(R)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanone | 502850-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanone
• CAS: 502850-03-5
• 化学式: C₁₂H₁₄FNO₃
• 分子量: 239.246
• InChiKey: VISNXPGFSDDNSX-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanone 在 氢氧化钾 、 ammonium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 水 为溶剂， 反应 34.0h， 生成 (2SR,3R)-2-(4-fluorophenyl)-3-methylaziridine
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl) propane]dichloroplatinum(II) Complexes

  摘要：

  Enantiomericaily pure 1,2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R,2S)- and (1S,2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by H-1 NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl2 were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl2 even in a concentration of 1 muM. The (1S,2R)- and (1R,2S)-configurated complexes were far less active (SS>RR>RS=SR) and comparable in this respect with the standard cisplatin.

  DOI：

  10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q
• 作为产物：
  描述：

  N-(乙氧羰基)-D-丙氨酸 在 三氯化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (R)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanone
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl) propane]dichloroplatinum(II) Complexes

  摘要：

  Enantiomericaily pure 1,2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R,2S)- and (1S,2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by H-1 NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl2 were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl2 even in a concentration of 1 muM. The (1S,2R)- and (1R,2S)-configurated complexes were far less active (SS>RR>RS=SR) and comparable in this respect with the standard cisplatin.

  DOI：

  10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q