dimethyl 2,2'-bithiophene-3,3'-dicarboxylate | 91570-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: dimethyl 2,2'-bithiophene-3,3'-dicarboxylate
• 英文别名: [2,2']bithienyl-3,3'-dicarboxylic acid dimethyl ester；[2,2']Bithienyl-3,3'-dicarbonsaeure-dimethylester；3,3'-Dimethoxycarbonyl-bithienyl-(2.2')；Methyl 2-(3-methoxycarbonylthiophen-2-yl)thiophene-3-carboxylate
• CAS: 91570-39-7
• 化学式: C₁₂H₁₀O₄S₂
• 分子量: 282.341
• InChiKey: FUARHRSZRUSUQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2'-bithiophene-3,3'-dicarboxylate 在 氢氧化钾 作用下， 生成 2,2'-bithiophene-3,3'-dicarboxylic acid
  参考文献：
  名称：

  Studies on the Chemistry of Heterocyclics. XVIII. Mixed Bi-Aromatics I. The Synthesis and Resolution of 2-(6-Methyl-2-Nitrophenyl)-3-Thenoic Acid

  摘要：

  DOI：

  10.1021/jo50006a007
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 四氢呋喃 、 正丁基锂 作用下， 生成 dimethyl 2,2'-bithiophene-3,3'-dicarboxylate
  参考文献：
  名称：

  Gronowitz, Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1393

  摘要：

  DOI：

文献信息

• Synthesis and Solid-State Structures of Dimethyl 2,2‘-Bithiophenedicarboxylates
  作者：Martin Pomerantz、Ananda S. Amarasekara、H. V. Rasika Dias

  DOI：10.1021/jo020307b

  日期：2002.10.1

  The syntheses of dimethyl 2,2'-bithiophene-4,4'-dicarboxylate (3), dimethyl 2,2'-bithiophene-3,4'-dicarboxylate (4), and dimethyl 2,2'-bithiophene-3,3'-dicarboxylate (5) are described. Single-crystal X-ray structural analysis of these compounds shows that the thiophene rings in 3 and 4 are nearly coplanar (dihedral angle close to 0degrees) and they adopt the anti sulfur conformation in the solid state. Further, the structure of 4 is in agreement with our previous suggestion that there is an electrostatic stabilization of the planar structure due to attraction of the 3-carbonyl oxygen to the sulfur of the distal ring. In 5, however, the thiophene rings are nearly perpendicular (dihedral angle 75degrees), indicating considerable steric hindrance between the two large ester groups at the 3- and 3'-positions. Unlike compounds 3 and 4, where the thiophene rings have the sulfur atoms anti, the sulfur atoms in 5 are completely syn. This is the first instance where a bithiophene has been shown to adopt a conformation where the sulfur atoms are completely syn. The solid-state conformations of 3, 4, and 5 are in agreement with ab initio theoretical calculations on these compounds; particularly, the planar conformations of 3 and 4 reflect the previously calculated low rotation barriers of these molecules.
• Gronowitz, Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1393
  作者：Gronowitz

  DOI：——

  日期：——
• Studies on the Chemistry of Heterocyclics. XVIII. Mixed Bi-Aromatics I. The Synthesis and Resolution of 2-(6-Methyl-2-Nitrophenyl)-3-Thenoic Acid
  作者：Louis J. Owen、F. F. Nord

  DOI：10.1021/jo50006a007

  日期：1951.12