5-nitro-2-nitrosopyridine | 1101177-88-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-nitro-2-nitrosopyridine
• 英文别名: 5-Nitro-2-nitroso-pyridine
• CAS: 1101177-88-1
• 化学式: C₅H₃N₃O₃
• 分子量: 153.097
• InChiKey: IQLHQHNBYSTMHO-UHFFFAOYSA-N

物化性质

• 沸点：
  321.3±27.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-2-nitrosopyridine 、 麦角固醇 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到5,8-dihydro-8α,5α-(N-5-nitro-2-pyridinylepoxyimino)-ergosterol
  参考文献：
  名称：

  Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol

  摘要：

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

  DOI：

  10.1021/ol900997t
• 作为产物：
  描述：

  2-[(二甲基-lambda4-硫代)氨基]-5-硝基吡啶 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-nitro-2-nitrosopyridine
  参考文献：
  名称：

  Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol

  摘要：

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

  DOI：

  10.1021/ol900997t

文献信息

• Syntheses of New Spirocarbocyclic Nucleoside Analogs Using Iminonitroso Diels−Alder Reactions
  作者：Weimin Lin、Anuradha Gupta、Kyung Hee Kim、David Mendel、Marvin J. Miller

  DOI：10.1021/ol802553g

  日期：2009.1.15

  dienes coupled efficiently in a series of iminonitroso Diels−Alder reactions to produce a series of new spirocyclic adducts. Hydrogenolysis of these adducts afforded new spirocycles that contain multiple handles for further functionalization. Furthermore, stereocontrolled dihydroxylation and reductive cleavage of the spirocyclic adducts generated versatile scaffolds for the syntheses and derivatization

  N -Cbz-和Boc-保护的螺环二烯通过环戊二烯的二烷基化制备。这些二烯在一系列亚氨基亚硝基 Diels-Alder 反应中有效偶联，以产生一系列新的螺环加合物。这些加合物的氢解提供了新的螺环，其中包含用于进一步功能化的多个手柄。此外，螺环加合物的立体控制二羟基化和还原裂解为新型螺环碳环核苷类似物的合成和衍生化提供了多功能支架。
• Syntheses and biological evaluation of ring-C modified colchicine analogs
  作者：Baiyuan Yang、Zhiqing C. Zhu、Holly V. Goodson、Marvin J. Miller

  DOI：10.1016/j.bmcl.2010.03.056

  日期：2010.6

  Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels–Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through retro Diels–Alder reactions under the assayed conditions. In vitro microtubule polymerization

  使用亚氨基亚硝基 Diels-Alder 反应以高度区域和立体选择性的方式从秋水仙碱合成环 C 修饰的生物碱。几种类似物表现出类似于秋水仙碱本身对 PC-3 和 MCF-7 癌细胞系的细胞毒活性，通过在测定条件下通过逆狄尔斯-阿尔德反应作为秋水仙碱的前药。体外微管聚合试验表明这些修饰影响了它们与微管蛋白的相互作用。
• Regioselective annulation of nitrosopyridine with alkynes: straightforward synthesis of N-oxide-imidazopyridines
  作者：Srimanta Manna、Rishikesh Narayan、Christopher Golz、Carsten Strohmann、Andrey P. Antonchick

  DOI：10.1039/c5cc00533g

  日期：——

  We have developed intermolecular annulation of 2-nitrosopyridine derivatives with substituted alkynes for the regioselective access of N-oxide-imidazo[1,2-a]pyridines.

  我们已经开发了2-硝基吡啶衍生物与取代炔烃的分子间环化反应，以实现对N-氧化物-咪唑[1,2-a]吡啶的区域选择性访问。
• Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol
  作者：Baiyuan Yang、Patricia A. Miller、Ute Möllmann、Marvin J. Miller

  DOI：10.1021/ol900997t

  日期：2009.7.2

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.