(1S,3R,4R)-2-[(S)-1-phenylethyl]-3-aminemethyl-2-azabicyclo[2.2.1]heptane | 1290085-12-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-aminemethyl-2-azabicyclo[2.2.1]heptane
• 英文别名: [(1S,3R,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptan-3-yl]methanamine
• CAS: 1290085-12-9
• 化学式: C₁₅H₂₂N₂
• 分子量: 230.353
• InChiKey: VZUATBHEHMNOTC-ATGSNQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-aminemethyl-2-azabicyclo[2.2.1]heptane 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-[(2-naphthylmethyl)aminomethyl]-2-azabicyclo[2,2,1]heptane
  参考文献：
  名称：

  New 2-azanorbornyl derivatives: chiral (N,N)-donating ligands for asymmetric catalysis

  摘要：

  New chiral 2-azanorbornane derivatives were prepared and used as (N,N)-donating ligands in a copper-catalyzed Henry reaction yielding up to 62% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.011
• 作为产物：
  描述：

  ethyl <(S)-1-phenylethyl>iminoethanoate 在 lithium aluminium tetrahydride 、 草酰氯 、 palladium on activated charcoal 、 盐酸羟胺 、 氢气 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-aminemethyl-2-azabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis, structure and antiproliferative activity of chiral polyamines based on a 2-azanorbornane skeleton

  摘要：

  A series of enantiopure 2-azanorbornane-based amines were prepared via a stereoselective aza-Diels-Alder reaction and further modifications of the obtained cycloadduct. In particular, derivatives containing two bicyclic moieties linked by N-C-C-N fragments were synthesized. Two dimeric derivatives exhibited a significant antiproliferative activity against selected cell lines, comparable to cisplatin in certain cases. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.009

文献信息

• Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton
  作者：Mahzeiar Samadaei、Matthias Pinter、Daniel Senfter、Sibylle Madlener、Nataliya Rohr-Udilova、Dominika Iwan、Karolina Kamińska、Elżbieta Wojaczyńska、Jacek Wojaczyński、Andrzej Kochel

  DOI：10.3390/molecules25102355

  日期：——

  A series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from aza-Diels–Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic activity of the obtained bicyclic derivatives was evaluated using human hepatocellular carcinoma (HCC), medulloblastoma (MB)

  通过将氮杂-Diels-Alder环加合物转化为基于2-氮杂降冰片烷或桥连氮杂环烷骨架的胺，然后与磺酰氯反应，制备了一系列含有2-氮杂双环烷烃支架的手性磺酰胺。使用人肝细胞癌 (HCC)、成神经管细胞瘤 (MB) 和胶质母细胞瘤 (GBM) 细胞系评估了获得的双环衍生物的细胞毒活性。与非恶性细胞相比，选定的化合物显示出显着降低细胞活力。
• Chiral pyrrolidine thioethers and 2-azanorbornane derivatives bearing additional nitrogen functions. Enantiopure ligands for palladium-catalyzed Tsuji-Trost reaction
  作者：Elżbieta Wojaczyńska、Karolina Kamińska、Jacek Wojaczyński、Jacek Skarżewski

  DOI：10.3998/ark.5550190.p009.792

  日期：——

  An efficient procedure for the synthesis of new enantiopure pyrrolidine-based sulfides bearing additional nitrogen donors and secondary amines based on a bicyclic 2-azanorbornane skeleton was developed. Their application as ligands in palladium-catalyzed Tsuji-Trost reactions led to high yields and up to 82% ee.

  开发了一种基于双环 2-氮杂降冰片烷骨架合成带有额外氮供体和仲胺的新型对映纯吡咯烷基硫化物的有效方法。它们在钯催化的 Tsuji-Trost 反应中作为配体的应用导致高产率和高达 82% 的 ee。
• Zinc complexes formed by 2,2′-bipyridine and 1,10-phenanthroline moieties combined with 2-azanorbornane: modular chiral catalysts for aldol reactions
  作者：Elżbieta Wojaczyńska、Jacek Skarżewski、Łukasz Sidorowicz、Robert Wieczorek、Jacek Wojaczyński

  DOI：10.1039/c6nj02251k

  日期：——

  Chiral scaffolds of 2-azabicyclo[2.2.1]heptane and 2-azabicyclo[3.2.1]octane were used for the construction of new modular catalysts containing complexing moieties pyridine, 2,2′-bipyridine and 1,10-phenanthroline appended by an imine linkage. The coordination abilities of the new ligands towards Zn(II) were investigated using NMR and UV spectroscopy. The plausible structures of the [ZnL2]2+ and [ZnLXn](2−n)+

  2-氮杂双环[2.2.1]庚烷和2-氮杂双环[3.2.1]辛烷的手性支架用于构建新的模块催化剂，该催化剂包含配位吡啶，2,2'-联吡啶和1,10-菲咯啉亚胺键。利用NMR和UV光谱研究了新配体对Zn（II）的配位能力。通过比较实验和DFT计算的NMR光谱，可以确定形成的[ZnL 2 ] 2+和[ZnLX n ] （2- n）+配合物的合理结构。[ZnLX n ] （2- n）+的催化应用在与芳族醛酮的不对称醛醇缩合反应型复合物所产生的过量的相应的顺式中高达> 98％ee的-aldols。
• Application of Polyamines and Amino Acid Derivatives Based on 2-Azabicycloalkane Backbone in Enantioselective Aldol Reaction
  作者：Dominika Iwan、Karolina Kamińska、Elżbieta Wojaczyńska

  DOI：10.3390/molecules26175166

  日期：——

  forming reactions, such as aldol reaction and condensation, belong to extremely desired transformations as manifested by >25,000 entries in SciFinder. Their stereoselective variant requires the use of an appropriate catalyst with a strictly defined structure. Hence, chiral 2-azabicycloalkane-based catalysts were designed, synthesized and tested in a stereoselective aldol reaction between cyclic/acyclic

  碳-碳键形成反应，如羟醛反应和缩合，属于非常需要的转化，如 SciFinder 中 >25,000 个条目所证明的那样。它们的立体选择性变体需要使用具有严格限定结构的合适催化剂。因此，设计、合成了手性 2-氮杂双环烷烃基催化剂，并在有机和水介质中环状/无环酮和对硝基苯甲醛之间的立体选择性羟醛反应中进行了测试。在含有手性双环骨架的催化剂中，基于 2-氮杂双环 [3.2.1] 辛烷和吡咯烷单元的酰胺表现出最好的催化活性，并以优异的化学产率（高达 95%）和良好的非对映选择性和对映选择性提供了羟醛产物（博士22:78，EE 高达 63%）。
• Synthesis, spectroscopic and computational studies of photochromic azobenzene derivatives with 2-azabicycloalkane scaffold
  作者：Karolina Kamińska、Dominika Iwan、Alex Iglesias-Reguant、Weronika Spałek、Marek Daszkiewicz、Anna Sobolewska、Robert Zaleśny、Elżbieta Wojaczyńska、Stanisław Bartkiewicz

  DOI：10.1016/j.molliq.2022.119869

  日期：2022.10

  In this study we report the synthesis and photochromic properties of chiral azobenzene derivatives based on the 2-azabicycloalkane skeleton. The photochromic properties of newly synthesized family of azobenzene derivatives have been studied using the UV/Vis spectroscopy. The interpretation of spectral features was supported by the results of the electronic-structure calculations. The experimental data

  在这项研究中，我们报告了基于 2-氮杂双环烷烃骨架的手性偶氮苯衍生物的合成和光致变色性质。使用紫外/可见光谱研究了新合成的偶氮苯衍生物家族的光致变色性质。光谱特征的解释得到了电子结构计算结果的支持。实验数据证实 - 典型的偶氮苯 -反式-顺式和顺式-反式的出现分别用可见光和紫外光照射时的光化学反应。另一方面，观察到非典型的热弛豫过程，尤其是在紫外光照射后，这表明热逆反应并不像人们想象的那么简单。位于2-氮杂双环烷烃上的取代基导致所研究化合物的电子结构发生一些变化，反映在电子光谱中谱带形状的变化上。