2-(硝基甲基)-1,3-苯并恶唑 | 24998-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 2-(硝基甲基)-1,3-苯并恶唑
• 英文名称: 2-Nitromethylbenzoxazol
• 英文别名: Benzoxazole, 2-(nitromethyl)-；2-(nitromethyl)-1,3-benzoxazole
• CAS: 24998-80-9
• 化学式: C₈H₆N₂O₃
• 分子量: 178.147
• InChiKey: BZDWOFCRSSJURY-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  298.2±23.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(硝基甲基)-1,3-苯并恶唑 在 platinum(IV) oxide 氢气 、 三溴化磷 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.0h， 生成 4-(2-benzoxazolyl)-4-(benzylideneamino)butanentrile
  参考文献：
  名称：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation

  摘要：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.

  DOI：

  10.1021/jm00117a010
• 作为产物：
  描述：

  2-甲基苯并唑 在 lithium diisopropyl amide 、 硝酸甲酯 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 以18%的产率得到2-(硝基甲基)-1,3-苯并恶唑
  参考文献：
  名称：

  Fluorination and chlorination of nitroalkyl groups

  摘要：

  Heterocycles substituted with a nitromethyl (CH2NO2) or phenyl-nitromethyl (CHPhNO2) group were prepared by reaction of a methyl- or phenylmethyl-substituted heterocycle, respectively, with lithium di-isopropylamide followed by quenching the intermediate carbanion with methyl nitrate. Conversion of CH2NO2 attached to an alkyl or aryl moiety into a dichloronitromethyl (CCl2NO2) group was achieved using N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) in dichloromethane. Similarly, CH2NO2 attached to an alkyl or aryl group was converted into difluoronitromethyl (CF2NO2) using either 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis( tetrafluoroborate) (Selectfluor (TM)) or N-fluorobenzenesulfonimide with DBU as base and dichloromethane as solvent. Reaction of omega-nitroacetophenone with Selectfluor/DBU in dimethylformamide followed by acidification and distillation gave the parent difluoronitromethane in a useful 'one-pot' procedure. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.020

文献信息

• Alkyl nitrate nitration of active methylene compounds. IX. Nitration of alkyl substituted heterocyclic compounds
  作者：H. Feuer、J. P. Lawrence

  DOI：10.1021/jo00796a021

  日期：1972.11
• Buevich,V.A. et al., Journal of Organic Chemistry USSR (English Translation), 1978, vol. 14, p. 2031 - 2035
  作者：Buevich,V.A. et al.

  DOI：——

  日期：——
• Schaefer,H.; Gewald,K., Zeitschrift fur Chemie, 1976, vol. 16, # 7, p. 272
  作者：Schaefer,H.、Gewald,K.

  DOI：——

  日期：——
• Microwave-Assisted Synthesis of<i>N</i>-Heterocycles and Their Evaluation Using an Acetylcholinesterase Immobilized Capillary Reactor
  作者：Diego P. Sangi、Julia L. Monteiro、Kenia L. Vanzolini、Quezia B. Cass、Marcio W. Paixão、Arlene G. Corrêa

  DOI：10.5935/0103-5053.20140056

  日期：——

  Os etenoditioacetais polarizados sao conhecidos como importantes intermediarios em muitos processos de sintese. Neste trabalho, reporta-se a anelacao livre de metal de transicao de 1,1-bis(tiometil)-2-nitroetileno com hidroxilalquilaminas e alquildiaminas. Esta metodologia permite a sintese direta de N-heterociclos tais como imidazolidinas, oxazolidinas e benzoxazis sob irradiaao de micro-ondas. Estes compostos foram avaliados como inibidores da acetilcolinesterase usando um reator capilar contendo a enzima imobilizada acoplado a um espectrmetro de massas.Polarized ketene dithioketals have been recognized as useful building blocks in many synthetic operations. In this work, a transition-metal-free annulations of 1,1-bis(thiomethyl)-2-nitroethylene with hydroxylalkylamines or alkyldiamines have been reported. This methodology provides a directed approach to N-heterocycles, e.g., imidazolidines, oxazolidines and benzoxazoles under microwave conditions. These compounds were evaluated as acetylcholinesterase inhibitors by using an enzyme immobilized capillary reactor-tandem mass spectrometry.
• CHUJGUK V. A.; FEDOTOV K. V., UKR. XIM. ZH., 1980, 46, HO 12, 1306-1310
  作者：CHUJGUK V. A.、 FEDOTOV K. V.

  DOI：——

  日期：——