1-(S)-isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester | 1042980-72-2

• 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: 1-(S)-isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester
• 英文别名: (S)-tert-butyl 1-isopropyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate；tert-butyl (1S)-1-propan-2-yl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
• CAS: 1042980-72-2
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: ZXYJQTFFAGAOIB-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(S)-isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester 在 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1-(S)-isopropyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]-quinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective total synthesis of (S)-(−)-quinolactacin B

  摘要：

  The enantioselective total synthesis of (-)-quinolactacin B (-)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-beta-carboline 2. Based on Noyori's work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-beta-carbolines possessing the (S) absolute configuration, the corrected asymmetric center of the natural product. The synthetic quinolactacin B displayed optical rotations that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural quinolactacin B. The final product's stereochemical assignment is in agreement with that proposed by Nakagawa and co-workers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.130
• 作为产物：
  描述：

  2-(1H-indol-3-yl)-N-(naphthalen-1-ylmethyl)ethanamine 在 (S)-6,6'-di(naphthalen-1-yl)-1,1'-spirobiindane-7,7'-diyl phosphate 、 10% Pd(OH)₂ on C 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 10.08h， 生成 1-(S)-isopropyl-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  SPINOL-磷酸催化的高对映选择性Pictet-Spengler反应

  摘要：

  手性SPINOL-磷酸是N b -α-萘甲基甲基色胺与一系列脂族和芳族醛的不对称Pictet-Spengler反应的高度对映选择性催化剂，可提供具有优异收率和ee值的旋光四氢-β-咔啉。当前协议已应用于（-）-甜菜碱的不对称总合成中。

  DOI：

  10.1002/chem.201103207

文献信息

• Highly Enantioselective Pictet-Spengler Reaction Catalyzed by SPINOL-Phosphoric Acids
  作者：Dan Huang、Fangxi Xu、Xufeng Lin、Yanguang Wang

  DOI：10.1002/chem.201103207

  日期：2012.3.12

  enantioselective catalysts for the asymmetric Pictet–Spengler reaction of Nb‐α‐naphthylmethyl tryptamines with a series of aliphatic and aromatic aldehydes, affording optically active tetrahydro‐β‐carbolines in excellent yields and ee values. The current protocol has been applied in the asymmetric total synthesis of (−)‐harmicine.

  手性SPINOL-磷酸是N b -α-萘甲基甲基色胺与一系列脂族和芳族醛的不对称Pictet-Spengler反应的高度对映选择性催化剂，可提供具有优异收率和ee值的旋光四氢-β-咔啉。当前协议已应用于（-）-甜菜碱的不对称总合成中。
• Enantioselective total synthesis of (S)-(−)-quinolactacin B
  作者：Nagula Shankaraiah、Wender A. da Silva、Carlos Kleber Z. Andrade、Leonardo Silva Santos

  DOI：10.1016/j.tetlet.2008.04.130

  日期：2008.6

  The enantioselective total synthesis of (-)-quinolactacin B (-)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-beta-carboline 2. Based on Noyori's work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-beta-carbolines possessing the (S) absolute configuration, the corrected asymmetric center of the natural product. The synthetic quinolactacin B displayed optical rotations that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural quinolactacin B. The final product's stereochemical assignment is in agreement with that proposed by Nakagawa and co-workers. (C) 2008 Elsevier Ltd. All rights reserved.