(R)-9-<<3-(tert-butylamino)-2-hydroxypropyl>oximino>fluorene | 81522-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-9-<<3-(tert-butylamino)-2-hydroxypropyl>oximino>fluorene
• 英文别名: (2R)-1-(tert-butylamino)-3-(fluoren-9-ylideneamino)oxypropan-2-ol
• CAS: 81522-06-7
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: DSKDPDQUXBBVRD-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  53.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-芴酮肟 在 sodium hydride 作用下， 反应 17.0h， 生成 (R)-9-<<3-(tert-butylamino)-2-hydroxypropyl>oximino>fluorene
  参考文献：
  名称：

  Use of (S)-(trifloxymethyl)oxirane in the synthesis of a chiral .beta.-adrenoceptor antagonist, (R)- and (S)-9-[[3-(tert-butylamino)-2-hydroxypropyl]oximino]fluorene

  摘要：

  Two synthetic approaches were used to prepare, in chirally pure form, the beta-adrenoceptor antagonist 9-[[3-(tert-butylamino)-2-hydroxypropyl]oximino]fluorene (1a). One of these employed the oxazolidine (S)-6 generated from D-mannitol, while the other utilized (S)-[[(trifluoromethanesulfonyl)oxy]methyl]oxirane (4) as the chiral three-carbon fragment. This latter synthesis was designed to incorporate the amino function in the last step. In vitro, a beta 2 selectivity of only 2.2 was observed for 1a. The example, (S)-9-[[3-(tert-amylamino)-2-hydroxypropyl]oximino]fluorene (1b), was also prepared and found to be selective for the beta 1 receptor by a factor of 2.5. In contrast to other beta-adrenoceptor antagonists, the enantiomers of 1a exhibited no chiral preference; i.e., (S)-1a and (R)-1a possessed a similar order of beta-adrenoceptor antagonistic activity.

  DOI：

  10.1021/jm00350a009

文献信息

• LECLERC, G.;AMLAIKY, N.;ROUOT, B., EUR. J. MED. CHEM.-CHIM. THER., 1982, 17, N 1, 69-74
  作者：LECLERC, G.、AMLAIKY, N.、ROUOT, B.

  DOI：——

  日期：——
• BALDWIN, J. J.;MCCLURE, D. E.;GROSS, D. M.;WILLIAMS, M., J. MED. CHEM., 1982, 25, N 3, 931-936
  作者：BALDWIN, J. J.、MCCLURE, D. E.、GROSS, D. M.、WILLIAMS, M.

  DOI：——

  日期：——
• Use of (S)-(trifloxymethyl)oxirane in the synthesis of a chiral .beta.-adrenoceptor antagonist, (R)- and (S)-9-[[3-(tert-butylamino)-2-hydroxypropyl]oximino]fluorene
  作者：John J. Baldwin、David E. McClure、Dennis M. Gross、Michael Williams

  DOI：10.1021/jm00350a009

  日期：1982.8

  Two synthetic approaches were used to prepare, in chirally pure form, the beta-adrenoceptor antagonist 9-[[3-(tert-butylamino)-2-hydroxypropyl]oximino]fluorene (1a). One of these employed the oxazolidine (S)-6 generated from D-mannitol, while the other utilized (S)-[[(trifluoromethanesulfonyl)oxy]methyl]oxirane (4) as the chiral three-carbon fragment. This latter synthesis was designed to incorporate the amino function in the last step. In vitro, a beta 2 selectivity of only 2.2 was observed for 1a. The example, (S)-9-[[3-(tert-amylamino)-2-hydroxypropyl]oximino]fluorene (1b), was also prepared and found to be selective for the beta 1 receptor by a factor of 2.5. In contrast to other beta-adrenoceptor antagonists, the enantiomers of 1a exhibited no chiral preference; i.e., (S)-1a and (R)-1a possessed a similar order of beta-adrenoceptor antagonistic activity.