[10](2,5)-thiophenophane-1,10-dione | 909869-13-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [10](2,5)-thiophenophane-1,10-dione
• 英文别名: 15-Thiabicyclo[10.2.1]pentadeca-1(14),12-diene-2,11-dione
• CAS: 909869-13-2
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: SJNCSCDDQRSNOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [10](2,5)-thiophenophane-1,10-dione 在 氢氧化钾 、 盐酸肼 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 1.5h， 生成 [10](2,5)-thiophenophane
  参考文献：
  名称：

  A New General Route to Thiophenophanes:  Synthesis and Properties of [n](2,5)Thiophenophane-1,n-diones

  摘要：

  A series of [ n]( 2,5) thiophenophane-1, n-diones ( 5) ( n = 9, 10, 12, 14, 16, and 20) were synthesized in a simple four-step route starting from the appropriate 1,omega-oligomethylenedicarboxylic acids. The bis-( halomethylketones) ( 6), which were obtained by successive treatment of the diacids with SOCl2, diazomethane, and HBr or HCl, were cyclized by Na2S under high dilution conditions. The obtained monomeric cyclic diketosulfides ( 4) were condensed with glyoxal in MeOH by slowly adding dilute NaOMe affording 5. The thiophene-2,5-dicarbonyl moiety of 5 ( n = 9) is significantly deformed as shown by X-ray crystallography, and the effect of the strain is reflected in the C=O stretching frequencies and the pi-pi* and the n-pi* absorptions.

  DOI：

  10.1021/jo060889n
• 作为产物：
  描述：

  1,12-bis-diazo-dodecane-2,11-dione 在 盐酸 、 sodium sulfide 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 生成 [10](2,5)-thiophenophane-1,10-dione
  参考文献：
  名称：

  A New General Route to Thiophenophanes:  Synthesis and Properties of [n](2,5)Thiophenophane-1,n-diones

  摘要：

  A series of [ n]( 2,5) thiophenophane-1, n-diones ( 5) ( n = 9, 10, 12, 14, 16, and 20) were synthesized in a simple four-step route starting from the appropriate 1,omega-oligomethylenedicarboxylic acids. The bis-( halomethylketones) ( 6), which were obtained by successive treatment of the diacids with SOCl2, diazomethane, and HBr or HCl, were cyclized by Na2S under high dilution conditions. The obtained monomeric cyclic diketosulfides ( 4) were condensed with glyoxal in MeOH by slowly adding dilute NaOMe affording 5. The thiophene-2,5-dicarbonyl moiety of 5 ( n = 9) is significantly deformed as shown by X-ray crystallography, and the effect of the strain is reflected in the C=O stretching frequencies and the pi-pi* and the n-pi* absorptions.

  DOI：

  10.1021/jo060889n

文献信息

• A New General Route to Thiophenophanes:  Synthesis and Properties of [<i>n</i>](2,5)Thiophenophane-1,<i>n</i>-diones
  作者：Yuji Miyahara

  DOI：10.1021/jo060889n

  日期：2006.8.1

  A series of [ n]( 2,5) thiophenophane-1, n-diones ( 5) ( n = 9, 10, 12, 14, 16, and 20) were synthesized in a simple four-step route starting from the appropriate 1,omega-oligomethylenedicarboxylic acids. The bis-( halomethylketones) ( 6), which were obtained by successive treatment of the diacids with SOCl2, diazomethane, and HBr or HCl, were cyclized by Na2S under high dilution conditions. The obtained monomeric cyclic diketosulfides ( 4) were condensed with glyoxal in MeOH by slowly adding dilute NaOMe affording 5. The thiophene-2,5-dicarbonyl moiety of 5 ( n = 9) is significantly deformed as shown by X-ray crystallography, and the effect of the strain is reflected in the C=O stretching frequencies and the pi-pi* and the n-pi* absorptions.