methyl 2-((3-formylquinolin-2-yl)thio)acetate | 51925-43-0

• 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: methyl 2-((3-formylquinolin-2-yl)thio)acetate
• 英文别名: methyl [(3-formylquinolin-2-yl)thio]acetate；(3-formyl-quinolin-2-ylsulfanyl)-acetic acid methyl ester；3-Formyl-2-methoxycarbonylmethylthiochinolin；Methyl 2-[(3-formyl-2-quinolinyl)sulfanyl]acetate；methyl 2-(3-formylquinolin-2-yl)sulfanylacetate
• CAS: 51925-43-0
• 化学式: C₁₃H₁₁NO₃S
• mdl: MFCD02571247
• 分子量: 261.301
• InChiKey: ULTIVBXKOSGFSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  81.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-((3-formylquinolin-2-yl)thio)acetate 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 二苯醚 、 联苯 为溶剂， 反应 4.0h， 生成 噻吩并[2,3-b]喹啉
  参考文献：
  名称：

  Hull,R., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2911 - 2914

  摘要：

  DOI：
• 作为产物：
  描述：

  3-formyl-2-mercaptoquinoline 在 potassium carbonate 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 methyl 2-((3-formylquinolin-2-yl)thio)acetate
  参考文献：
  名称：

  Chemistry of Substituted Quinolines: Thieno[2,3- b ] and Thiopyrano[2,3- b ]quinolines

  摘要：

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500601088846

文献信息

• Synthesis of 2,3-Dihydrothieno(2,3-<i>b</i>)quinolines and Thieno(2,3-<i>b</i>)- quinolines via an Unexpected Domino Aza-MBH/Alkylation/Aldol Reaction
  作者：Pei-Shun Wei、Meng-Xue Wang、Dong-Cheng Xu、Jian-Wu Xie

  DOI：10.1021/acs.joc.5b02369

  日期：2016.2.5

  An efficient, mild, and convenient method for the preparation of 2,3-dihydrothieno(2,3-b)quinolines and thieno(2,3-b)-quinolines via an unexpected domino aza-Morita–Baylis–Hillman/alkylation/aldol reaction has been developed. The plausible mechanisms for the unexpected reaction are also given.

  2,3-二氢噻吩并（2,3-的制备一种有效的，轻度，和方便的方法b）喹啉和噻吩并（2,3- b）通过一个意想不到的多米诺氮杂森田-的Baylis-希尔曼/烷基化/烷基-quinolines醛醇缩合反应已得到发展。还给出了意外反应的合理机制。
• Hull,R., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2911 - 2914
  作者：Hull,R.

  DOI：——

  日期：——
• Chemistry of Substituted Quinolines: Thieno[2,3-<b> <i>b</i> </b>] and Thiopyrano[2,3-<b> <i>b</i> </b>]quinolines
  作者：Balaji M. Kiran、Belalakatte P. Nandeshwarappa、Vijayavittala P. Vaidya、Kittappa M. Mahadevan

  DOI：10.1080/10426500601088846

  日期：2007.3.15

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.