trans-(+/-)-1-aminoindoloquinolizidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: trans-(+/-)-1-aminoindoloquinolizidine
• 英文别名: (1S,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-amine
• 化学式: C₁₅H₁₉N₃
• 分子量: 241.336
• InChiKey: RISHEOUOTOHERH-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  45
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 trans-(+/-)-1-aminoindoloquinolizidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以74%的产率得到(1R,12bR)-(1,2,3,4,6,7,12,12b-Octahydro-indolo[2,3-a]quinolizin-1-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereochemistry of Electrosprayed Ions. Indoloquinolizidine Derivatives

  摘要：

  Energy-resolved mass spectrometry (ERMS) using electrospray ionization and in-source collisional activation is a very promising approach to structural investigations of positional isomers and stereoisomers. This method was applied successfully in the case of two stereoisomeric aminoindoloquinolizidines. Comparison of electrospray/ERMS with several scanning modes including high-energy tandem mass spectrometry was made. Schematically, the high collision-energy regime led to fingerprints of both the isomers investigated but was totally insensitive to their stereochemical differences. The unimolecular dissociations of the protonated molecules monitored by various scan modes were satisfactory with regard to stereochemical differentiation, but without any control of the internal energy level of the precursor ions. In contrast, electrospray ionization provided easy and precise control of the energy deposition by varying the sampling cone voltage. Simple comparison of the breakdown curves, obtained by changing the potential difference between the sampling cone and the skimmer of the ion source, revealed the stereochemical dependence of different fragmentation pathways. These results demonstrate that the electrospray ion source represents a simple, sensitive and inexpensive method for performing low-energy collision-induced dissociation experiments and compares very well with more sophisticated methods such as tandem mass spectrometry.

  DOI：

  10.1002/(sici)1096-9888(199610)31:10<1149::aid-jms408>3.0.co;2-i
• 作为产物：
  描述：

  L-焦谷氨酸 在 palladium on activated charcoal sodium tetrahydroborate 、 甲酸铵 、 sodium 、 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 正丁醇 为溶剂， 生成 trans-(+/-)-1-aminoindoloquinolizidine
  参考文献：
  名称：

  A new diastereoselective synthesis of (±) cis 1-aminoindoloquinolizidine

  摘要：

  An unexpected Bischler-Napieralski reaction between tryptamine and pyroglutamic acids led to a new diastereoselective access to 1-aminoindolo[2,3-a]quinolizidine 1.

  DOI：

  10.1016/s0040-4039(00)60682-2

文献信息

• Synthesis of the Indolo[2,3-a]quinolizidine Ring through the Addition of 2-Siloxyfurans to Imines and Intrinsic Reaction Coordinate Calculations
  作者：Leonardo Santos、Yaneris Mirabal-Gallardo、Maria Soriano、Julio Caballero、Jans Alzate-Morales、Mario Simirgiotis

  DOI：10.1055/s-0031-1289631

  日期：2012.1

  A concise asymmetric diastereoselective strategy for the synthesis of indolo[2,3-a]quinolizidine derivative 1 was developed using diastereoselective addition of 2-siloxyfurans 4 to imine 3 through chiral auxiliary induction. The addition of an ionic liquid as additive in the reaction favored the anti configuration in the major adduct. The stereochemical outcome of the anti/syn (threo/erythro) selectivity

  提出了一种简单的不对称非对映选择性策略，用于合成吲哚[2,3- a ]喹啉嗪衍生物1，方法是通过手性辅助诱导将2-甲硅烷氧基呋喃4非对映选择性加成到亚胺3上。在反应中添加离子液体作为添加剂有利于主要加合物的反构型。抗/合成（苏氨酸/赤霉素）的立体化学结果。DFT（B3LYP）和MP2理论根据过渡态和IRC计算合理化了选择性。在这些系统中，MP2计算被证明是选择的方法，在添加4到3的反过渡状态下观察到了轨道失对称，并且次级轨道相互作用使我们能够合理地制造主要的抗加合物6。此外，该工作还表明2-（三异丙基甲硅烷氧基）呋喃（4a）是这种曼尼希反应中选择的亲核试剂。此外，该策略的特征在于利用Mitsunobu反应将具有正确构型的氨基插入胺2中，关键中间实现1。该合成途径也可用于有前景的氮杂-β-咔啉化合物的全合成。 氮杂环丁烷-β-咔啉-手性助剂-Mitsunobu反应-本征反应坐标计算
• Chiral Synthesis of <i>trans</i>-1-Aminoindolo[2,3-<i>a</i>]quinolizidine and <i>trans</i>-1-Aminobenzo[<i>a</i>]quinolizidine Derivatives from <scp>l</scp>-Pyroglutamic Acid
  作者：Yong Sup Lee、Dae Joo Cho、Sun Nam Kim、Jung Hoon Choi、Hokoon Park

  DOI：10.1021/jo9911950

  日期：1999.12.1
• A short diastereoselective synthesis of 1-aminoindolo-[2,3-a]quinolizidines via an N-acyliminium ion cyclisation
  作者：Pierre Ducrot、Claude Thal

  DOI：10.1016/s0040-4039(99)01922-x

  日期：1999.12

  trans 1-Aminoindolo[2,3-a]quinolizidines were synthesised using an intramolecular Pictet-Spengler-like reaction. Starting from commercially available N-Cbz-L-glutamic acid, indoloquinolizidines were obtained in only five steps with good yields. This improved synthesis is the result of both a highly regioselective imide reduction and a highly diastereoselective reaction using N-acyliminium ions. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.