dimethyl 4,5-diphenylthiophene-2,3-dicarboxylate | 3319-41-3

• 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: dimethyl 4,5-diphenylthiophene-2,3-dicarboxylate
• 英文别名: 2,3-bis(methoxycarbonyl)-4,5-diphenylthiophene；4,5-diphenyl-thiophene-2,3-dicarboxylic acid dimethyl ester；2,3-Diphenyl-4,5-dimethoxycarbonyl-thiophen；4,5-Diphenyl-2,3-carbmethoxy-thiophen
• CAS: 3319-41-3
• 化学式: C₂₀H₁₆O₄S
• 分子量: 352.411
• InChiKey: VUABOQHBVUFGEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  458.6±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二苯基乙炔 、 3,4-bis(methoxycarbonyl)-1,2-dithiete 以 对二甲苯 为溶剂， 反应 2.0h， 生成 dimethyl 4,5-diphenylthiophene-2,3-dicarboxylate
  参考文献：
  名称：

  Reaction of 1,2-Dithiete with Alkenes and Alkynes:  Experimental and Theoretical Study

  摘要：

  Reactions of 3,4-bis(methoxycarbonyl)-1,2-dithiete (1) with various alkenes or alkynes formed 2,3-dihydro-1,4-dithiins or thiophenes, respectively. The reactions with alkenes were stereospecific, which indicates the concerted reaction between 1,2-bis(methoxycarbonyl)ethane-1,2-dithione (13), the valence isomer of the 1,2-dithiete, and the dienophiles. Theoretical study confirmed the reactions of 13 with alkenes and alkynes are of reverse electron demand hetero Diels-Alder type. The MO calculations showed the 1,2-dithiete 1 was 5.8 kcal mol(-1) more stable than the corresponding ethane-1,2-dithione 13, and the tautomerization energy between the 1,2-dithiete and the ethane-1,2-dithione was also calculated to be 28.5 kcal mol(-1)from the 1,2-dithiete, which suggests the tautomerization from 1,2-dithiete 1 to ethane-1,2-dithione 13 is possible at least at high temperature. Reaction of 3,4,7,8-tetrakis(methoxycarbonyl)-1,2,5, (2) or (Z,Z,Z,Z)-3,4,7,8,1 1,12,15,16-octakis-(methoxycarbonyl)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,12-tetraene (3) with ethyl vinyl ether also formed the 2,3-dihydro-1,4-dithiin derivative, which is the same compound obtained by the reaction of 1,2-dithiete 1 with the ether. 1,2,5,6-Tetrathiocin 2 and 16-membered cyclic compound 3 also reacted with diphenylacetylene to give the thiophene derivative.

  DOI：

  10.1021/jo9908086

文献信息

• A New Simple Method for the Synthesis of Thiophene Derivatives — Generation of Thiocarbonyl Ylides form S-a-(Dimethylphenylsilyl)benzyl Acylates and Their Cycloaddition with Acetylenic Dipolarophiles —
  作者：Mitsuo Komatsu、Jinil Choi、Masatoshi Mihara、Yoji Oderaotoshi、Satoshi Minakata

  DOI：10.3987/com-02-9616

  日期：——

  The cycloaddition of S-α-(dimethylphenylsilyl)benzyl acylates (1) with acetylenic dipolarophiles via 1,4-silatropy proceeded readily to afford thiophene derivatives. The reaction of thioesters (1) with 1-diethylamino-1-propyne (A), an electron-rich acetylenic dipolarophile, gave 5-aryl-3-diethylamino-4-methyl-2-phenylthiophenes (3) and 4-aryl-2-diethylamino-3-methyl-5-phenylthiophenes (4). When dimethyl

  S-α-(二甲基苯基甲硅烷基)苄基酰化物 (1) 与炔属偶极体通过 1,4-silatropy 的环加成反应很容易得到噻吩衍生物。硫酯 (1) 与 1-二乙氨基-1-丙炔 (A)（一种富电子的炔属偶极体）反应，得到 5-芳基-3-二乙氨基-4-甲基-2-苯基噻吩 (3) 和 4-芳基- 2-二乙氨基-3-甲基-5-苯基噻吩 (4)。当使用缺电子炔烃二甲基乙炔二甲酸酯 (DMAD) 时，硫酯 (1) 的反应仅提供噻吩衍生物 (4)。
• Intramolecular carbyne-carbyne coupling on exposure of [μ3-η1-CR1][μ3-η1-CR2][CpCo]3 clusters to sulphur and selenium: A novel synthesis of 1-cobalta-2,5-diheterocyclopent-3-enes
  作者：K.P.C. Vollhardt、E.C. Walborsky

  DOI：10.1016/s0277-5387(00)86322-6

  日期：1988.1
• Reactions of Elemental Sulfur and Selenium with Some Asetylenic Compounds. Formation of Thiophenes and Selemophenes
  作者：Juzo Nakayama、Rie Yomoda、Masamatsu Hoshino

  DOI：10.3987/r-1987-08-2215

  日期：——