1-(cyclopentylidenemethyl)-2-nitrobenzene | 10299-81-7

• 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: 1-(cyclopentylidenemethyl)-2-nitrobenzene
• 英文别名: (2-nitrobenzylidene)cyclopentane；Cyclopentyliden-<2-nitro-phenyl>-methan
• CAS: 10299-81-7
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: NMJFJTPYIAYSQM-UHFFFAOYSA-N

物化性质

• 沸点：
  342.0±21.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(cyclopentylidenemethyl)-2-nitrobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 tin(ll) chloride 一氧化碳 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以45%的产率得到1,2,3,4-四氢咔唑
  参考文献：
  名称：

  Palladium Complex-Catalyzed Reductive N-Heterocyclization of Nitroarenes: Novel Synthesis of Indole and 2H-Indazole Derivatives

  摘要：

  The dichlorobis(triphenylphosphine)palladium (PdCl2(PPh(3))(2))-tin(II) chloride (SnCl2) system shows high catalytic activity for the reductive N-heterocyclization of various 2-nitrostyrene and N-(2-nitrobenzylidene)amine derivatives when employed at 100 degrees C for 16 h under 20 kg cm(-2) of initial carbon monoxide pressure, to give the corresponding indole and 2H-indazole derivatives in good yield. For example, 2-phenylindole was obtained in 75% yield from the reductive N-heterocyclization of 2-nitrostilbene. Similarly, 2-propyl-2H-indazole was readily prepared in 83% yield by the reductive N-heterocyclization of N-(2-nitrobenzylidene)propylamine. A nitrene intermediate for the present reaction is proposed on the basis of deuterium-labeling experiments and the investigation of alkyl rearrangement in the construction of the indole skeleton. Carbon monoxide effectively operates as a deoxygenating agent of the nitro group to afford a nitrene intermediate.

  DOI：

  10.1021/jo00091a026
• 作为产物：
  描述：

  硝基环戊烷 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 1-(cyclopentylidenemethyl)-2-nitrobenzene
  参考文献：
  名称：

  Access to original spirocyclic derivatives via inter- or intramolecular reaction mediated by manganese(III) acetate

  摘要：

  An easily reproducible protocol allowing inter- or intramolecular spirocyclization on beta-dicarbonyl structures is described. This methodology could afford a wide variety of spirocyclic pharmacophores. As examples, highly substituted spirobenzophenanthridin-6(5H)-ones and spirolactones were synthesized. These scaffolds could be used for the design of many compounds exhibiting biological activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.004

文献信息

• Aryltriolborates as Air- and Water-Stable Bases for Wittig Olefination
  作者：Wenhua Huang、Shuang-Hong Zhao、Ning Xu

  DOI：10.1055/s-0034-1378919

  日期：——

  1-tris(hydroxymethyl)ethane, and aqueous tetrabutylammonium hydroxide. The aryltriolborates can be used as bases in Wittig reactions of aromatic aldehydes with all three types of phosphorus ylides: stabilized and semistabilized ylides can be generated at room temperature, and nonstabilized ylides at 120 °C (bath temperature). Tetrabutylammonium aryltriolborates have been synthesized in 37–66% yield by a one-pot

  摘要 通过一锅法从芳基硼酸，1,1,1-三（羟甲基）乙烷和四丁基氢氧化铵水溶液一锅法合成了芳基三硼酸四丁基铵硼酸酯。三芳基硼酸酯可以用作芳族醛与所有三种类型的磷酰化物的Wittig反应的碱：可以在室温下生成稳定和半稳定的化物，并在120°C（浴温）下生成不稳定的化物。 通过一锅法从芳基硼酸，1,1,1-三（羟甲基）乙烷和四丁基氢氧化铵水溶液一锅法合成了芳基三硼酸四丁基铵硼酸酯。三芳基硼酸酯可以用作芳族醛与所有三种类型的磷酰化物的Wittig反应的碱：可以在室温下生成稳定和半稳定的化物，并在120°C（浴温）下生成不稳定的化物。
• Pyrazole carboxanilide fungicides and use
  申请人：Monsanto Company

  公开号：US05223526A1

  公开（公告）日：1993-06-29

  Novel N-[2-(cyclic alkyl)phenyl]pyrazole-4-carboxamides useful as fungicides, methods of using said compounds, and fungicidal compositions containing them.

  小说N-[2-(环烷基)苯基]吡唑-4-羧酰胺是一种有用的杀真菌剂，使用该化合物的方法以及包含它们的杀真菌组合物。
• Rearrangements and ring expansions during the deoxygenation of .beta.,.beta.-disubstituted o-nitrostyrenes
  作者：Richard J. Sundberg、Toshio Yamazaki

  DOI：10.1021/jo01288a009

  日期：1967.2
• PYRAZOLE CARBOXANILIDE FUNGICIDES
  申请人：MONSANTO COMPANY

  公开号：EP0623113B1

  公开（公告）日：1997-03-05
• US5223526A
  申请人：——

  公开号：US5223526A

  公开（公告）日：1993-06-29