3,4-dibenzyl-2,5-dimethylthiophene | 91377-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dibenzyl-2,5-dimethylthiophene
• 英文别名: 3,4-Dibenzyl-2,5-dimethyl-thiophen
• CAS: 91377-93-4
• 化学式: C₂₀H₂₀S
• 分子量: 292.445
• InChiKey: DDJBGPQXEWCNCR-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  410.4±14.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dibenzyl-2,5-dimethylthiophene 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 生成 2,5-dimethyl-3,4-bis(phenylmethyl)thiophene S-oxide
  参考文献：
  名称：

  从噻吩S-氧化物到 7-噻二环[2.2.1]庚-5-烯

  摘要：

  具有 7-硫双环 [2.2.1]hept-5-ene 单元的低聚环已通过噻吩 S-氧化物与烯烃的环加成反应立体选择性制备，随后用 PBr3 对环加合物的磺氧基桥进行脱氧。

  DOI：

  10.3184/030823409x12562932030738
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 盐酸 、 三氯化铝 、 苯 作用下， 生成 3,4-dibenzyl-2,5-dimethylthiophene
  参考文献：
  名称：

  Gol'dfarb; Kondakowa, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1956, p. 495,498; engl. Ausg. S. 487, 489

  摘要：

  DOI：

文献信息

• Lewis Acid Catalysis in the Oxidative Cycloaddition of Thiophenes¹
  作者：Yuanqiang Li、Thies Thiemann、Tsuyoshi Sawada、Shuntaro Mataka、Masashi Tashiro

  DOI：10.1021/jo961985z

  日期：1997.11.1

  Thiophenes 1 were treated with m-chloroperbenzoic acid (m-CPBA) under BF3 . Et2O catalysis to afford thiophene S-monoxides. These could be reacted in situ as intermediary species with a number of dienophiles to provide arenes (with alkynes as dienophiles) or 7-thiabicyclo[2.2.1]hept-2-ene 7-oxides (with alkenes as dienophiles). It was also possible to isolate thiophene S-monoxides in solution and to cycloadd them in a second step. In either way it could be shown that the use of BF3 . Et2O enhances the yields of the oxidative cycloaddition of thiophenes considerably. Moreover a greater variety of dienophiles (29a, 29b, 29c) could be reacted with thiophenes than in the case of the noncatalyzed reaction. All cycloadditions catalyzed by BF3 . Et2O give only a single diastereoisomer as cycloadduct. The reactions show a high pi-facial selectivity, a fact that can be explained by the Cieplak-effect. Without added dienophiles, 2-methylthiophene (le) gave a single dimer (36) of 2-methylthiophene S-monoxide, whereas 2,5-dimethylthiophene (la) gave three dimers (32a-c). In the case of tetrasubstituted thiophenes, thiophene S-monoxides (e.g., 31b and 31c) could be isolated in substance.
• Photochemical and electrochemical behavior of thiophene-S-oxides
  作者：Thies Thiemann、Daisuke Ohira、Kazuya Arima、Tsuyoshi Sawada、Shuntaro Mataka、Frank Marken、Richard G. Compton、Steven D. Bull、Stephen G. Davies

  DOI：10.1002/1099-1395(200010)13:10<648::aid-poc290>3.0.co;2-t

  日期：2000.10

  The photochemical and electrochemical behavior of thiophene-S-oxides as a class was studied for the first time. It was shown that in both cases deoxygenation of the S-O functionality takes place. The outcome of the photoirradiation is very dependent on the substituent pattern of the starting material. Thiophene-S-oxides show different reduction behaviors in presence and absence of proton donors. In the absence of proton donors the reduction potential of the compounds is dependent on the substituents of the molecules. In the presence of proton donors, the substituents play a less significant role and a number of thiophene-S-oxides were reduced electrochemically to the corresponding thiophenes in presence of a 10-fold excess of benzoic acid. Copyright (C) 2000 John Wiley & Sons, Ltd.
• KONAR, A., CHEM. SCR., 1984, 23, N 2, 53-63
  作者：KONAR, A.

  DOI：——

  日期：——
• From thiophene <i>S</i>-oxides to 7-thiabicyclo[2.2.1]hept-5-enes
  作者：Yuan-Qiang Li、Carolin Thiemann、Daisuke Ohira、Shuntaro Mataka、Masashi Tashiro、Thies Thiemann

  DOI：10.3184/030823409x12562932030738

  日期：2009.11

  Oligocycles with a 7-thiabicyclo[2.2.1]hept-5-ene unit have been prepared stereoselectively by cycloaddition of thiophene S-oxides to alkenes and subsequent deoxygenation of the sulfoxy bridge of the cycloadducts with PBr3.

  具有 7-硫双环 [2.2.1]hept-5-ene 单元的低聚环已通过噻吩 S-氧化物与烯烃的环加成反应立体选择性制备，随后用 PBr3 对环加合物的磺氧基桥进行脱氧。
• Gol'dfarb; Kondakowa, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1956, p. 495,498; engl. Ausg. S. 487, 489
  作者：Gol'dfarb、Kondakowa

  DOI：——

  日期：——