4-methoxyquinoline-2-carboxylic acid ethyl ester | 24782-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methoxyquinoline-2-carboxylic acid ethyl ester
• 英文别名: ethyl 4-methoxyquinoline-2-carboxylate；Ethyl 4-methoxyquinolin-2-carboxylat；Ethyl 4-methoxyquinoline-2-carboxylate
• CAS: 24782-25-0
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: YXXYFFJMHAYWOB-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±22.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxyquinoline-2-carboxylic acid ethyl ester 在 ammonium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 4-methoxy-2-quinaldamide
  参考文献：
  名称：

  Synthesis of Perspicamide A and Related Diverse Analogues: Their Bioevaluation as Potent Antileishmanial Agents

  摘要：

  The first protocol for the synthesis of perspicamide A and related diverse analogues has been developed from economical and readily available starting materials. Furthermore, a few synthesized analogues, 24a, 246, 24c, 24d, and 241, exhibited potent activity against Leishmania donovani with IC50 values ranging from 3.75 to 10.37 mu M and a selectivity index (SI) ranging from 9.58 to 53.12, which is improved compared to the standard drug Miltefosine (IC50 12.4 mu M and SI 4.1).

  DOI：

  10.1021/jo3025626
• 作为产物：
  描述：

  diethyl 2-(phenylamino)maleate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-methoxyquinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Perspicamide A and Related Diverse Analogues: Their Bioevaluation as Potent Antileishmanial Agents

  摘要：

  The first protocol for the synthesis of perspicamide A and related diverse analogues has been developed from economical and readily available starting materials. Furthermore, a few synthesized analogues, 24a, 246, 24c, 24d, and 241, exhibited potent activity against Leishmania donovani with IC50 values ranging from 3.75 to 10.37 mu M and a selectivity index (SI) ranging from 9.58 to 53.12, which is improved compared to the standard drug Miltefosine (IC50 12.4 mu M and SI 4.1).

  DOI：

  10.1021/jo3025626

文献信息

• Alkylation of 2- and 3-alkoxycarbonyl-4-quinolinones. DFT study on the regioselectivity
  作者：María S. Shmidt、Pau Arroyo Mañez、Carlos A. Stortz、Isabel A. Perillo、Daniel Vega、María M. Blanco

  DOI：10.1016/j.molstruc.2016.08.057

  日期：2017.1

  O-alkylated products. The behavior in basic medium of compounds 1 differs from the 3-alkoxycarbonyl-4-quinolinones (4) isomers suggesting that the position of the carboxylate group determines the regioselectivity of the reaction. DFT calculations allow us to conclude that for 3-alkoxycarbonyl-4-quinolinones, the N-alkylation would be thermodynamically and kinetically favored. But for 2-alkoxycarbonyl-4-quinolinones

  摘要 2-烷氧基羰基-4-喹啉酮(1) 与多种烷基化试剂在不同条件下反应，生成相应的O-烷基化产物。化合物 1 在碱性介质中的行为不同于 3-alkoxycarbonyl-4-quinolinones (4) 异构体，表明羧酸根的位置决定了反应的区域选择性。DFT 计算使我们得出结论，对于 3-烷氧基羰基-4-喹啉酮，N-烷基化在热力学和动力学上都是有利的。但是对于 2-烷氧基羰基-4-喹啉酮，环的 2-位侧链阻止了与连续杂原子的平面近似，从而导致更有利的 O-烷基化过渡态。O-烷基化产物的晶体结构由单晶 X 射线衍射测定。
• Accessing Rare α‐Heterocyclic Aziridines via Brønsted Acid‐catalyzed Michael Addition/Annulation: Scope, Limitations, and Mechanism
  作者：Timothy A. Hilton、Andrew G. Leach、Aidan P. McKay、Allan J. B. Watson

  DOI：10.1002/chem.202303993

  日期：2024.4.11

  We report an approach to the diastereoselective synthesis of rare 1,2-disubstituted heterocyclic aziridines. Our approach utilizes an inherent degradation of 1,2-chloroamines in the presence of trace acid, followed by annulation to give a diverse array of cis-aziridines which are not captured by alternative synthetic methodologies. The scope, limitations, and mechanistic insights into the selectivity

  我们报告了一种稀有 1,2-二取代杂环氮丙啶的非对映选择性合成方法。我们的方法利用 1,2-氯胺在微量酸存在下的固有降解，然后环化，得到多种顺式氮丙啶，而其他合成方法无法捕获这些顺式氮丙啶。介绍了选择性的范围、局限性和机制见解。
• Synthesis of Perspicamide A and Related Diverse Analogues: Their Bioevaluation as Potent Antileishmanial Agents
  作者：Anand Kumar Pandey、Rashmi Sharma、Rahul Shivahare、Ashish Arora、Neeraj Rastogi、Suman Gupta、Prem M. S. Chauhan

  DOI：10.1021/jo3025626

  日期：2013.2.15

  The first protocol for the synthesis of perspicamide A and related diverse analogues has been developed from economical and readily available starting materials. Furthermore, a few synthesized analogues, 24a, 246, 24c, 24d, and 241, exhibited potent activity against Leishmania donovani with IC50 values ranging from 3.75 to 10.37 mu M and a selectivity index (SI) ranging from 9.58 to 53.12, which is improved compared to the standard drug Miltefosine (IC50 12.4 mu M and SI 4.1).