(1RS)-1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline | 255861-05-3

• 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: (1RS)-1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline
• 英文别名: 1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline；1-(2,2-dimethoxyethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 255861-05-3
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: LCCYWXDTIXBLKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1RS)-1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline 在 盐酸 、 4-甲基苯磺酸吡啶 作用下， 以 氯仿 、 水 为溶剂， 反应 72.0h， 生成 (1R)-1-(2',2'-dimethoxyethyl)-1,2,3,4-tetrahydro-β-carboline
  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：

  色胺 、 1,1,3,3-四甲氧基丙烷 在 盐酸 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 45.0h， 以75%的产率得到(1RS)-1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline
  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

• Tietze, Lutz-F.; Bachmann, Juergen; Schul, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 7, p. 983 - 985
  作者：Tietze, Lutz-F.、Bachmann, Juergen、Schul, Wolfgang

  DOI：——

  日期：——
• Easy generation of an enantiopure general indolalkaloid building block by kinetic resolution
  作者：Ming Zhao、Chao Wang、Shiqi Peng、Ekkehard Winterfeldt

  DOI：10.1016/s0957-4166(99)00412-7

  日期：1999.10

  On treatment of racemic 1-(2,2-dimethoxyethyl)-1,2,3,4-tetrahydrocarboline 7 with Boc-L-Ala and DCC the (1S)-enantiomer (1S)-7 reacted much faster than (1R)-7 and gave rise to 1-(2,2-dimethoxyethyl)-2-(N-t-Boc-L-alanyl)-1,2,3,4-tetrahydrocarboline. The untouched (1R)-enantiomer (1R)-7 could be reisolated in enantiopure form. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• 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.