(1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione

• 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: (1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
• 英文别名: (3aR,4S,7R,7aS)-2-methyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione；(1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: WHRYLXXHLFPFNZ-KVFPUHGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到(1R,2R,6S,7S)-4-methyl-4-azatricyclo[5.2.1.02,6]decane-3,5-dione
  参考文献：
  名称：

  Structural Investigations into the retro-Diels-Alder Reaction. Experimental and Theoretical Studies

  摘要：

  The manifestations of the retro-Diels Alder reaction in the ground-state structures of a range of cyclopentadiene and cyclohexadiene cycloadducts 9-15 have been investigated by a combination of techniques. These include low-temperature X-ray crystallography, density functional calculations (B3LYP/ 6-31G(d,p)) on both the ground states and transition states, and the measurement of C-13-C-13 coupling constants. We have found that the carbon-carbon bonds (labeled bonds a and b), which break in the rDA, are longer in the cycloadducts 9-15 than in their corresponding saturated analogues 9s-15s, which cannot undergo the rDA reaction. The degree of carbon-carbon bond lengthening appears to be related to the reactivity of the cycloadduct, thus the more reactive benzoquinone cycloadducts 5b and 13 have longer carbon-carbon bonds, Those cycloadducts 14 and 15 which are predicted to undergo asynchronous reactions show differing degrees of carbon-carbon bond lengthening, reflecting the differing degrees of bond breaking at the calculated transition states for the rDA.

  DOI：

  10.1021/ja025634f
• 作为产物：
  描述：

  2-甲基-2-氮杂双环[2.2.1]庚-5-烯盐酸盐 在 N-甲基马来酰亚胺 作用下， 以 水 为溶剂， 反应 2.0h， 以69%的产率得到(1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
  参考文献：
  名称：

  Retro aza Diels-Alder reactions: acid catalyzed heterocycloreversion of 2-azanorbornenes in water at ambient temperature

  摘要：

  DOI：

  10.1021/ja00253a053

文献信息

• Ruthenium-Complex-Catalyzed Regio- and Stereoselective Linear Codimerization of 2-Norbornenes with Acrylic Compounds
  作者：Yasuyuki Ura、Hiroshi Tsujita、Kenji Wada、Teruyuki Kondo、Take-aki Mitsudo

  DOI：10.1021/jo050413o

  日期：2005.8.1

  A linear codimerization of 2-norbornenes with acrylic compounds such as acrylates and an acrylamide proceeded efficiently by ruthenium catalyst systems, RuCl3(tpy)/Zn (tpy = 2,2‘:6‘,2‘ ‘-terpyridine) or [RuCl2(C6H6)]2/Zn in a primary or secondary alcoholic solvent, to afford the corresponding exo-trans-2-norbornylacrylates as major products regio- and stereoselectively along with a small amount of

  通过钌催化剂体系，RuCl 3（tpy）/ Zn（tpy = 2,2'：6'，2''-叔吡啶）或[RuCl 2（C 6 H 6）] 2 / Zn在伯或仲醇溶剂中，以少量和顺式异构体的形式选择性和立体选择性地提供相应的外反式-2-降冰片基丙烯酸酯作为主要产物。2,5-降冰片二烯与丙烯酸甲酯的反应也产生了线性外-反式共聚二聚体，通过向RuCl 3中加入三芳基膦有效地催化了该反应。（tpy）/ Zn催化剂体系。
• Asymmetric Intermolecular Heck Reaction of Propargylic Acetates and Cycloalkenes to Access Fused Cyclobutenes
  作者：Zhiwei Jiao、Qi Shi、Jianrong Steve Zhou

  DOI：10.1002/anie.201708435

  日期：2017.11.13

  An intermolecular Heck reaction between propargylic acetates and cyclic olefins results in the enantioselective synthesis of highly strained cyclobutenes.

  炔丙基乙酸酯和环状烯烃之间的分子间Heck反应导致高度应变的环丁烯的对映选择性合成。
• Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous Media
  作者：Mark Lautens、John Mancuso

  DOI：10.1021/jo049874k

  日期：2004.5.1

  complex to generate a functionalized organorhodium intermediate that can cyclize onto strained olefins in good to excellent yields. The catalytic system involves the use of an electron-rich, sterically bulky ligand to stabilize the organorhodium intermediate and reduce the incidence of protodeboronation in aqueous media.

  带有侧链迈克尔型受体烯烃的芳基硼酸酯会与铑基催化络合物发生重金属化反应，生成官能化的有机铑中间体，该中间体可以良好的收率或良好的产率环化到应变烯烃上。催化体系包括使用富含电子的空间庞大的配体来稳定有机ho中间体，并减少在水性介质中原硼酸脱硼的发生率。
• Synthesis of novel fluorinated building blocks via halofluorination and related reactions
  作者：Attila Márió Remete、Tamás T Novák、Melinda Nonn、Matti Haukka、Ferenc Fülöp、Loránd Kiss

  DOI：10.3762/bjoc.16.208

  日期：——

  electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with Deoxo-Fluor®. The fluorine-containing products thus obtained were subjected to elimination reactions, yielding various fluorine-containing small-molecular entities.

  描述了一项研究，探讨了某些环状烯烃（如二酯，酰亚胺和内酰胺）的卤代氟化和氟硒化反应，它们具有不同的功能化模式和不同的结构结构。所述合成方法是基于通过环烯烃键的卤鎓离子，随后用脱氧氟核氟化亲电活化®。将如此获得的含氟产物进行消除反应，得到各种含氟小分子实体。
• Synthesis of an Electrophilic Polymer by Ring-Opening Metathesis Polymerization
  作者：C. A. Larsen、E. L. Taylor、J. N. Lambert、J. Chiefari

  DOI：10.1071/ch02067

  日期：——

  A new class of modifiable polymer is described. The electrophilic polymer is readily prepared using ring-opening metathesis polymerization (ROMP), and it is shown that amine nucleophiles can be introduced to the polymer.

  本文介绍了一类新型可改性聚合物。这种亲电聚合物很容易通过开环偏聚聚合反应（ROMP）制备出来，而且研究表明，这种聚合物可以引入胺类亲核物。