(+)-(1R,2S)-methyl 2-[-(3R)-(3,4-dihydro-3-methyl-β-carbolin-1-yl)methyl]cyclohexane-1-carboxylate | 451498-64-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (+)-(1R,2S)-methyl 2-[-(3R)-(3,4-dihydro-3-methyl-β-carbolin-1-yl)methyl]cyclohexane-1-carboxylate
• CAS: 451498-64-9
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: RALHSQZADUUDIZ-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  54.45
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2S)-methyl 2-[-(3R)-(3,4-dihydro-3-methyl-β-carbolin-1-yl)methyl]cyclohexane-1-carboxylate 在 咪唑 、 lithium aluminium tetrahydride 、 碘 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (+)-(3R,5R,15S,20R)-5-methylyohimbane
  参考文献：
  名称：

  5-甲基育亨班八种非对映异构体的合成及构象分析

  摘要：

  Some time ago, Siddiqui et al. proposed structure 1 for the naturally occurring indole alkaloid yohambinine, which they had isolated from Rauwolfia serpentine BENTH. In the present paper, enantioselective syntheses of all eight diastereoisomers endowed with the proposed 5-methylyohimbane structure are disclosed. However, none of the synthetically prepared compounds showed spectroscopic properties identical with those reported for the natural product yohambinine, which, therefore, must possess an altogether different constitutional formula. The ground-state conformations of the diastereoisomers 1, 14, 18, 19, 21, 22, 25, and 26 were deduced by spectroscopic methods, and the outcome was compared with the results of extensive force-field, semi-empirical, and ab-initio calculations.

  DOI：

  10.1002/1522-2675(200203)85:3<945::aid-hlca945>3.0.co;2-a
• 作为产物：
  描述：

  (R)-alpha-甲基色胺 在 三正丁胺 、 2-氯-1-甲基吡啶碘化物 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (+)-(1R,2S)-methyl 2-[-(3R)-(3,4-dihydro-3-methyl-β-carbolin-1-yl)methyl]cyclohexane-1-carboxylate
  参考文献：
  名称：

  5-甲基育亨班八种非对映异构体的合成及构象分析

  摘要：

  Some time ago, Siddiqui et al. proposed structure 1 for the naturally occurring indole alkaloid yohambinine, which they had isolated from Rauwolfia serpentine BENTH. In the present paper, enantioselective syntheses of all eight diastereoisomers endowed with the proposed 5-methylyohimbane structure are disclosed. However, none of the synthetically prepared compounds showed spectroscopic properties identical with those reported for the natural product yohambinine, which, therefore, must possess an altogether different constitutional formula. The ground-state conformations of the diastereoisomers 1, 14, 18, 19, 21, 22, 25, and 26 were deduced by spectroscopic methods, and the outcome was compared with the results of extensive force-field, semi-empirical, and ab-initio calculations.

  DOI：

  10.1002/1522-2675(200203)85:3<945::aid-hlca945>3.0.co;2-a

文献信息

• Synthesis and Conformational Analysis of All Eight Diastereoisomers of 5-Methylyohimbane
  作者：Christian Lohse、Richard Detterbeck、Pierre Acklin、Hans-Jürg Borschberg

  DOI：10.1002/1522-2675(200203)85:3<945::aid-hlca945>3.0.co;2-a

  日期：2002.3

  Some time ago, Siddiqui et al. proposed structure 1 for the naturally occurring indole alkaloid yohambinine, which they had isolated from Rauwolfia serpentine BENTH. In the present paper, enantioselective syntheses of all eight diastereoisomers endowed with the proposed 5-methylyohimbane structure are disclosed. However, none of the synthetically prepared compounds showed spectroscopic properties identical with those reported for the natural product yohambinine, which, therefore, must possess an altogether different constitutional formula. The ground-state conformations of the diastereoisomers 1, 14, 18, 19, 21, 22, 25, and 26 were deduced by spectroscopic methods, and the outcome was compared with the results of extensive force-field, semi-empirical, and ab-initio calculations.