thiacyclotridecane-3,12-dione | 857748-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thiacyclotridecane-3,12-dione
• 英文别名: Thiacyclotridecan-3,12-dion
• CAS: 857748-19-7
• 化学式: C₁₂H₂₀O₂S
• 分子量: 228.356
• InChiKey: FRPRKNPFEBEMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thiacyclotridecane-3,12-dione 在 盐酸肼 、 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 二乙二醇 为溶剂， 反应 0.5h， 生成
  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 作用下， 以 乙醚 、 苯 为溶剂， 生成 thiacyclotridecane-3,12-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

• Bacchetti; Canonica, Gazzetta Chimica Italiana, 1952, vol. 82, p. 243,247
  作者：Bacchetti、Canonica

  DOI：——

  日期：——
• 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.