2-[(1S,2S,4S)-双环[2.2.1]庚-5-烯-2-基]乙胺 | 61863-41-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-[(1S,2S,4S)-双环[2.2.1]庚-5-烯-2-基]乙胺
• 英文名称: 5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene
• 英文别名: endo-5-aminoethylbicyclo[2.2.1]hept-2-ene；endo-5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene；2-(bicyclo[2.2.1]hept-5-en-endo-2-yl)ethanamine；2-[(1S,2S,4S)-Bicyclo[2.2.1]hept-5-EN-2-YL]ethanamine；2-[(1S,2S,4S)-2-bicyclo[2.2.1]hept-5-enyl]ethanamine
• CAS: 61863-41-0
• 化学式: C₉H₁₅N
• 分子量: 137.225
• InChiKey: IGRYFUUCWNBVDN-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(1S,2S,4S)-双环[2.2.1]庚-5-烯-2-基]乙胺 在 sodium hydroxide 、 双氧水 作用下， 以 乙醚 、 氯仿 、 水 为溶剂， 生成 exo-2,3-epoxy-5-[2-(p-nitrophenylsulfonylamino)ethyl]bicyclo[2.2.1]heptane
  参考文献：
  名称：

  5-（2-氨基乙基）双环[2.2.1]庚-2-烯衍生物的合成和环氧化

  摘要：

  A number of derivatives of 5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene (85-90% of the endo isomer) were synthesized by reactions with p-nitrobenzenesulfonyl chloride, p-toluenesulfonyl chloride, benzoyl chloride, p-nitrobenzoyl chloride, benzyl isocyanate, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride. By reactions of the resulting sulfon- and carboxamides with peroxyphthalic acid generated in situ from phthalic anhydride and 40-4.% hydrogen peroxide the corresponding epoxy derivatives were obtained. These reactions were not accompanied by heterocyclization into azabrendane derivatives, which is typical of homologous N-(p-nitrophenylsulfonyl)-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene.

  DOI：

  10.1023/a:1015338305344
• 作为产物：
  描述：

  二环[2.2.1]庚-5-烯-2-乙酰腈,(1R,2R,4R)-rel- 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.5h， 以83%的产率得到2-[(1S,2S,4S)-双环[2.2.1]庚-5-烯-2-基]乙胺
  参考文献：
  名称：

  刚性[N]-聚降冰片烷衍生的双功能嵌入剂对DNA的分子识别：合成和评估其结合特性。

  摘要：

  我们已经在DNA识别的背景下利用了多价的概念，使用新颖的化学方法来合成具有异常序列选择性的新型bis-intercalator。先前已经观察到双插入，但是用于这种分子的从头构建的设计原理是未知的。我们的化合物具有两个从刚性，基于聚降冰片烷的支架中突出的芳族基团。骨架的长度和特征以及嵌入剂的身份各不相同，从而导致双螺旋的单价或二价识别具有不同的亲和力。我们的先导化合物被证明是中等序列选择性的双嵌入剂，展开角度为27度，结合常数约为8 microM。9-氨基ac啶环比over啶羧酰胺或萘二甲酰亚胺更可取，刚性的[3]-聚降冰片烷支架优于[5]-聚降冰片烷。连接环与支架的连接子的柔性，尽管影响较小，但会影响DNA结合的强度和特性。

  DOI：

  10.1021/jm0613020

文献信息

• NOVEL INDOLE DERIVATIVES AND THEIR USE IN NEURODEGENERATIVE DISEASES
  申请人：Merck Patent GmbH

  公开号：US20160168090A1

  公开（公告）日：2016-06-16

  The present invention relates to indole compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of P2X7, and for the treatment of P2X7-related disorders.

  本发明涉及吲哚化合物及其药用可接受的组合物，用作P2X7拮抗剂，用于治疗与P2X7相关的疾病。
• Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions
  作者：James C. Knight、Susan Richter、Melinda Wuest、Jenilee D. Way、Frank Wuest

  DOI：10.1039/c3ob40548f

  日期：——

  evaluated its ability to undergo strain-promoted copper-free click chemistry reactions with two model tetrazine species: an asymmetric dipyridyl tetrazine derivative (Tz) and a tetrazine thiourea-coupled stabilised bombesin peptide (TT-BBN). In both cases, [181818F]NFB was found to undergo rapid and high-yielding click chemistry reactions. Furthermore, as reactions of this type could also potentially be used

  之间的无铜点击化学反应 降冰片烯众所周知，四嗪类物质可以在温和的条件下以快速，可靠和选择性的方式进行。由于这些吸引人的性质，最近已经将该反应作为生物缀合的普遍适用方法进行了研究。在这里，我们报告了一种针对新型18 F标记的降冰片烯衍生物（[ 18 1818F] NFB）的便捷合成方法，并评估了其与两种模型四嗪类化合物进行应变促进的无铜点击化学反应的能力：不对称的二吡啶基四嗪衍生物（Tz）和四嗪硫脲偶联的稳定蛙皮素肽（TT-BBN）。在这两种情况下，[ 18 1818F] NFB被发现经历了快速和高产量的点击化学反应。此外，由于这种类型的反应也可能在体内用于促进肿瘤成像和治疗的新型预靶向方法的开发，因此我们还评估了[ 18]的放射药理学特征（生物利用度，生物分布，血液清除率和代谢稳定性）。1818F] NFB在正常BALB / c小鼠中。这种放射性标记的化合物具有很高的生物利用度和代谢稳定性
• Reactions of Bi-, Tri-, and tetracyclic amines with succinic anhydride
  作者：L. I. Kas’yan、A. V. Serbin、A. O. Kas’yan、D. V. Karpenko、E. A. Golodaeva

  DOI：10.1134/s1070428008030056

  日期：2008.3

  Succinic anhydride reacted with cage-like amines bicyclo[2.2.1]hept-5-en-exo-and-endo-2-yl-methanamines, 2-(bicyclo[2.2.1]hept-5-en-endo-2-yl)ethanamine, exo-5,6-epoxybicyclo[2.2.1]heptan-exo-2-yl-methanamine, tetracyclo[6.2.1.13,6.02,7]dodec-9-en-endo-4-ylmethanamine, 1-(bicyclo[2.2.1]heptan-2-yl)ethanamine, and 4-azatricyclo[5.2.1.02,6]dec-8-ene} to give the corresponding amido acids having a cage-like fragment. The latter were converted into carboximides by the action of hexamethyldisilazane in boiling benzene in the presence of zinc(II) chloride and then into epoxy derivatives. The structure of the newly synthesized compounds was confirmed by IR and NMR spectroscopy.

  琥珀酸酐与笼状胺反应，生成具有笼状结构的相应酰胺酸。后者在氯化锌存在下，在沸腾的苯中经六甲基二硅氮烷的作用转化为羧亚胺，然后转化为环氧衍生物。新合成的化合物的结构通过红外光谱和核磁共振光谱得到证实。
• Indole derivatives and their use in neurodegenerative diseases
  申请人：Merck Patent GmbH

  公开号：US10323000B2

  公开（公告）日：2019-06-18

  The present invention relates to indole compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of P2X7, and for the treatment of P2X7-related disorders.

  本发明涉及作为 P2X7 拮抗剂和用于治疗 P2X7 相关疾病的吲哚化合物及其药学上可接受的组合物。
• ——
  作者：A. O. Kas'yan、E. A. Golodaeva、A. V. Tsygankov、L. I. Kas'yan

  DOI：10.1023/a:1022553832553

  日期：——

  Reactions of p-nitrophenyloxirane with amines containing fragments with bicyclic skeleton of norbornene, norbornane, epoxynorbornane (stereoisomeric exo- and endo-5-an-aminomethylbicyclo[2.2.1]hept-2-enes, N-benzyl-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene, endo-5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene, stereoisomeric exo- and endo-2-aminomethylbicyclo[2.2.1]beptanes, 2-(1-aminoethyl)bicyclo[2.2.1]heptane, exo-5-aminomethyl-exo-2,3-epoxybicyclo[2.2.1]heptane) were investigated. The aminolysis of p-nitrophenyloxirane occurred regioselectively according to Krasusky rule as was proved by H-1 and C-13 NMR data. As shown by H-1 and C-13 NMR spectroscopy the oxyalkylation product obtained from N-benzyl-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene was composed of two diastereomers originating from the presence of a chiral nitrogen atom in the rear part of the rigid bicyclic skeleton. New products of amino groups transformation in the molecules of hydroxyamines were obtained by reaction with p-methylbenzoyl chloride and p-nitrophenylsulfonyl chloride. Regioselectivity of the attack of electrophilic reagents on the nitrogen in the hydroxyamines was confirmed by IR and H-1 NMR spectra of the products. The data on pharmacological activity tests of N-2-hydroxyethyl(p-nitrophenyl)-5-aminomethylbicyclo[2.2.1]hept-2-ene are reported.