6, p. 1535 - 1540

  摘要：

  DOI：
• 作为产物：
  描述：

  3-噻吩甲醛 、 乙酰乙酸甲酯 在 alumina 、 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 以93%的产率得到dimethyl 2,6-dimethyl-4-(3-thiophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  一种有效的和可回收的三维印刷的α-Al 2 ö 3催化剂对于该多组分生物活性组件的杂环

  摘要：

  报道了一种催化方法，该方法能够有效，操作简单且环保地合成各种1,4-二氢吡啶和3,4-二氢嘧啶-2（1 H）-one，包括一些相关药物和药理活性衍生物。该策略基于使用3D打印的Al 2 O 3木桩材料，该材料经过烧结以产生具有受控孔隙率和显着催化性能的刚性结构。3D打印的Al 2 O 3催化剂在Biginelli和Hantzsch反应中显示出路易斯酸的显着功效，并且可以回收并重复使用十次而不会降低活性。卓越的E 因素，出色的可回收性和可扩展性，广泛的底物范围，短的反应时间，优异的产率，无溶剂条件和易于分离的程序是该方法的关键特征。

  DOI：

  10.1016/j.apcata.2016.11.031

文献信息

• Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization
  作者：Anamika Khaskel、Pranjit Barman

  DOI：10.1002/hc.21308

  日期：2016.3

  An efficient, cost-effective and simple protocol has been developed for the synthesis of Hantzsch 1,4-dihydropyridines and their oxidation into pyridines using benzyltrimethylammonium fluoride hydrate as an excellent catalyst under solvent-free condition. All of the products synthesized by this method are characterized by various spectroscopic methods (IR, 1H NMR, 13C NMR, and DEPT).

  已开发出一种高效、经济且简单的方案，用于在无溶剂条件下使用苄基三甲基氟化铵水合物作为优异催化剂合成 Hantzsch 1,4-二氢吡啶并将其氧化成吡啶。通过该方法合成的所有产品均通过各种光谱方法（IR、1H NMR、13C NMR 和 DEPT）进行表征。
• Multicomponent diversity-oriented synthesis of symmetrical and unsymmetrical 1,4-dihydropyridines in recyclable glycine nitrate (GlyNO₃) ionic liquid: a mechanistic insight using Q-TOF, ESI-MS/MS
  作者：Rajesh Kumar、Nitin H. Andhare、Amit Shard、Richa Richa、Arun Kumar Sinha

  DOI：10.1039/c4ra02169j

  日期：——

  unsymmetrical 1,4 DHPs under identical reaction conditions are added benefits to its practical utility. Furthermore, progress of the reaction was monitored by Q-TOF, direct infusion electrospray ionization mass spectrometry (ESI-MS), and key cationic intermediates involved in the reaction have been further identified by a tandem MS experiment (Q-TOF, ESI-MS/MS), which served as the proof of concept

  多组分反应是产生具有化学多样性的，具有高原子经济性的一组多功能杂环基序的引人注目的策略，从而使转换绿色。如果考虑催化剂的可回收性，相容性和精确机理的探索，这些策略将变得更加丰富。为此，一种廉价且可循环利用的硝酸甘氨酸硝酸盐（GlyNO 3）离子液体已被有效地用于通过以下途径获得高达93％的收率的各种取代的对称和不对称的1,4-二氢吡啶三个组成部分和四个组成部分。在相同的反应条件下获得对称和不对称1,4 DHP的催化剂可回收性和相容性为其实用性带来了更多好处。此外，通过Q-TOF，直接注入电喷雾电离质谱（ESI-MS）监测反应进程，并通过串联MS实验（Q-TOF，ESI-MS）进一步确定了反应中涉及的关键阳离子中间体/ MS），作为机械模型概念的证明。这是第一份揭示汉茨反应主要遵循四个竞争反应途径中的二酮途径的报告。
• Cerebral Antihypoxic Activity of New Thienyldihydropyridines.
  作者：Michel BOULOUARD、Josette LOUCHAHI-RAOUL、Florence HEUDE、Marie-Anne QUERMONNE、Michel CUGNON DE SEVRICOURT、Sylvain RAULT、Max ROBBA

  DOI：10.1248/cpb.43.162

  日期：——

  New thienyldihydropyridines were synthesized according to Hantzsch's method. The antihypoxic activity of these compounds was compared with that of three reference phenyldihydropyridines by means of the skin conductance reaction (SCR)-hypoxia test.

  根据 Hantzsch 方法合成了新的噻吩基二氢吡啶。通过皮肤传导反应（SCR）-缺氧试验，比较了这些化合物与三种参考苯基二氢吡啶类化合物的抗缺氧活性。
• Compounds for inhibiting beta-amyloid production and methods of identifying the compounds
  申请人：Mullan J. Michael

  公开号：US20060188938A1

  公开（公告）日：2006-08-24

  Provided are compounds useful for treating diseases associated with a cerebral accumulation of Alzheimer's amyloid, such as Alzheimer's disease. Also provided are methods for screening for such compounds, by measuring capacitative calcium entry in cells which optionally overexpress APP or a fragment thereof. Also provided are methods of treating or reducing the risk of developing β-amyloid production, β-amyloid deposition, β-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of compounds which decrease β-amyloid production and capacitative calcium entry in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of compounds which inhibit capacitative calcium entry in cells.

  提供了对治疗与阿尔茨海默病相关的脑部淀粉样蛋白沉积疾病（如阿尔茨海默病）有用的化合物。还提供了筛选此类化合物的方法，通过测量细胞中的电容性钙离子入流，该细胞可选择过表达APP或其片段。还提供了通过给予治疗有效量的化合物来治疗或降低β-淀粉样蛋白产生、β-淀粉样蛋白沉积、β-淀粉样蛋白神经毒性（包括tau异常的超磷酸化）和与阿尔茨海默病相关的微胶质细胞病的风险的方法，这些化合物降低细胞中的β-淀粉样蛋白产生和电容性钙离子入流。此外，还提供了通过给予诊断有效量的化合物来诊断动物或人类中与阿尔茨海默病相关的脑部淀粉样蛋白沉积疾病的方法，这些化合物抑制细胞中的电容性钙离子入流。
• Compounds and Combinations Thereof for Inhibiting Beta-Amyloid Production and Methods of Use Thereof
  申请人：Paris Daniel

  公开号：US20080058330A1

  公开（公告）日：2008-03-06

  Provided are compounds which can be used in combination for treating diseases associated with a condition associated with cerebral accumulation of Alzheimer's amyloid, such as Alzheimer's disease. Also provided are methods of treating or reducing the risk of developing β-amyloid production, β-amyloid deposition, β-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of compounds which in combination can decrease β-amyloid production and capacitative calcium entry in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of the compounds.

  提供了一些化合物，可以组合使用来治疗与阿尔茨海默病淀粉样蛋白相关的疾病，如阿尔茨海默病。还提供了一种方法，通过给予治疗有效量的化合物组合来减少β-淀粉样蛋白的产生和细胞中的电容性钙离子进入，从而治疗或降低发生β-淀粉样蛋白产生、β-淀粉样蛋白沉积、β-淀粉样蛋白神经毒性（包括tau异常过度磷酸化）和与阿尔茨海默病淀粉样蛋白相关的微胶质病变。此外，还提供了一种方法，通过给予诊断有效量的化合物来诊断动物或人类中与阿尔茨海默病淀粉样蛋白相关的疾病。