1-phenyl-2-(5-chloro-2-nitrophenyl)ethan-1-one | 80805-54-5

• 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: 1-phenyl-2-(5-chloro-2-nitrophenyl)ethan-1-one
• 英文别名: 2-(5-chloro-2-nitro)phenyl-1-phenylethanone；2-(5-chloro-2-nitrophenyl)-1-phenylethanone
• CAS: 80805-54-5
• 化学式: C₁₄H₁₀ClNO₃
• 分子量: 275.691
• InChiKey: IGKJXFPSBPAOMX-UHFFFAOYSA-N

物化性质

• 熔点：
  111-116 °C(Solv: ethanol (64-17-5))
• 沸点：
  413.9±30.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

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：
  0.07
• 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：

  1-phenyl-2-(5-chloro-2-nitrophenyl)ethan-1-one 在 硼烷四氢呋喃络合物 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-(5-Chloro-2-nitrophenyl)-1-phenylethanamine
  参考文献：
  名称：

  (.+-.)-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

  摘要：

  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.

  DOI：

  10.1021/jm00346a004
• 作为产物：
  描述：

  (E)-2-(5-chloro-2-nitrophenyl)-3-(dimethylamino)-1-phenylprop-2-en-1-one 以16%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

• Nucleophilic addition of silyl enol ethers to aromatic nitro compounds: scope and mechanism of reaction
  作者：T. V. RajanBabu、G. S. Reddy、Tadamichi Fukunaga

  DOI：10.1021/ja00305a024

  日期：1985.9

  chloride are not displaced in the reaction, suggesting the absence of radical ion intermediates. Dihydroaromatic nitro derivatives can be isolated in some cases, such as anthracene and naphthalene systems which are less prone to rearomatize. The use of silicon reagents in organic synthesis has been ex- panding rapidly in the past few year^,^-^ and versatile methods for carbon-carbon bond formations have been

  与碱金属烯醇化物形成鲜明对比的是，在氟离子源的存在下，甲硅烷基烯醇醚和烯酮甲硅烷基缩醛加成到芳香硝基化合物中，得到中间体二氢芳香硝基化合物，这可以通过 NMR 观察到。中间体与硼胺或 DDQ 的原位氧化以中等至高产率产生α-硝基芳基羰基化合物。该反应适用于烷基、烷氧基和卤素取代的硝基苯以及杂环和稠合硝基芳族化合物。虽然硝基的邻位取代主要用空间上要求不高的甲硅烷基试剂，但对位取代产物仅用体积大的试剂获得。然而，通过用适当的基团（例如氯）封闭对位，可以将加成指向邻位。卤代硝基芳烃和对硝基枯烯基氯的卤素原子在反应中没有被置换，表明不存在自由基离子中间体。在某些情况下可以分离二氢芳族硝基衍生物，例如不太容易重构化的蒽和萘系统。在过去的几年里，硅试剂在有机合成中的应用迅速扩大，基于由氟离子源活化的甲硅烷基烯醇醚，已经开发出用于碳-碳键形成的通用方法。各种研究小组已经报道了烷基化^、^^^^ 芳基化~ns、~aldol
• Facile Synthesis of 3-Substituted 2,1-Benzisoazoles (Anthranils)
  作者：Zbigniew Wróbel

  DOI：10.1055/s-1997-1413

  日期：1997.7

  A simple and efficient method of Me3SiCl/Et3N mediated dehydration of 2-nitrobenzyl derivatives to 3-substituted anthranils is reported.

  报告了一种由 Me3SiCl/Et3N 介导的 2-硝基苄基衍生物脱水成 3-取代蒽的简单而高效的方法。
• 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。
• Wrobel, Z.; Makosza, M., Polish Journal of Chemistry, 1992, vol. 66, # 12, p. 2005 - 2008
  作者：Wrobel, Z.、Makosza, M.

  DOI：——

  日期：——
• Iwasaki, Genji; Hamana, Masatomo; Saeki, Seitaro, Heterocycles, 1982, vol. 19, # 1, p. 162
  作者：Iwasaki, Genji、Hamana, Masatomo、Saeki, Seitaro

  DOI：——

  日期：——