5,6,11,12-tetrahydrodibenzo[c,g][1,2]diazocine-2-carbonitrile | 1400887-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5,6,11,12-tetrahydrodibenzo[c,g][1,2]diazocine-2-carbonitrile
• 英文别名: 5,6,11,12-Tetrahydrobenzo[c][1,2]benzodiazocine-2-carbonitrile
• CAS: 1400887-67-3
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: PTUFOXIWGBHFLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6,11,12-tetrahydrodibenzo[c,g][1,2]diazocine-2-carbonitrile 在 titanium(III) chloride 、 氢溴酸 、 双氧水 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 11,12-dihydrodibenzo[c,g][1,2]diazocine-2-carboxylic acid
  参考文献：
  名称：

  Incorporation of cyclic azobenzene into oligodeoxynucleotides for the photo-regulation of DNA hybridization

  摘要：

  Cyclic azobenzene carboxylic acid was synthesized using a shortened route. After reaction with D-threolinol, the resulting cyclic azobenzene-D-threolinol (cAB-Thr) building block was transformed into the corresponding DMTr-protected phosphoramidite, and incorporated into oligodeoxynucleotides at various positions and frequencies by solid phase synthesis. The melting temperatures of these modified oligonucleotides were determined by UV spectrometry. Photo-regulation of cAB-Thr-modified oligonucleotides with their complementary sequence was evaluated by Fluorescence Resonance Energy Transfer experiments using a fluorescein-Black Hole Quencher pair. Results suggest that while cis-cAB destabilizes DNA duplexes, trans-cAB can be accommodated in double stranded DNA. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.043
• 作为产物：
  描述：

  2-bromo-11,12-dihydrodibenzo[c,g][1,2]diazocine-6-oxide 在 氢化铝 、 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5,6,11,12-tetrahydrodibenzo[c,g][1,2]diazocine-2-carbonitrile
  参考文献：
  名称：

  Incorporation of cyclic azobenzene into oligodeoxynucleotides for the photo-regulation of DNA hybridization

  摘要：

  Cyclic azobenzene carboxylic acid was synthesized using a shortened route. After reaction with D-threolinol, the resulting cyclic azobenzene-D-threolinol (cAB-Thr) building block was transformed into the corresponding DMTr-protected phosphoramidite, and incorporated into oligodeoxynucleotides at various positions and frequencies by solid phase synthesis. The melting temperatures of these modified oligonucleotides were determined by UV spectrometry. Photo-regulation of cAB-Thr-modified oligonucleotides with their complementary sequence was evaluated by Fluorescence Resonance Energy Transfer experiments using a fluorescein-Black Hole Quencher pair. Results suggest that while cis-cAB destabilizes DNA duplexes, trans-cAB can be accommodated in double stranded DNA. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.043

文献信息

• Synthesis of cyclic azobenzene analogues
  作者：Dhruval K. Joshi、Matthew J. Mitchell、Doug Bruce、Alan J. Lough、Hongbin Yan

  DOI：10.1016/j.tet.2012.06.007

  日期：2012.10

  formate buffer gave a cyclic azoxybenzene, 11,12-dihydrodibenzo[c,g][1,2]diazocine-5-oxide. The latter compound was converted into cyclic azobenzene and analogues (chloro-, bromo-, and cyano-) through subsequent transformations. Hydrolysis of the cyano cyclic azobenzene gave the corresponding carboxylic acid. This carboxylic acid was finally reacted with d-threoninol to give the corresponding amide, which

  在碱性三乙基甲酸铵缓冲液存在下，2,2'-二硝基二苄基与铅金属粉末反应，得到环状a氧基苯，11,12-二氢二苯并[ c，g ] [1,2]重氮电影-5-氧化物。通过随后的转化，将后者化合物转化为环状偶氮苯和类似物（氯代，溴代和氰基）。氰基环状偶氮苯的水解得到相应的羧酸。该羧酸最后与对苏氨酸反应，得到相应的酰胺，酰胺在光照下容易发生光异构化。