3,4-dineopentylthiophene | 156222-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,4-dineopentylthiophene
• 英文别名: 3,4-Bis(2,2-dimethylpropyl)thiophene
• CAS: 156222-93-4
• 化学式: C₁₄H₂₄S
• 分子量: 224.411
• InChiKey: LATVIEVNLJVORP-UHFFFAOYSA-N

物化性质

• 沸点：
  275.5±9.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-dineopentylthiophene 在 间氯过氧苯甲酸 作用下， 以68%的产率得到3,4-dineopentylthiophene 1,1-dioxide
  参考文献：
  名称：

  在相邻位置带有两个新戊基的芳族化合物的一般合成

  摘要：

  从甲基新戊基酮开始，以良好的总产率合成了3,4-二戊基噻吩（4）。3,4-Dineopentylthiophene-1,1-dioxide（5a）易于通过4的氧化而制得，它与各种炔属二烯亲二烯物或其等价物进行Diels-Alder反应，以提供在相邻位置带有两个新戊基的芳香族化合物。

  DOI：

  10.1016/s0040-4039(00)77012-2
• 作为产物：
  描述：

  3,4-Bis(2,2-dimethylpropyl)thiolane-3,4-diol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.5h， 以90%的产率得到3,4-dineopentylthiophene
  参考文献：
  名称：

  Preparation of Congested Thiophenes Carrying Bulky Substituents on the 3- and 4-Positions and Their Conversion to the Benzene Derivatives

  摘要：

  Highly congested thiophenes, 3,4-di-tert-butyl-, 3,4-di(1-adamantyl)-, 3,4-dineopentyl-, and 3-(1-adamantyl)-4-tert-butylthiophenes (4a-d), were prepared in satisfactory overall yields by intramolecular reductive coupling of 3-thiapentane-1,5-diones (1a-d) followed by acid-catalyzed dehydration of the resulting thiolane-3,4-diols (2a-d). Experimental procedures of this; thiophene synthesis are fully described. Oxidation of the thiophenes 4a-d with m-CPBA gave the corresponding thiophene 1,1-dioxides 13a-d in good yields. The Diels-Alder reactions of 13a-d with phenyl vinyl sulfone gave o-di-tert-butyl-, o-di(1-adamantyl)-, o-dineopentyl-, and o-(1-adamantyl)-tert-butylbenzenes (17a-d) directly in high yields with loss of benzenesulfinic acid and sulfur dioxide. The dioxides 13a-d also underwent Diels-Alder reactions with alkynic dienophiles to give the corresponding benzene derivatives carrying two bulky substituents on adjacent positions. Pyridazines 25b,c, carrying bulky substituents on the 4- and 5-positions, were also synthesized through Diels-Alder reaction of 13b,c with PTAD. Dimethylation of the 2- and 5-positions of 13a-d was attained by treatment with strong bases followed by reactions with methyl iodide. The resulting tetrasubstituted thiophene 1,1-dioxides 14a-d reacted with DMAD to give highly congested hexasubstituted benzene derivatives 15a-d in good yields. Finally, structural features of the congested molecules are discussed on the basis of NMR analyses. Typically, the barriers to rotation (Delta H double dagger) about the benzene to the bulky substituents of 15a,c,d were determined to be 8.59, 15.3, and 7.40 kcal/mol, respectively, by NMR total line-shape analysis.

  DOI：

  10.1021/jo971710z

文献信息

• Synthesis and Characterization of Thiophene 1-Oxides Kinetically Stabilized by Bulky Substituents at the 3- and 4-Positions
  作者：Juzo Nakayama、Ting Yu、Yoshiaki Sugihara、Akihiko Ishii

  DOI：10.1246/cl.1997.499

  日期：1997.6

  Oxidation of 3,4-di-t-butyl- and 3,4-di-1-adamantyl-, and 2,4-di-t-butylthiophenes with an equimolar amount of m-chloroperbenzoic acid in the presence of BF3•Et2O gave the corresponding thiophene 1-oxides in good yields, which are stable enough to be isolated in pure crystalline form. An X-ray single crystal structure analysis led to the conclusion that thiophene 1-oxides would not be aromatic.

  在 BF3•Et2O 存在下用等摩尔量的间氯过苯甲酸氧化 3,4-二叔丁基和 3,4-二-1-金刚烷基和 2,4-二叔丁基噻吩以良好的产率得到相应的噻吩 1-氧化物，其足够稳定，可以以纯结晶形式分离。X 射线单晶结构分析得出的结论是，噻吩 1-氧化物不是芳香族化合物。
• Nakayama Juzo, Yoshimura Koichi, Tetrahedron Lett, 35 (1994) N 17, S 2709-2712
  作者：Nakayama Juzo, Yoshimura Koichi

  DOI：——

  日期：——