5,6-benzobicyclo<2.2.2>octen-2-one | 13153-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,6-benzobicyclo<2.2.2>octen-2-one
• 英文别名: benzobicyclo<2.2.2>octen-2-one；benzobicyclo<2.2.2>octenone；2-Oxo-benzobicyclo-[2.2.2]-octen；1,4-Ethanonaphthalen-2(1H)-one, 3,4-dihydro-；tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-one
• CAS: 13153-76-9；28976-60-5；29073-66-3
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: JTAWEGXLKGECMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-benzobicyclo<2.2.2>octen-2-one 在 哌啶 、 碘 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 25.0h， 生成 2-methyl-5,6-benzobicyclo<2.2.2>octa-2,5-diene
  参考文献：
  名称：

  Electronic control of stereoselectivity. 9. The stereochemical course of electrophilic additions to aryl-substituted benzobicyclo[2.2.2]octadienes

  摘要：

  DOI：

  10.1021/ja00414a015
• 作为产物：
  描述：

  1,4-二氢-1,4-乙基桥萘 在 pyridinium chlorochromate 作用下， 生成 5,6-benzobicyclo<2.2.2>octen-2-one
  参考文献：
  名称：

  Organic photochemistry. 63. Photolytic cleavage of remote functional groups in polyfunctional molecules. Photolysis of exo- and endo-benzobicyclo[2.2.2]octen-2-yl chloride

  摘要：

  DOI：

  10.1021/jo00367a020

文献信息

• Sulphonamido-substituted bridged bicycloalkyl derivatives
  申请人：——

  公开号：US20040029862A1

  公开（公告）日：2004-02-12

  A class of compounds is disclosed, comprising sulphonamido-substituted bridged bicycloalkyl structures. The compounds are inhibitors of gamma-secretase, and hence are useful in the treatment of and/or prevention of Alzheimer's disease.

  揭示了一类化合物，包括磺胺基取代的桥联双环烷基结构。这些化合物是γ-分泌酶的抑制剂，因此在治疗和/或预防阿尔茨海默病方面是有用的。
• NOVEL CANNABINOID RECEPTOR LIGANDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESSES FOR THEIR PREPARATION
  申请人：Muthuppalaniappan Meyyappan

  公开号：US20080200501A1

  公开（公告）日：2008-08-21

  The present invention relates to novel cannabinoid receptor modulators, in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2) receptor modulators, and uses thereof for treating diseases, conditions and/or disorders modulated by a cannabinoid receptor (such as pain, neurodegenative disorders, eating disorders, weight loss or control, and obesity).

  本发明涉及新型大麻素受体调节剂，特别是大麻素1（CB1）或大麻素2（CB2）受体调节剂，以及它们用于治疗受大麻素受体调节的疾病、症状和/或紊乱（如疼痛、神经退行性疾病、进食紊乱、体重减轻或控制以及肥胖）的用途。
• Unexpected effect of an hydroxyl group on π-facial selectivity in the nucleophilic addition to bicyclo[2.2.2]octan-2-ones
  作者：Jean-François Devaux、Pierre Fraisse、Issam Hanna、Jean-Yves Lallemand

  DOI：10.1016/0040-4039(95)02032-2

  日期：1995.12

  An unprecedented remote effect of the hydroxyl group on π-facial selectivity was observed in the addition of Grignard reagents to bicyclo[2.2.2]octan-2-ones, where nucleophilic attack occured from the slerically more hindered face.

  在双环[2.2.2] octan-2-ones中添加格氏试剂后，观察到羟基对π面选择性的前所未有的遥远影响，亲核性攻击是由受阻较严重的面部发生的。
• Ring-strain effects on the efficiencies and deuterium effects on the efficiencies and regioselectivities of the di-π-methane rearrangement of bicyclic systems
  作者：Helfried Hemetsberger、Frank Nispel

  DOI：10.1016/s0040-4020(01)90518-6

  日期：1990.1

  synthesized and irradiated under sensitized conditions. The compounds 12 - 15 yielded di-π-methane rearrangement products. 16 was not reactive. The quantum yields for product formation were measured. They increase with ring strain of the bicyclic systems. A kinetic isotope effect on the regiospecifity of the rearrangement was observed in all cases. In addition, an isotope effect on the quantum yields of

  的protio-和单vinyldeuterated benzobicyclo（n.2.2]烯烃（n = 1至4）12 - 13和15 - 16和1,2-二cyclopropabenzobarrelene 14被合成并致敏条件下照射的化合物。12 - 15产生二-π甲烷重排产物。16没有反应性的。测定产物形成的量子产率，它们增加了与双环体系的环应变。甲动力学同位素效应上在所有情况下观察到了重排的regiospecifity。此外，在13和15中观察到同位素对产物形成的量子产率的影响。
• Substituent effects on the efficiencies and regioselectivities of the di-π-methane rearrangement of vinyl-substituted bicyclic systems
  作者：Helfried Hemetsberger、Matthias Nobbe

  DOI：10.1016/s0040-4020(01)85094-8

  日期：1988.1

  - which were mono- or disubstituted at the vinyl moiety were synthesized. The substituent effects on the efficiencies and regioselectivities of the di-π-methane rearrangement were studied with the results: 1) The dihydrobenzobarrelene system rearranges less efficiently than the 7,7-benzonorbornadiene system. 2) The effect of the substituents on the efficiencies is more pronounced in the less efficient

  Dihydrobenzobarralenes -和7,7- dimethylbenzonorbornadienes -合成了在乙烯基部分被单或双取代的化合物。研究了取代基对二-π-甲烷重排效率和区域选择性的影响，结果表明：1）二氢苯并三氢戊烯烯系统的重排效率低于7,7-苯并降冰片二烯系统。2）在效率较低的二氢苯并barrelene系统中，取代基对效率的影响更为明显。3）如果取代基的自由基稳定作用较大，则效率较高。但是，取代基提高体系间穿越至起始材料基态的速率的作用降低了效率。4）通过取代基的自由基稳定作用控制区域选择性。5）在双取代系统中，第二个取代基有助于提高效率。