thiacycloheptadecane-3,16-dione | 408310-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thiacycloheptadecane-3,16-dione
• 英文别名: Thiacycloheptadecan-3,16-dion
• CAS: 408310-57-6
• 化学式: C₁₆H₂₈O₂S
• 分子量: 284.463
• InChiKey: SOBJKRMDVRQEMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  草酸醛 、 thiacycloheptadecane-3,16-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以54.1%的产率得到[14](2,5)-thiophenophane-1,14-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
• 作为产物：
  描述：

  十四烷二酸 在 盐酸 、 sodium sulfide 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 thiacycloheptadecane-3,16-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：——