1-(2-Fluoro-phenyl)-2-(2-nitro-phenyl)-ethanone oxime | 75842-61-4

• 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: 1-(2-Fluoro-phenyl)-2-(2-nitro-phenyl)-ethanone oxime
• 英文别名: 1-(2-Fluorophenyl)-2-(2-nitrophenyl)ethanone oxime；N-[1-(2-fluorophenyl)-2-(2-nitrophenyl)ethylidene]hydroxylamine
• CAS: 75842-61-4
• 化学式: C₁₄H₁₁FN₂O₃
• 分子量: 274.251
• InChiKey: TXPUUABAGBDRRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 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：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-Fluoro-phenyl)-2-(2-nitro-phenyl)-ethanone oxime 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 硼烷四氢呋喃络合物 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 2.0h， 生成 4,5-dihydro-2,3-dimethyl-4-(2-fluorophenyl)-3H-1,3-benzodiazepine
  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：

  邻氟苯甲酰氯 在 盐酸羟胺 、 水 、 sodium acetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 1-(2-Fluoro-phenyl)-2-(2-nitro-phenyl)-ethanone oxime
  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

文献信息

• Process for preparing 4-phenyl-1,3-benzodiazepines
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04409145A1

  公开（公告）日：1983-10-11

  Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.

  本发明涉及一种新型的4-苯基-1,3-苯二氮卓类化合物、其新型中间体及其制备方法。这些苯二氮卓类化合物可用作抗抑郁剂、镇痛剂和抗癫痫剂。
• Carboxamides of 2-amino-alpha-phenlphenethylamines
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05185465A1

  公开（公告）日：1993-02-09

  Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.

  本发明涉及新的4-苯基-1,3-苯二氮平衍生物和2-氨基-α-苯基苯乙胺衍生物中间体及其制备方法。这些苯二氮平衍生物可用作抗抑郁剂、镇痛剂和抗癫痫剂。2-氨基-α-苯基苯乙胺可用作抗癫痫和神经保护剂。
• Dianthus plant named ‘KLEDG19303’
  申请人：Klemm+Sohn GmbH & Co. KG

  公开号：USPP032444P2

  公开（公告）日：2020-11-10

  A new Dianthus plant named ‘KLEDG19303’ particularly distinguished by single flowers with a magenta flower color with a purple center, a maculated flower pattern and green-grey leaf color, is disclosed.

  一种新的石竹植物，名为“KLEDG19303”，其特点是单朵花具有洋红色的花色和紫色的中心，有斑点花纹和绿灰色的叶色。
• Intermediates for the preparation of 4-phenyl-1,3-benzodiazepines
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04933493A1

  公开（公告）日：1990-06-12

  Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.

  本发明涉及新型4-苯基-1,3-苯二氮卓类化合物、其新型中间体以及制备方法。这些苯二氮卓类化合物可用作抗抑郁剂、镇痛剂和抗癫痫剂。
• 2-amino-alpha-phenylphenethylamines and method of use
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04968721A1

  公开（公告）日：1990-11-06

  Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.

  本发明描述了新颖的4-苯基-1,3-苯二氮平和2-氨基-α-苯基苯乙胺，以及它们的新颖中间体和制备方法。这些苯二氮平可用作抗抑郁剂、镇痛剂和抗惊厥剂。2-氨基-α-苯基苯乙胺可用作抗惊厥和神经保护剂。