methyl (1S,3S,2'S,4'R,5'R)-1-(5'-benzoylamino-4'-methyl-1',3'-dioxane-2'-yl)-methyl-1,2,3,4-tetrahydrocarboline-3-carboxylate | 398118-92-8

• 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: methyl (1S,3S,2'S,4'R,5'R)-1-(5'-benzoylamino-4'-methyl-1',3'-dioxane-2'-yl)-methyl-1,2,3,4-tetrahydrocarboline-3-carboxylate
• 英文别名: methyl (1S,3S)-1-[[(2S,4R,5R)-5-benzamido-4-methyl-1,3-dioxan-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 398118-92-8
• 化学式: C₂₆H₂₉N₃O₅
• 分子量: 463.533
• InChiKey: QYOISSRRLVMUDE-IQGNASQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 methyl (1S,3S,2'S,4'R,5'R)-1-(5'-benzoylamino-4'-methyl-1',3'-dioxane-2'-yl)-methyl-1,2,3,4-tetrahydrocarboline-3-carboxylate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以85 mg的产率得到Methyl (1S,3S)-1-(2,2-Dimethoxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
  参考文献：
  名称：

  Diasteroselective Cyclizations with Enantiopure Malonaldehyde Monocycloacetals

  摘要：

  The synthesis of a series of enantiopure malonaldehyde monocycloacetals is described. Treatment of 8b with L-tryptophan methyl ester, 5-methoxytryptamine, and tryptamine, respectively, in the Pictet-Spengler condensation gave the corresponding enantiomerically pure key precursors 1-3 and 17-21 in only two steps. Using a chiral amino-diol successfully realized the kinetic resolution of racemic carbolines 23 and 24.

  DOI：

  10.1021/jo0057351
• 作为产物：
  描述：

  [(2S,4R,5R)-N-2-(2,2-dimethoxyethyl)-4-methyl-1,3-dioxan-5-yl]benzamide 在 草酸 、 silica gel 、 sodium sulfate 作用下， 以 氯仿 为溶剂， 反应 60.0h， 生成 methyl (1S,3S,2'S,4'R,5'R)-1-(5'-benzoylamino-4'-methyl-1',3'-dioxane-2'-yl)-methyl-1,2,3,4-tetrahydrocarboline-3-carboxylate
  参考文献：
  名称：

  Diasteroselective Cyclizations with Enantiopure Malonaldehyde Monocycloacetals

  摘要：

  The synthesis of a series of enantiopure malonaldehyde monocycloacetals is described. Treatment of 8b with L-tryptophan methyl ester, 5-methoxytryptamine, and tryptamine, respectively, in the Pictet-Spengler condensation gave the corresponding enantiomerically pure key precursors 1-3 and 17-21 in only two steps. Using a chiral amino-diol successfully realized the kinetic resolution of racemic carbolines 23 and 24.

  DOI：

  10.1021/jo0057351

文献信息

• Diasteroselective Cyclizations with Enantiopure Malonaldehyde Monocycloacetals
  作者：Lanrong Bi、Ming Zhao、Chao Wang、Shiqi Peng、Ekkehard Winterfeldt

  DOI：10.1021/jo0057351

  日期：2002.1.1

  The synthesis of a series of enantiopure malonaldehyde monocycloacetals is described. Treatment of 8b with L-tryptophan methyl ester, 5-methoxytryptamine, and tryptamine, respectively, in the Pictet-Spengler condensation gave the corresponding enantiomerically pure key precursors 1-3 and 17-21 in only two steps. Using a chiral amino-diol successfully realized the kinetic resolution of racemic carbolines 23 and 24.