N-aminobicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide | 38253-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-aminobicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide
• 英文别名: (1R,2S,6R,7S)-4-amino-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 38253-40-6
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: NONAXZPAOYXUOC-UMRXKNAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-aminobicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide 在 甲酸 、 三苯胂 、 palladium diacetate 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 N,N’-bis[5-phenylbicyclo[2.2.1]heptane-2-endo,3-endo-dicarboximide]
  参考文献：
  名称：

  Gul, Melek; Kulu, Irem; Gunkara, Omer Tahir, Acta Chimica Slovenica, 2013, vol. 60, # 1, p. 87 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 一水合肼 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 N-aminobicyclo[2.2.1]hept-5-ene-2-endo,3-endo-dicarboximide
  参考文献：
  名称：

  Hydroarylation Reactions of N-Acylaminosubstituted Tricyclic Imides

  摘要：

  钯催化的不饱和 N-酰氨基取代的三环亚胺的加氢反应提供了一种新的外芳基（杂芳基）取代的三环 N-酰氨基亚胺的立体选择性合成方法。

  DOI：

  10.3184/174751913x13686357345579

文献信息

• An Investigation into Domino-Heck Reactions ofN-Acylamino-Substituted Tricyclic Imides: Synthesis of New Prospective Pharmaceuticals
  作者：Emine Bagdatli、Nüket Öcal、Dieter E. Kaufmann

  DOI：10.1002/hlca.200790244

  日期：2007.12

  Heck and domino-Heck reactions of unsaturated N-acylamino-substituted tricyclic imides with aryl(heteroaryl) iodides and phenyl- or (trimethylsilyl)acetylene were either carried out in the presence of formate or phenyl- and (trimethylsilyl)acetylene, respectively. The CC coupling reactions appeared to be completely diastereoselective, giving the corresponding N-acylamino-5-exo-aryl (heteroaryl)- (5a–c

  不饱和N-酰基氨基取代的三环酰亚胺与芳基（杂芳基）碘化物和苯基或（三甲基甲硅烷基）乙炔的Heck和Domino- Heck反应分别在甲酸酯或苯基和（三甲基甲硅烷基）乙炔的存在下进行。CC偶联反应似乎是完全非对映选择性的，得到相应的N-酰基氨基-5- exo-芳基（杂芳基）-（5a – c，6a，b），N-（苯甲酰基氨基）-5- exo-苯基-6- exo -[（三甲基甲硅烷基）乙炔基]-（5d）或5- exo-（4-氯苯基）-N-（2，2-二甲基丙酰基氨基）-6-外-（苯基乙炔基）双环[2.2.1]庚烷-2-内酯，3-内-二甲叉酰亚胺（6c）（方案3和4）。
• Structure and Reactivity of Bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) Acid Hydrazide
  作者：L.I. Kas'yan、I.N. Tarabara、Ya.S. Bondarenko、S.V. Shishkina、O.V. Shishkin、V.I. Musatov

  DOI：10.1007/s11178-005-0305-9

  日期：2005.8

  Establishing of the structure of hydrazinolysis product obtained from bicyclo[2.2.1]hept-2-ene-endo-5, endo-6-dicarboxylic (endic) acid was performed by preparation of the compound under alternative conditions followed by comparison of the characteristics and spectral parameters of the resulting substances, and also by quantum-chemical calculations by the density functional method of the chemical shifts in 1H and 13C NMR spectra of different reaction products. The X-ray diffraction analysis of the hydrazide was also carried out. The compound obtained was assigned a structure of N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide. The products were prepared by its reactions with arylsulfonyl chlorides, benzoyl chlorides, m-tolyl and p-toluene-sulfonyl isocyanates, phenyl isothiocyanate, with o-nitrobenzaldehyde, and oxiranes (1,2-epoxycyclohexane and 2,3-epoxypropylcarbazole). The aromatic sulfonamides, carboxamides, and ureas were epoxidized by performic acid obtained in situ from the formic acid and hydrogen peroxide. Products of [3+2]-cycloaddition of aryl azides to the strained double bond in the N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide and its derivatives. The structures of compounds obtained were confirmed by their IR, 1H and 13C NMR spectra.

  从双环[2.2.1]庚-2-烯-内-5,内-6-二羧酸（endic酸）获得的肼解产物的结构确立是通过在不同条件下合成该化合物，随后比较所得到物质的特性和光谱参数，以及采用密度泛函方法进行量子化学计算，分析不同反应产物在1H和13C NMR光谱中的化学位移。同时还进行了该肼类化合物的X射线衍射分析。所获得的化合物被确定为N-氨基双环[2.2.1]庚-2-烯-内-5,内-6-二羧亚胺。该化合物与芳基磺酰氯、苯甲酰氯、m-甲基苯磺酰异氰酸酯、对甲苯磺酰异氰酸酯、苯异硫氰酸酯、o-硝基苯甲醛和环氧化物（1,2-环氧环己烷和2,3-环氧丙基咔唑）反应得到各类产物。芳香族磺胺、羧酰胺和脲类化合物通过在原位生成的过形式酸进行环氧化处理。合成的N-氨基双环[2.2.1]庚-2-烯-内-5,内-6-二羧亚胺及其衍生物与芳基叠氮化合物的[3+2]环加成反应的产物也得到了报道。所得化合物的结构通过其红外光谱、1H和13C NMR光谱得到了确认。
• Heck-type hydroarylations and 1,3-dipolar cycloaddition reactions of new tricyclic hydrazones
  作者：Melek Gul、Nuket Ocal

  DOI：10.1139/v09-179

  日期：2010.4

  The C–C coupling of the new tricyclic hydrazones 3–7 with aryl and heteroaryl halides gave under reductive Heck conditions the tricyclic 1-(arylideneamino)pyrolidine-2,5-diones 8–11a, 9–11b, 10c, and 12. The [3+2] cycloadditions of 3–7 with p-chlorophenyl nitrile oxide (13) yielded the bridged isoxazoline derivatives 14–18 with potential biological activity.

  在还原 Heck 条件下，新的三环肼 3-7 与芳基和杂芳基卤化物进行 C-C 偶联，得到了三环 1-（芳基亚氨基）吡咯烷-2,5-二酮 8-11a、9-11b、10c 和 12。3-7 与对氯苯腈氧化物（13）发生[3+2]环加成反应，得到了具有潜在生物活性的桥接异噁唑啉衍生物 14-18。
• Synthesis of new N-norbornylimide substituted amide derivatives, their reductive Heck and domino Heck reactions
  作者：Fatma Albayrak、Omer Tahir Gunkara、Elif Basak Ersoy、Nuket Ocal、Dieter Eckhard Kaufmann

  DOI：10.24820/ark.5550190.p010.304

  日期：——

  Palladium-catalyzed, regioselective hydroarylation reactions of N-norbornenylimide substituted amides were studied to synthesize pentanamide derivatives containing exo-aryl-substituted norbornyl imide groups in excellent yields. All newly synthesized derivatives have been characterized by FTIR, H, C NMR, GC/MS and TOF/Qtof analyses.

  研究了钯催化的 N-降冰片烯酰亚胺取代酰胺的区域选择性加氢芳基化反应，以优异的产率合成含有外芳基取代的降冰片酰亚胺基团的戊酰胺衍生物。所有新合成的衍生物均已通过 FTIR、H、C NMR、GC/MS 和 TOF/Qtof 分析进行表征。
• Reactions of 4-amino-4-azatricyclo[5.2.1.02,6-endo ]dec-8-ene-3,5-dione with dicarboxylic acid anhydrides
  作者：L. I. Kas’yan、I. N. Tarabara、Ya. S. Bondarenko、L. K. Svyatenko、A. V. Bondarenko

  DOI：10.1134/s1070428007070135

  日期：2007.7

  Reactions of 4-amino-4-azatricyclo[5.2.1.0(2,6-endo)]dec-8-ene-3,5-dione (hydrazinolysis product of endic anhydride) with succinic, maleic, cis-cyclohexane-1,2-dicarboxylic, endic, phthalic, and 1,8-naphthalic anhydrides were studied. Procedures for the preparation of the corresponding hydrazido acids and bis-imides were proposed. Their reactions with peroxyformic acid, depending on the substrate nature, led to the formation of both epoxy hydrazido acids and epoxy imides. The unsaturated adducts reacted with p-nitrophenyl azide to give the corresponding triazole derivatives.