1-(3,4-dimethoxyphenyl)-2-(2-nitrophenyl)ethan-1-one | 56766-91-7

• 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-(3,4-dimethoxyphenyl)-2-(2-nitrophenyl)ethan-1-one
• 英文别名: 1-(3,4-Dimethoxy-phenyl)-2-(2-nitro-phenyl)-ethanone；1-(3,4-Dimethoxyphenyl)-2-(2-nitrophenyl)ethanone
• CAS: 56766-91-7
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: NQQXTXPCTOBKOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-2-(2-nitrophenyl)ethan-1-one 在 palladium on activated charcoal 氢氧化钾 、 硼烷四氢呋喃络合物 、 盐酸羟胺 、 氢气 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 25.0~60.0 ℃ 、344.73 kPa 条件下， 反应 2.5h， 生成 4,5-dihydro-4-(3,4-dimethoxyphenyl)-2,3-dimethyl-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：

  邻苯二甲醚 、 2-硝基苯乙酸 在 氯化亚砜 、 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以45 %的产率得到1-(3,4-dimethoxyphenyl)-2-(2-nitrophenyl)ethan-1-one
  参考文献：
  名称：

  TiCl3介导的2-(邻-硝基芳基)-取代烯醇酯还原环化合成3-酰氧基二氢吲哚

  摘要：

  在TiCl 3存在下，带有2-(邻-硝基芳基)取代基的四取代烯醇酯的还原环化以良好的收率得到3-酰氧基-2,3-二取代的二氢吲哚。多米诺骨牌过程涉及将硝基部分还原为亚硝基，然后进行 5-中心-6π-电环化、1,2-酰氧基迁移以及所得硝酮中间体的进一步还原，这是反应结果的原因。如此获得的二氢吲哚通过一系列皂化和半频哪醇重排顺利转化为 2,2-二取代羟吲哚。

  DOI：

  10.1021/acs.orglett.2c02860

文献信息

• MARTIN, LAWRENCE L.;WORM, MANFRED;CRICHLOW, CHARLES A.
  作者：MARTIN, LAWRENCE L.、WORM, MANFRED、CRICHLOW, CHARLES A.

  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：——
• MAYER, K. K.;PRIOR, S.;WIEGREBE, W., MONATSH. CHEM., 1986, 117, N 4, 511-532
  作者：MAYER, K. K.、PRIOR, S.、WIEGREBE, W.

  DOI：——

  日期：——
• DYKE S. F.; TILEY E. P.; WHITE A. W. C.; GALE D. P., TETRAHEDRON <TETR-AB>, 1975, 31, NO 9, 1219-1222
  作者：DYKE S. F.、 TILEY E. P.、 WHITE A. W. C.、 GALE D. P.

  DOI：——

  日期：——
• METHOD AND KIT FOR MEASURING ENZYMATIC ACTIVITIES OF VARIOUS CYTOCHROME P450 MOLECULE SPECIES COMPREHENSIVELY AND WITH HIGH EFFICIENCY
  申请人：Imaishi Hiromasa

  公开号：US20120288885A1

  公开（公告）日：2012-11-15

  The present invention relates to a method, and a kit, for measuring the enzymatic activity of cytochrome P450 comprehensively and with high efficiency and accuracy, wherein an oxygen sensing layer and a cytochrome P450-supporting layer are vertically integrated on a chip, and cytochrome P450 is supported in a hydrophilic polymer matrix in the cytochrome P450-supporting layer, the cytochrome P450 generates NADPH by being irradiated with light in the presence of at least one caged compound selected from the group consisting of caged-NADP and caged-G6P, an enzyme utilizing NADPH as a coenzyme (i.e., cytochrome P450 reductase) and a substrate thereof to supply NADP and/or G6P from the caged compound to generate NADPH to start the reaction between the enzyme and a substrate.