1,11-dibromododecane-2,10-dione | 91250-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,11-dibromododecane-2,10-dione
• 英文别名: 1,11-Dibrom-undecandion-(2,10)；1,11-Dibrom-undecan-2,10-dion；1,11-dibromo-undecane-2,10-dione；1,11-Dibromo-2,10-undecanedione；1,11-dibromoundecane-2,10-dione
• CAS: 91250-99-6
• 化学式: C₁₁H₁₈Br₂O₂
• 分子量: 342.071
• InChiKey: RFYJXARUZDWHPU-UHFFFAOYSA-N

物化性质

• 熔点：
  67.5-68.0 °C
• 沸点：
  416.3±30.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  15.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,11-dibromododecane-2,10-dione 在 sodium sulfide 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 生成 [9](2,5)-thiophenophane-1,9-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：

  壬二酰氯 在 氢溴酸 作用下， 以 乙醚 为溶剂， 生成 1,11-dibromododecane-2,10-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

• Bis[1H-imidazol-4(5)-yl]alkanes and 1,2,9,10- and 1,2,11,12-Tetraaminoalkane Tetrahydrochlorides
  作者：Bernhard Miller、Janina Altman、Wolfgang Beck

  DOI：10.1055/s-1997-4464

  日期：1997.3

  Bis[1H-imidazol-4(5)-yl]alkanes (n = 4-8) have been prepared by modified Bredereck cyclization of α,ω-dibromomethylalkanediones in formamide at 180°C. They undergo ring-cleavage acylation with methyl chloroformate to a mixture of N-formylated bis(enedicarbamates). Subsequent removal of formyl groups, reduction with palladium on charcoal and hydrolysis afford α,β,ω-1,ω-tetraaminoalkane tetrahydrochlorides.

  双[1H-咪唑-4(5)-基]烷烃（n = 4-8）是通过δ,Ï-二溴甲基烷二酮在甲酰胺中于 180°C 下的改良布雷德里克环化反应制备的。它们与氯甲酸甲酯发生环切酰化反应，生成 N-甲酰化双（烯二甲酸酯）混合物。随后除去甲酰基，在木炭上用钯还原并水解，得到 δ±,δ²,Ï-1,Ï-四氨基烷四盐酸盐。
• Fahr,E., Justus Liebigs Annalen der Chemie, 1960, vol. 638, p. 1 - 32
  作者：Fahr,E.

  DOI：——

  日期：——
• Schubert,H. et al., Journal fur praktische Chemie (Leipzig 1954), 1964, vol. 24, p. 132 - 142
  作者：Schubert,H. et al.

  DOI：——

  日期：——