ethyl 2(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetate | 1040075-47-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetate
• 英文别名: ethyl 2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate
• CAS: 1040075-47-5
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: OGLIXAQIGGSTCR-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  322.0±42.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetate 在 一水合肼 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 生成 2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis, antileishmanial activity and docking study of N′-substitutedbenzylidene-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazides

  摘要：

  A series of N '-substitutedbenzylidene-2-(6,7-dihydrothieno[ 3,2-c] pyridin-5(4H)-yl) acetohydrazide derivatives is synthesized and evaluated for antileishmanial activity against Leishmania donovani promastigotes. Compounds 9a and 9i were shown significant antileishmanial when compared with standard sodium stilbogluconate. Antimicrobial study revealed that compound 9b has potent as well as broad spectrum antibacterial activity when compared with ampicillin and compound 9e showed promising antifungal activity when compared with miconazole. Also, none of the synthesized compounds showed cytotoxicity up to tested concentration. Further, docking study against pteridine reductase 1 enzyme of L. donovani showed good binding interactions. ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.035
• 作为产物：
  描述：

  4,5,6,7-四氢噻吩[3,2-c]吡啶盐酸盐 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 ethyl 2(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetate
  参考文献：
  名称：

  通过交流频率控制选择性胺官能化的一或二电子氧化

  摘要：

  在这里，我们报告了一种独特的电合成方法，该方法能够选择性地单电子氧化叔胺，以生成α-氨基自由基中间体，而不是双电子氧化为亚胺阳离子，通过简单地施加最佳交流电（AC ） 频率。更重要的是，我们从循环伏安研究中发现了一种电化学描述符，可以预测各种胺底物的最佳交流频率，从而避免了优化反应条件的耗时的试错方法。交流电解的这一新发展为解决合成有机化学中具有挑战性的化学选择性问题提供了一种替代策略。

  DOI：

  10.1021/jacs.2c02605

文献信息

• Oxidative α-Trichloromethylation of Tertiary Amines: An Entry to α-Amino Acid Esters
  作者：Changming Xu、Zhaobin Zhu、Yongchang Wang、Zhiguo Jing、Bin Gao、Li Zhao、Wen-Kui Dong

  DOI：10.1021/acs.joc.8b03238

  日期：2019.2.15

  α-Trichloromethylation of tertiary amines with trimethyl(trichloromethyl)silane by oxidative coupling, using DDQ as an oxidant, has been realized. The reaction is instantaneous, is scalable, and tolerates a broad range of functional groups and heteroarenes. The trichloromethylated products can be easily converted into β,β-dichloroamines, enamines, and α-amino acid esters under operationally simple conditions

  以DDQ为氧化剂，通过氧化偶合实现了叔胺与三甲基（三氯甲基）硅烷的α-三氯甲基化反应。该反应是瞬时的，可扩展的，并且耐受广泛的官能团和杂芳烃。在操作简单的条件下，三氯甲基化的产物可以轻松地转化为β，β-二氯胺，烯胺和α-氨基酸酯。该方法为有毒的氰化反应提供了一种有效的替代方法，用于合成羧酸及其衍生物。
• Synthesis, docking and ADMET prediction of novel 5-((5-substituted-1-H-1,2,4-triazol-3-yl) methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine as antifungal agents
  作者：Jaiprakash N. Sangshetti、Firoz A. Kalam Khan、Rashmi S. Chouthe、Manoj G. Damale、Devanand B. Shinde

  DOI：10.1016/j.cclet.2014.04.003

  日期：2014.7

  A novel series of 5-((5-substituted-1H-1,2,4-triazol-3-yl)methyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridines 5(a-i) has been synthesized from thienopyridine hydrazide, substituted aromatic nitriles using 4-dimethylaminopyridine (DMAP) as a catalyst under microwave irradiation and evaluated for their in vitro antifungal activity. Compound 5g is found to be more potent against Candida albicans when compared with miconazole. Docking study of the newly synthesized compounds was performed, and results showed good binding mode in the active site of fungal enzyme P450 cytochrome lanosterol 14 alpha-demethylase. ADMET properties of synthesized compounds were also analyzed and showed good drug like properties. The results of in vitro antifungal activity, docking study and ADMET prediction revealed that the synthesized compounds have potential antifungal activity and can be further optimized and developed as a lead compound. (C) 2014 Jaiprakash N. Sangshetti. Published by Elsevier B.V.
• Synthesis, antileishmanial activity and docking study of N′-substitutedbenzylidene-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazides
  作者：Jaiprakash N. Sangshetti、Rehan I. Shaikh、Firoz A. Kalam Khan、Rajendra H. Patil、Sayali D. Marathe、Wasudev N. Gade、Devanand B. Shinde

  DOI：10.1016/j.bmcl.2014.01.035

  日期：2014.3

  A series of N '-substitutedbenzylidene-2-(6,7-dihydrothieno[ 3,2-c] pyridin-5(4H)-yl) acetohydrazide derivatives is synthesized and evaluated for antileishmanial activity against Leishmania donovani promastigotes. Compounds 9a and 9i were shown significant antileishmanial when compared with standard sodium stilbogluconate. Antimicrobial study revealed that compound 9b has potent as well as broad spectrum antibacterial activity when compared with ampicillin and compound 9e showed promising antifungal activity when compared with miconazole. Also, none of the synthesized compounds showed cytotoxicity up to tested concentration. Further, docking study against pteridine reductase 1 enzyme of L. donovani showed good binding interactions. ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates. (C) 2014 Elsevier Ltd. All rights reserved.
• Controlling One- or Two-Electron Oxidation for Selective Amine Functionalization by Alternating Current Frequency
  作者：Disni Gunasekera、Jyoti P. Mahajan、Yanick Wanzi、Sachini Rodrigo、Wei Liu、Ting Tan、Long Luo

  DOI：10.1021/jacs.2c02605

  日期：2022.6.8

  Here, we report a unique electrosynthetic method that enables the selective one-electron oxidation of tertiary amines to generate α-amino radical intermediates over two-electron oxidation to iminium cations, providing easy access to arylation products by simply applying an optimal alternating current (AC) frequency. More importantly, we have discovered an electrochemical descriptor from cyclic voltammetry

  在这里，我们报告了一种独特的电合成方法，该方法能够选择性地单电子氧化叔胺，以生成α-氨基自由基中间体，而不是双电子氧化为亚胺阳离子，通过简单地施加最佳交流电（AC ） 频率。更重要的是，我们从循环伏安研究中发现了一种电化学描述符，可以预测各种胺底物的最佳交流频率，从而避免了优化反应条件的耗时的试错方法。交流电解的这一新发展为解决合成有机化学中具有挑战性的化学选择性问题提供了一种替代策略。