(3S)-3-ethyl-5-(4-fluorophenyl)-1,3-dimethylindol-2-one | 1318251-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S)-3-ethyl-5-(4-fluorophenyl)-1,3-dimethylindol-2-one
• CAS: 1318251-49-8
• 化学式: C₁₈H₁₈FNO
• 分子量: 283.345
• InChiKey: MFMOAAZTHIRMQP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3R,5'S)-1-methyl-5'-((R)-1-phenylethoxy)-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophen]-2-one 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 氢气 、 三正丁基氢锡 、 碳酸氢钠 、 三氟乙酸 、 sodium iodide 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (3S)-3-ethyl-5-(4-fluorophenyl)-1,3-dimethylindol-2-one
  参考文献：
  名称：

  A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles as progesterone receptor antagonists

  摘要：

  A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles is reported. Compound (2) prepared by radical cyclisation of (1) was used for the synthesis of racemic and enantiomerically pure 3-asymmetrically substituted oxindoles. Desulfurisation of (2) using Raney Ni yielded the racemate (5). Addition of (S)-1-phenylethanol to compound (2) yielded the diastereoisomer (21) the structure of which was determined using X-ray crystallography. Using a sequence of steps (21) was converted to the enantiomer (8). The enantiomer (9) was similarly prepared from (2) using (R)-1-phenylethanol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.120

文献信息

• A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles as progesterone receptor antagonists
  作者：S. Alluri、H. Feng、M. Livings、L. Samp、D. Biswas、T.W. Lam、E. Lobkovsky、A.K. Ganguly

  DOI：10.1016/j.tetlet.2011.05.120

  日期：2011.7

  A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles is reported. Compound (2) prepared by radical cyclisation of (1) was used for the synthesis of racemic and enantiomerically pure 3-asymmetrically substituted oxindoles. Desulfurisation of (2) using Raney Ni yielded the racemate (5). Addition of (S)-1-phenylethanol to compound (2) yielded the diastereoisomer (21) the structure of which was determined using X-ray crystallography. Using a sequence of steps (21) was converted to the enantiomer (8). The enantiomer (9) was similarly prepared from (2) using (R)-1-phenylethanol. (C) 2011 Elsevier Ltd. All rights reserved.