2-chlorophenyl α-(2-nitrobenzyl) ketone | 80805-53-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-chlorophenyl α-(2-nitrobenzyl) ketone
• 英文别名: 1-(2-Chlorophenyl)-2-(2-nitrophenyl)ethanone
• CAS: 80805-53-4
• 化学式: C₁₄H₁₀ClNO₃
• mdl: MFCD16350433
• 分子量: 275.691
• InChiKey: NVLDQLKZMZLJQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chlorophenyl α-(2-nitrobenzyl) ketone 在 十二羰基三钌 、 一氧化碳 、 sodium chloride 作用下， 以 乙腈 为溶剂， 220.0 ℃ 、5.0 MPa 条件下， 反应 2.0h， 以94%的产率得到2-(2-chlorophenyl)-1H-indole
  参考文献：
  名称：

  Pizzotti, Maddalena; Cenini, Sergio; Quici, Silvio, Journal of the Chemical Society. Perkin transactions II, 1994, # 4, p. 913 - 918

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(2-chlorophenyl)-3-(dimethylamino)-2-(2-nitrophenyl)prop-2-en-1-one 以37%的产率得到
  参考文献：
  名称：

  MARTIN, L. L.;SETESCAK, L. L.;WORM, M.;CHICHLOW, C. A.;GEYER, H. M. ,, II+, J. MED. CHEM., 1982, 25, N 4, 346-351

  摘要：

  DOI：

文献信息

• Atroposelective Synthesis of Triaryl α‐Pyranones with 1,2‐Diaxes by N‐Heterocyclic Carbene Organocatalysis
  作者：Simiao Zhang、Xiaoxue Wang、Li‐Li Han、Jibin Li、Zheng Liang、Donghui Wei、Ding Du

  DOI：10.1002/anie.202212005

  日期：2022.12.23

  The single-step atroposelective construction of triaryl α-pyranones with stereogenic 1,2-diaxes was accomplished by NHC organocatalysis. The structure of the substrates and the catalytic system play a critical role in the success of this protocol. DFT calculations were performed to rationalize the origin of the high stereoselectivity.

  通过 NHC 有机催化完成了具有立体异构 1,2-二轴的三芳基 α-吡喃酮的单步阻转选择性构建。底物的结构和催化系统对该协议的成功起着至关重要的作用。进行 DFT 计算以合理化高立体选择性的起源。
• (.+-.)-4-Aryl-4,5-dihydro-3H-1,3-benzodiazepines. 2. Nuclear substituted analogs of (.+-.)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and (.+-.)-4,5-dihydro-2-ethyl-3-methyl-4-phenyl-3H-1,3-benzodiazepine as potential antidepressant agents
  作者：Lawrence L. Martin、Linda L. Setescak、Manfred Worm、Charles A. Crichlow、Harry M. Geyer、Jeffrey C. Wilker

  DOI：10.1021/jm00346a004

  日期：1982.4

  Antidepressant-like activity, as evidenced by marked inhibition of tetrabenazine-induced ptosis, was previously reported for (+/-)-4,5-dihydro-4-phenyl-3H-1,3-benzodiazepine derivatives. Since optimal antitetrabenazine activity was associated with (+/-)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine (9k, HRP 543) and the 2-ethyl-3-methyl analogue (10k), the synthesis and evaluation of nuclear-substituted derivatives of these two compounds was also investigated. The initial synthesis involved Friedel-Crafts acylation of substituted benzenes with 2-nitrophenylacetyl chloride to afford 1-aryl-2-(2-nitrophenyl)ethanones 2, which were converted in five steps to (+/-)-alpha-aryl-N-methyl-2-nitrobenzeneethanamines 7. Greater flexibility with respect to the introduction of nuclear substituents was achieved by conversion of 2-nitrotoluene derivatives to 2 via acylation of intermediate beta-(dimethylamino)-2-nitrostyrenes with various aroyl chlorides and hydrolysis. Reductive amination of 2 with methylamine and sodium cyanoborohydride afforded 7 directly and significantly reduced the number of synthetic steps. Reduction of 7a-j to diamines 8a-j and cyclization with appropriate ortho esters gave nuclear-substituted analogues of 9k and 10k. Marked antitetrabenazine activity was associated with many of these compounds. Significant enhancement of activity with respect to the unsubstituted analogues 9k and 10k was not observed, with the exception of 9c which appeared to be slightly more potent than 9k.
• Pizzotti, Maddalena; Cenini, Sergio; Quici, Silvio, Journal of the Chemical Society. Perkin transactions II, 1994, # 4, p. 913 - 918
  作者：Pizzotti, Maddalena、Cenini, Sergio、Quici, Silvio、Tollari, Stefano

  DOI：——

  日期：——
• MARTIN, L. L.;SETESCAK, L. L.;WORM, M.;CHICHLOW, C. A.;GEYER, H. M. ,, II+, J. MED. CHEM., 1982, 25, N 4, 346-351
  作者：MARTIN, L. L.、SETESCAK, L. L.、WORM, M.、CHICHLOW, C. A.、GEYER, H. M. ,, II+

  DOI：——

  日期：——