6-Bromo-3,5-dihydro-1H-thieno[3,4-c]pyrrol-4-carbaldehyd-2,2-dioxid | 313252-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: 6-Bromo-3,5-dihydro-1H-thieno[3,4-c]pyrrol-4-carbaldehyd-2,2-dioxid
• 英文别名: 4-bromo-2,2-dioxo-3,5-dihydro-1H-thieno[3,4-c]pyrrole-6-carbaldehyde
• CAS: 313252-68-5
• 化学式: C₇H₆BrNO₃S
• 分子量: 264.1
• InChiKey: XSCTVJZPHCSHII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  足球烯 、 6-Bromo-3,5-dihydro-1H-thieno[3,4-c]pyrrol-4-carbaldehyd-2,2-dioxid 以 various solvent(s) 为溶剂， 反应 5.5h， 以19.7%的产率得到3-Bromo-4,7-dihydro-2H-[5,6]fullereno-C60-I_h-[1,9-f]isoindol-1-carbaldehyd
  参考文献：
  名称：

  Synthese von Sulfolenobilinen und deren Cyclisierung zu Chlorinatozink-Fulleren-Dyaden

  摘要：

  A novel chlorinatozinc-fullerene dyad 18 was synthesized to model the photosynthetic reaction center. The synthetic key step for the formation of the dyad 18 is an unusual one-pot reaction of the (sulfolenobilinato) nickel rac-16a,b with concomitant generation of the chlorin macrocycle and linkage to the [5,6]fullerene-C-60-I-h. This one-pot reaction is a complex cascade of single reaction steps with a total yield of 32% and an average yield of 83% for the individual steps. The chlorinatozinc-fullerene dyad is so far one of three examples that contain chlorin moieties, the chromophores in naturally occurring photosynthetic systems.

  DOI：

  10.1002/1522-2675(20000906)83:9<2231::aid-hlca2231>3.0.co;2-s
• 作为产物：
  描述：

  3,5-Dihydro-1H-thieno[3,4-c]pyrrolcarbonsaeure-benzylester 在 palladium on activated charcoal 氢气 、 pyridinium hydrobromide perbromide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 6-Bromo-3,5-dihydro-1H-thieno[3,4-c]pyrrol-4-carbaldehyd-2,2-dioxid
  参考文献：
  名称：

  Synthese von Sulfolenobilinen und deren Cyclisierung zu Chlorinatozink-Fulleren-Dyaden

  摘要：

  A novel chlorinatozinc-fullerene dyad 18 was synthesized to model the photosynthetic reaction center. The synthetic key step for the formation of the dyad 18 is an unusual one-pot reaction of the (sulfolenobilinato) nickel rac-16a,b with concomitant generation of the chlorin macrocycle and linkage to the [5,6]fullerene-C-60-I-h. This one-pot reaction is a complex cascade of single reaction steps with a total yield of 32% and an average yield of 83% for the individual steps. The chlorinatozinc-fullerene dyad is so far one of three examples that contain chlorin moieties, the chromophores in naturally occurring photosynthetic systems.

  DOI：

  10.1002/1522-2675(20000906)83:9<2231::aid-hlca2231>3.0.co;2-s

文献信息

• Synthese von Sulfolenobilinen und deren Cyclisierung zu Chlorinatozink-Fulleren-Dyaden
  作者：Olaf Kutzki、Andreas Walter、Franz-Peter Montforts

  DOI：10.1002/1522-2675(20000906)83:9<2231::aid-hlca2231>3.0.co;2-s

  日期：2000.9.6

  Synthesis of Sulfolenobilins and Their Cyclization Directed to Chlorinatozinc-Fullerene Dyads A novel chlorinatozinc-fullerene dyad 18 was synthesized to model the photosynthetic reaction center. The synthetic key step for the formation of the dyad 18 is an unusual one-pot reaction of the (sulfolenobilinato)nickel rac-16a,b with concomitant generation of the chlorin macrocycle and linkage to the [5