2-nitromethylene-2,3,4,5,6,7-hexahydro-1H-azepine | 64480-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 2-nitromethylene-2,3,4,5,6,7-hexahydro-1H-azepine
• 英文别名: 2-nitromethylene-azepine；2-Nitromethylen-hexahydroazepin；(2Z)-2-(nitromethylidene)azepane
• CAS: 64480-12-2
• 化学式: C₇H₁₂N₂O₂
• 分子量: 156.184
• InChiKey: VVTVZDUKYJWIDH-SREVYHEPSA-N

物化性质

• 溶解度：
  >23.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

毒理性

• 毒性总结

模拟神经递质的作用，既有兴奋性又有抑制性效果，最终阻断突触后的尼古丁受体。

Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (T10)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

硝基甲烯是有神经毒性的。(T10)

Nitromethylenes are neurotoxic. (T10)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  2-nitromethylene-2,3,4,5,6,7-hexahydro-1H-azepine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以79%的产率得到2-aminomethyl-2,3,4,5,6,7-hexahydro-1H-azepine
  参考文献：
  名称：

  Shukla, U. K.; Khanna, J. M.; Sharma, Satyavan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 7, p. 664 - 668

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙氧基-4,5,6,7-四氢-3H-氮杂卓 、 硝基甲烷 反应 20.0h， 以75%的产率得到2-nitromethylene-2,3,4,5,6,7-hexahydro-1H-azepine
  参考文献：
  名称：

  Shukla, U. K.; Khanna, J. M.; Sharma, Satyavan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 7, p. 664 - 668

  摘要：

  DOI：

文献信息

• [3+3] Cyclization reactions of β-nitroenamines and β-enaminonitriles with α,β-unsaturated carboxylic acid chlorides
  作者：Mihály V. Pilipecz、Tamás R. Varga、Zoltán Mucsi、Pál Scheiber、Péter Nemes

  DOI：10.1016/j.tet.2008.03.090

  日期：2008.6

  New indolizidines, quinolizidines, and octahydro-pyrido[1,2-a]azepines of lactam type were synthesized from 2-nitromethylene-pyrrolidine, -piperidine, and -hexahydroazepine, respectively, by [3+3] cyclizations with α,β-unsaturated carboxylic acid chlorides. In the case of quinolizidines, a double bond migration was observed, and explained in terms of amidity percentage. Cyanomethylene-pyrrolidine gave

  通过[3 + 3]与α，β-的环化反应，分别由2-硝基亚甲基-吡咯烷，-哌啶和-六氢a庚啶合成了内酰胺型的新吲哚并咪唑，喹唑烷和八氢吡啶并[1,2- a ]氮杂ze。不饱和羧酸氯化物。在喹喔啉类的情况下，观察到双键迁移，并且用酰胺百分比来解释。当分别使用简单的开链酰基氯或肉桂酰氯时，氰基亚甲基-吡咯烷产生内酰胺类型的吲哚并咪唑，而1-氰基亚甲基-四氢异喹啉的转化产生内酰胺和酮。
• 1-Amino-2-nitroethene derivatives in triflic acid: NMR study and triflates formation from their hydroxynitrilium ions
  作者：Jean-Marie Coustard

  DOI：10.1016/s0040-4020(99)00244-6

  日期：1999.4

  In triflic acid, 1-amino-2-nitroene derivatives undergo a C,O-diprotonation followed by the loss of (protonated) water, to form the >C=N+< conjugated hydroxynitrilium ions that can react, in a competitive way, either with TfO- or with added C6H6. The resulting phenylated dications can be selectively reduced by NaBH4 at the iminium bond moiety. A protonated nitroso derivative was also isolated as its triflate salt. Structure, reactivity and mechanism of these reactions are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.