Methyl 2-{[(dimethylamino)methylidene]amino}thiophene-3-carboxylate | 338750-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: Methyl 2-{[(dimethylamino)methylidene]amino}thiophene-3-carboxylate
• 英文别名: methyl 2-(dimethylaminomethylideneamino)thiophene-3-carboxylate
• CAS: 338750-40-6
• 化学式: C₉H₁₂N₂O₂S
• 分子量: 212.272
• InChiKey: KFUNYBLJEOERSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰乙酸叔丁酯 、 Methyl 2-{[(dimethylamino)methylidene]amino}thiophene-3-carboxylate 以 叔丁醇 为溶剂， 生成 methyl 2-{[(1Z)-3-tert-butoxy-2-cyano-3-oxoprop-1-en-1-yl]amino}thiophene-3-carboxylate
  参考文献：
  名称：

  A facile, scalable preparation of 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles

  摘要：

  We report a new synthesis of thieno[2,3-b]pyridine-5-carbonitriles from 2-aminothiophene-3-carboxylate esters. The key step of the synthesis is a thermally promoted elimination/decarboxylation followed by nucleophilic cyclization to give 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles. The reactions proceed in good yield and generally require no chromatographic purification. These compounds are easily transformed in two steps to 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitriles which are key intermediates in the synthesis of various kinase inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.107
• 作为产物：
  描述：

  2-氨基噻吩-3-羧酸甲酯 、 N,N-二甲基甲酰胺二甲基缩醛 生成 Methyl 2-{[(dimethylamino)methylidene]amino}thiophene-3-carboxylate
  参考文献：
  名称：

  A facile, scalable preparation of 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles

  摘要：

  We report a new synthesis of thieno[2,3-b]pyridine-5-carbonitriles from 2-aminothiophene-3-carboxylate esters. The key step of the synthesis is a thermally promoted elimination/decarboxylation followed by nucleophilic cyclization to give 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles. The reactions proceed in good yield and generally require no chromatographic purification. These compounds are easily transformed in two steps to 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitriles which are key intermediates in the synthesis of various kinase inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.107

文献信息

• A facile, scalable preparation of 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles
  作者：L. Nathan Tumey、Niala Bhagirath、Biqi Wu、Diane H. Boschelli

  DOI：10.1016/j.tetlet.2008.09.107

  日期：2008.11

  We report a new synthesis of thieno[2,3-b]pyridine-5-carbonitriles from 2-aminothiophene-3-carboxylate esters. The key step of the synthesis is a thermally promoted elimination/decarboxylation followed by nucleophilic cyclization to give 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carbonitriles. The reactions proceed in good yield and generally require no chromatographic purification. These compounds are easily transformed in two steps to 4-chloro-2-iodothieno[2,3-b]pyridine-5-carbonitriles which are key intermediates in the synthesis of various kinase inhibitors. (c) 2008 Elsevier Ltd. All rights reserved.