6-(3-nitrophenyl)-1,5-diazabicyclo[3.1.0]hexane | 340295-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3-nitrophenyl)-1,5-diazabicyclo[3.1.0]hexane
• CAS: 340295-21-8
• 化学式: C₁₀H₁₁N₃O₂
• mdl: MFCD02197706
• 分子量: 205.216
• InChiKey: UTMXLMJYPPUYLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  318.1±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3-nitrophenyl)-1,5-diazabicyclo[3.1.0]hexane 以 对二甲苯 为溶剂， 反应 0.58h， 以75%的产率得到1-(3-nitrophenylmethyl)-2-pyrazoline
  参考文献：
  名称：

  摘要：

  Heating of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of N-arylmaleimides gives rise to 2,9-diarylperhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-diones. It is presumed that thermal cleavage of the C-N bond in the diaziridine fragment of the 6-aryl-1,5-diazabicyclo[3.1.0]hexanes results in formation of labile azomethinimines that react with N-arylmaleimides to afford the products of 1,3-dipolar cycloaddition. The rate of accumulation thereof depends only on the character of substituents in the aromatic ring of the 1,5-diazabicyclo[3.1.0]hexanes and is independent of maleimide. The thermal isomerization of 6-aryl-1.5-diazabicyclo[3.1.0]hexanes without 1,3-dipolarophiles yields the corresponding 2-pyrazolines.

  DOI：

  10.1023/a:1012465732305
• 作为产物：
  描述：

  间硝基苯甲醛 、 1,3-丙二胺 在 次氯酸叔丁酯 作用下， 以 甲醇 为溶剂， 生成 6-(3-nitrophenyl)-1,5-diazabicyclo[3.1.0]hexane
  参考文献：
  名称：

  用二氮丙啶原位生成的氮杂氧基烯丙基阳离子的便捷 (3+3) 环化

  摘要：

  使用二氮丙啶，可以在室温下使用碱实现原位形成的氮杂氧基烯丙基阳离子的有效成环，从而提供 1,2,4-三嗪。底物范围、放大、官能团耐受性和无过渡金属反应条件是重要的实用特征。

  DOI：

  10.1039/d3cc02136j

文献信息

• Expedient iron-catalyzed stereospecific synthesis of triazines <i>via</i> cycloaddition of aziridines with diaziridines
  作者：Tanumay Sarkar、Kangkan Talukdar、Subhasish Roy、Tharmalingam Punniyamurthy

  DOI：10.1039/c9cc10089j

  日期：——

  Iron-catalyzed stereospecific [3+3]-annulation of aziridines with diaziridines is described to furnish [1,2,4]-triazines in high yield at room temperature. The use of an inexpensive iron salt catalyst, substrate scope and enantiomeric purity are the important practical features.

  描述了铁催化的氮丙啶与二氮丙啶的立体特异性[3 + 3]-环化反应可在室温下高产率地提供[1,2,4]-三嗪。廉价的铁盐催化剂的使用，底物范围和对映体纯度是重要的实用特征。
• Sc(OTf)₃-Catalyzed Formal [3 + 3] Cycloaddition Reaction of Diaziridines and Quinones for the Synthesis of Benzo[<i>e</i>][1,3,4]oxadiazines
  作者：Jose Cortes Vazquez、Jacqkis Davis、Vladimir N. Nesterov、Hong Wang、Weiwei Luo

  DOI：10.1021/acs.orglett.1c00818

  日期：2021.4.16

  A formal [3 + 3] cyclization reaction of diaziridines and quinones has been developed offering 1,3,4-oxadiazinanes in generally high yields (up to 96%). The reaction was catalyzed by Sc(OTf)3 with a large substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and the dipolar quinones was found to be essential to enable this reaction.

  已开发出正式的重氮丙啶和醌的[3 + 3]环化反应，可提供1,3,4-恶二嗪并通常以高收率（高达96％）提供。该反应由Sc（OTf）3催化，对于二氮丙啶和醌均具有较大的底物范围。发现1，3-偶极二氮丙啶和偶极醌的协同活化对于实现该反应是必不可少的。
• Cobalt-Catalyzed Stereospecific C–N/C–O Bond Formation of Oxiranes with Diaziridines
  作者：Prabhat K. Maharana、Tanumay Sarkar、Subhradeep Kar、Siddhartha K. Purkayastha、Ankur K. Guha、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.joc.3c00445

  日期：2023.7.7

  Co-catalyzed stereospecific C–N and C–O bond formation of oxiranes with diaziridines has been accomplished to furnish tetrahydro-[1,3,4]-oxadiazines at room temperature. Optically active oxiranes can be coupled with high optical purities (>96% ee). Stereoselectivity, functional group tolerance, mechanistic studies using DFT, and natural product modification are the important practical features.

  已经完成了环氧乙烷与二氮丙啶的共催化立体特异性 C-N 和 C-O 键形成，以在室温下提供四氢-[1,3,4]-恶二嗪。光学活性环氧乙烷可以与高光学纯度（> 96% ee）偶联。立体选择性、官能团耐受性、使用 DFT 进行机理研究以及天然产物修饰是重要的实用特征。
• [EN] AGENTS FOR TREATING NEURODEGENERATIVE DISORDERS<br/>[FR] AGENTS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：CRO CONSULTING LTD

  公开号：WO2013121334A3

  公开（公告）日：2013-10-31
• ——
  作者：V. V. Kuznetsov

  DOI：10.1023/a:1023962907733

  日期：——

  A new method was developed for the synthesis of 6-substituted 1,5-diazabicyclo[3.1.0]hexanes and 7-substituted 1,6-diazabicyclo[4.1.0]heptanes by condensation of N-monohalotrimethylene- and N-monohalotetramethylenediamines with carbonyl compounds in the presence of bases. X-ray diffraction studies and quantum-chemical B3LYP/6-31G* calculations demonstrated that the conformations of the resulting bicyclic systems are stabilized by stereoelectronic interactions. As a result, a boat conformation prevails in 1,5-diazabicyclo[3. 1.0]hexanes, whereas the energies of chair, half-chair, and boat conformations of 1,6-diazabicyclo[4.1.0]heptanes are equalized.