Pyrrolo(2,1-a)isoquinoline, 1,2,3,5,6,10b-hexahydro-6-(4-(methyl-11c-thio)phenyl)-, (6R,10bS)- | 151121-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: Pyrrolo(2,1-a)isoquinoline, 1,2,3,5,6,10b-hexahydro-6-(4-(methyl-11c-thio)phenyl)-, (6R,10bS)-
• 英文别名: (6R,10bS)-6-(4-(111C)methylsulfanylphenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
• CAS: 151121-38-9
• 化学式: C₁₉H₂₁NS
• 分子量: 294.437
• InChiKey: YVKDUIAAPBKHMJ-POJGKFHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [11C]methyl iodide 、 (6R,10bS)-4-(1,2,3,5,6,10b-Hexahydro-pyrrolo[2,1-a]isoquinolin-6-yl)-benzenethiol 反应 0.03h， 生成 Pyrrolo(2,1-a)isoquinoline, 1,2,3,5,6,10b-hexahydro-6-(4-(methyl-11c-thio)phenyl)-, (6R,10bS)-
  参考文献：
  名称：

  Efficient synthesis of enantiomerically pure thioester precursors of [11C]McN-5652 from racemic McN-5652

  摘要：

  An improved synthesis of the enantiomerically pure thioester precursors of [C-11](+)-McN-5652 ([C-11](+)-1), and [C-11](-)-McN5652 ([C-11](-)-1) starting from racemic McN-5652 ((+/-)-1) is described. The Synthetic method includes the resolution of (+/-)-1 by:repeated crystallization of the (+)- and (-)-di-p-toluoyltartrates yielding (+)-McN-5652 ((+)-1) and (-)-McN-5652 ((-)-1), each with >98% enantiomeric purity. S-Demethylation of (+/-)-1, (+)-1 and (-)-1, respectively was achieved by:treatment with sodium amide at low temperatures (-78 degrees C) followed by conversion of the intermediate thiols 2 with acetyl chloride to give the corresponding thioester precursors (+/-)-3, (+)-3 oy:(-)-3. This demethylation method almost completely suppressed the isomerization of the pharmacologically active trans diastereomer into the inactive cis form. Chiral HPLC analyses confirmed that the S-demethylation proceeded without any racemization. C-11-labelling of(+)-3 or (-)-3 yields :enantiomerically pure [C-11](+)-McN-5652 or [C-11](-)-McN5652, each in 22 % radiochemical yield (decay-corrected, related to [C-11]CO2) and a specific radioactivity of 74 GBq/mu mol (2 Ci/mu mol) at the end of synthesis (EOS).

  DOI：

  10.1002/(sici)1099-1344(19991230)42:13<1301::aid-jlcr298>3.0.co;2-2

文献信息

• Efficient synthesis of enantiomerically pure thioester precursors of [11C]McN-5652 from racemic McN-5652
  作者：J. Zessin、P. Gucker、S. M. Ametamey、J. Steinbach、P. Brust、F. X. Vollenweider、B. Johannsen、P. A. Schubiger

  DOI：10.1002/(sici)1099-1344(19991230)42:13<1301::aid-jlcr298>3.0.co;2-2

  日期：1999.12.30

  An improved synthesis of the enantiomerically pure thioester precursors of [C-11](+)-McN-5652 ([C-11](+)-1), and [C-11](-)-McN5652 ([C-11](-)-1) starting from racemic McN-5652 ((+/-)-1) is described. The Synthetic method includes the resolution of (+/-)-1 by:repeated crystallization of the (+)- and (-)-di-p-toluoyltartrates yielding (+)-McN-5652 ((+)-1) and (-)-McN-5652 ((-)-1), each with >98% enantiomeric purity. S-Demethylation of (+/-)-1, (+)-1 and (-)-1, respectively was achieved by:treatment with sodium amide at low temperatures (-78 degrees C) followed by conversion of the intermediate thiols 2 with acetyl chloride to give the corresponding thioester precursors (+/-)-3, (+)-3 oy:(-)-3. This demethylation method almost completely suppressed the isomerization of the pharmacologically active trans diastereomer into the inactive cis form. Chiral HPLC analyses confirmed that the S-demethylation proceeded without any racemization. C-11-labelling of(+)-3 or (-)-3 yields :enantiomerically pure [C-11](+)-McN-5652 or [C-11](-)-McN5652, each in 22 % radiochemical yield (decay-corrected, related to [C-11]CO2) and a specific radioactivity of 74 GBq/mu mol (2 Ci/mu mol) at the end of synthesis (EOS).