N-(2,6-dimethylphenyl)-3-oxo-3-phenyl-propionamide | 40624-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,6-dimethylphenyl)-3-oxo-3-phenyl-propionamide
• 英文别名: N-(2,6-dimethylphenyl)-3-oxo-3-phenylpropanamide
• CAS: 40624-74-6
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: SAGKWXPLWULWTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,6-dimethylphenyl)-3-oxo-3-phenyl-propionamide 在 一水合肼 作用下， 以 吡啶 为溶剂， 反应 4.0h， 以68%的产率得到(2,6-dimethylphenyl)-(5-phenyl-1H-pyrazol-3-yl)-amine
  参考文献：
  名称：

  某些新型杂环木糖胺和羧酰胺的合成

  摘要：

  将二甲苯胺1a，1b与氰基乙酸乙酯2和乙酸乙酯基苯甲酰15缩合，分别得到氰基乙酰苯胺3a，3b和β-二酮16a，16b。化合物3a，3b与肼和苯肼反应可得到嗪双衍生物5a，5b和7a，7b，而16a，16b与相同的试剂反应可得到吡唑基胺衍生物17a，17b和18a，18b分别。化合物3a，3b也与二甲基甲酰胺二甲基乙缩醛反应，得到烯胺腈8a，8b，而16a，16b与相同的试剂反应，仅得到烯胺酮19b。烯腈8a，8b与肼和苯基肼反应，分别分别得到嗪双衍生物11a，11b和14a，14b。

  DOI：

  10.1002/jhet.1996
• 作为产物：
  描述：

  苯基丙醇水合物 在 氯化铵 、 锌 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 72.5h， 生成 N-(2,6-dimethylphenyl)-3-oxo-3-phenyl-propionamide
  参考文献：
  名称：

  A new synthesis of β-keto amides by reduction of Passerini adducts

  摘要：

  The Passerini reaction between glyoxals, isocyanides and acetic acid forms beta-keto acyloxyamides, which are readily transformed in beta-keto amides by reductive deacetoxylation with zinc. The versatility of this procedure, which allows introducing different groups both in position-3 and the amide nitrogen, makes it ideal for its use in diversity-oriented synthesis. in combination with subsequent complexity generation reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.041

文献信息

• Azomethine Dyes. II. Color and Constitution of Acylacetamide Azomethine Dyes
  作者：G. H. Brown、J. Figueras、R. J. Gledhill、C. J. Kibler、F. C. McCrossen、S. M. Parmerter、P. W. Vittum、A. Weissberger

  DOI：10.1021/ja01568a062

  日期：1957.6
• New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides
  作者：Kamelia M. Amin、Magda M.F. Ismail、Eman Noaman、Dalia H. Soliman、Yousry A. Ammar

  DOI：10.1016/j.bmc.2006.06.038

  日期：2006.10

  Hypoxic cells which are common feature of solid tumors are resistant to both anticancer drugs and radiation therapy. Thus, the identification of drugs with the selective toxicity toward hypoxic cells is an important target in anticancer chemotherapy. Tirapazamine has been shown to be an efficient and selective cytotoxin after bioreductive activation in hypoxic cells which is thought to be due to the presence of the 1,4-di-N-oxide. A new series of quinoxaline 1,4-di-N-oxides and fused quinoxaline di-N-oxides were synthesized and evaluated for hypoxic-cytotoxic activity on EAC cell line. Compound 10a was the most potent cytotoxin IC50 0.9 mu g/mL, potency 75 mu g/mL, and was approximately 15 times more selective cytotoxin (HCR > 111) than 3-aminoquinoxaline-2-carbonitrile which has been used as a standard (HCR > 7.5). Compounds 4 and 3a,b were more selective than the standard. In addition, antitumor activity against Hepg2 (liver) and U251 (brain) human cell lines was evaluated, compounds 9c and 8a were the most active against Hepg2 with IC50 values 1.9 and 2.9 mu g/mL, respectively, however, all the tested compounds were nontoxic against U251 cell line. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Some Novel Heterocyclic Xylidinyl Amines and Carboxamides
  作者：Fathy M. Abdelrazek、Mohamed S. Farghaly、Hussein E. Abdelrahman

  DOI：10.1002/jhet.1996

  日期：2015.1

  respectively. Compounds 3a, 3b react with hydrazine and phenyl hydrazine to afford the azine‐bis derivatives 5a, 5b and 7a, 7b, whereas 16a, 16b react with the same reagents to afford the pyrazolyl amine derivatives 17a, 17b and 18a, 18b, respectively. Compounds 3a, 3b react also with dimethylformamide dimethylacetal to afford the enaminonitriles 8a, 8b, whereas 16a, 16b react with the same reagent

  将二甲苯胺1a，1b与氰基乙酸乙酯2和乙酸乙酯基苯甲酰15缩合，分别得到氰基乙酰苯胺3a，3b和β-二酮16a，16b。化合物3a，3b与肼和苯肼反应可得到嗪双衍生物5a，5b和7a，7b，而16a，16b与相同的试剂反应可得到吡唑基胺衍生物17a，17b和18a，18b分别。化合物3a，3b也与二甲基甲酰胺二甲基乙缩醛反应，得到烯胺腈8a，8b，而16a，16b与相同的试剂反应，仅得到烯胺酮19b。烯腈8a，8b与肼和苯基肼反应，分别分别得到嗪双衍生物11a，11b和14a，14b。
• A new synthesis of β-keto amides by reduction of Passerini adducts
  作者：Ana G. Neo、Jose Delgado、Cecilia Polo、Stefano Marcaccini、Carlos F. Marcos

  DOI：10.1016/j.tetlet.2004.11.041

  日期：2005.1

  The Passerini reaction between glyoxals, isocyanides and acetic acid forms beta-keto acyloxyamides, which are readily transformed in beta-keto amides by reductive deacetoxylation with zinc. The versatility of this procedure, which allows introducing different groups both in position-3 and the amide nitrogen, makes it ideal for its use in diversity-oriented synthesis. in combination with subsequent complexity generation reactions. (C) 2004 Elsevier Ltd. All rights reserved.