(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-3,3,12a-trideuterio-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione | 1021702-43-1

• 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: (6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-3,3,12a-trideuterio-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
• CAS: 1021702-43-1
• 化学式: C₂₂H₁₉N₃O₄
• 分子量: 392.387
• InChiKey: WOXKDUGGOYFFRN-YHKMLGTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  他达那非 在 重水 、 potassium carbonate 作用下， 以 四氢呋喃 、 氘代二甲亚砜 为溶剂， 反应 16.0h， 以94%的产率得到(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-3,3,12a-trideuterio-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  Highly stereoselective Pictet–Spengler reaction of d-tryptophan methyl ester with piperonal: convenient syntheses of Cialis (Tadalafil), 12a-epi-Cialis, and their deuterated analogues

  摘要：

  The acid-catalyzed Pictet-Spengler reaction Of D-tryptophan methyl ester with piperonal in acetic acid has been reported, the best stereo selectivity (cis/trans = 92:8) was obtained with benzoic acid as the catalyst. The Pictet-Spengler reaction Of D-tryptophan methyl ester hydrochloride with piperonal in various solvents has been extensively studied, the solvent-dependence of stereoselectivities could be principally attributed to the solubility-difference between cis and trans products 5-HCl in the used solvent, the best stereoselectivity (cis/trans = 99: 1) was obtained using nitromethane or acetonitrile as the solvent. A base-catalyzed epimerization at 12a-position of Cialis 1 (tadalafil) in a DMSO-containing solvent was also exploited. Cialis, 12a-epi-Cialis 2, deuterium-labeled 3,3,12a-d(3)-Cialis 3, and 3,3,12a-d(3)-12a-epi-Cialis 4 were efficiently synthesized from D-tryptophan methyl ester hydrochloride. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.017