2-喹啉-3-乙酸乙酯 | 33054-18-1

• 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
• 中文名称: 2-喹啉-3-乙酸乙酯
• 英文名称: ethyl 2-(quinolin-3-yl) acetate
• 英文别名: quinolin-3-yl-acetic acid ethyl ester；[3]quinolyl-acetic acid ethyl ester；[3]Chinolyl-essigsaeure-aethylester；Chinolin-(3)-essigsaeureethylester；Ethyl 2-(quinolin-3-YL)acetate；ethyl 2-quinolin-3-ylacetate
• CAS: 33054-18-1
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: LETQUFNRBJEUBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-喹啉-3-乙酸乙酯 在 sodium hydroxide 、 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-Quinolin-3-yl-cyclopentanecarboxylic acid
  参考文献：
  名称：

  N-(Arylacetyl)-biphenylalanines as Potent VLA-4 Antagonists

  摘要：

  A series of potent N-(aralkyl-, arylcycloalkyl-, and heteroaryl-acyl)-4-biphenylalanine VLA-4 antagonists was prepared by rapid analogue methods using solid-phase chemistry. Further optimization led to several highly potent compounds (IC50 < 1 nM). Evaluation of rat pharmacokinetic revealed generally high clearance. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00366-9
• 作为产物：
  描述：

  3-乙酰基喹啉 在 ammonium sulfide 、 sulfur 作用下， 生成 2-喹啉-3-乙酸乙酯
  参考文献：
  名称：

  青霉素的生物合成；一些多环和杂环乙酸的N-2-羟乙基酰胺作为前体。

  摘要：

  DOI：

  10.1021/ja01189a002

文献信息

• Oxidative Cascade Reaction of<i>N</i>-Aryl-3-alkylideneazetidines and Carboxylic Acids: Access to Fused Pyridines
  作者：Wangshui Cai、Shuang Wang、Hitesh B. Jalani、Junxian Wu、Hongjian Lu、Guigen Li

  DOI：10.1021/acs.orglett.8b01427

  日期：2018.7.6

  silver-promoted oxidative cascade reaction of N-aryl-3-alkylideneazetidines with carboxylic acids is reported, providing a very efficient pathway to functionalized fused pyridines. This method allows introduction of fused pyridine ring systems to heterocycles, drugs, and natural products. A mechanistic study revealed that silver salt is essential for the chemo- and regioselective ring expansion, sequential

  据报道，N-芳基-3-亚烷基亚氮杂环丁烷与羧酸的多官能团银促进了氧化级联反应，为官能化的稠合吡啶提供了非常有效的途径。该方法允许将稠合的吡啶环系统引入杂环，药物和天然产物中。机理研究表明，银盐对于化学和区域选择性环的扩展，顺序的氧化亲核加成和氧化芳构化至关重要。该方法代表了应变的N-杂环一起经历具有π键和亲核试剂的级联反应的第一个例子。
• Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with o-Aminobenzaldehydes: Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone, and Ruteacarpine
  作者：Daniel Seidel、Matthew Richers、Indubhusan Deb、Alena Platonova、Chen Zhang

  DOI：10.1055/s-0033-1338852

  日期：——

  Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine alpha-amination/N-alkylation. This unique alpha-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.
• MAROLT V.; STANORNIK B.; TISLER M.; VERCEK B., VESTN. SLOV. KEM. DRUST., 1978, 25, NO 3, 265-271
  作者：MAROLT V.、 STANORNIK B.、 TISLER M.、 VERCEK B.

  DOI：——

  日期：——
• N-(Arylacetyl)-biphenylalanines as Potent VLA-4 Antagonists
  作者：Bing Li、Stephen E de Laszlo、Theodore M Kamenecka、Ihor E Kopka、Philippe L Durette、Thomas Lanza, Jr、Malcolm MacCoss、Sharon Tong、Richard A Mumford、Ermengilda D McCauley、Gail Van Riper、John A Schmidt、William K Hagmann

  DOI：10.1016/s0960-894x(02)00366-9

  日期：2002.8

  A series of potent N-(aralkyl-, arylcycloalkyl-, and heteroaryl-acyl)-4-biphenylalanine VLA-4 antagonists was prepared by rapid analogue methods using solid-phase chemistry. Further optimization led to several highly potent compounds (IC50 < 1 nM). Evaluation of rat pharmacokinetic revealed generally high clearance. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Biosynthesis of Penicillins. VI. N-2-Hydroxyethylamides of Some Polycyclic and Heterocyclic Acetic Acids as Precursors¹
  作者：Reuben G. Jones、Quentin F. Soper、Otto K. Behrens、Joseph W. Corse

  DOI：10.1021/ja01189a002

  日期：1948.9