(+/-)-Benzobicyclo<2.2.1>heptan-2-one | 7374-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-Benzobicyclo<2.2.1>heptan-2-one
• 英文别名: (+/-)-2-benzonorbornenone；Benzonorbornene-2-one；2-benzonorbornenone；2-Keto-benzo-bicyclo<2,2,1>hepten；Benzonorbonenon；(+/-)-Benzobicyclo[2.2.1]heptan-2-one；(1S,8S)-tricyclo[6.2.1.02,7]undeca-2,4,6-trien-9-one
• CAS: 7374-90-5；21159-73-9；35001-30-0；74958-42-2
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: MMDLBADSUSAPKF-XVKPBYJWSA-N

物化性质

• 沸点：
  286.5±29.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (+/-)-Benzobicyclo<2.2.1>heptan-2-one 在 L-Selectride 作用下， 以95%的产率得到(+/-)-endo-2-benzonorbornenol
  参考文献：
  名称：

  A convenient route to both enantiomers of endo-2-benzonorbornenol via lipase catalysed resolution of the racemic mixture

  摘要：

  Resolution of racemic endo-benzonorbornenol (+/-)-4 was performed using Candida antaretica lipase (Novozym" 435) in benzene (50 degreesC;50 hours) with vinyl acetate as the acyl donor to afford (-)-endo-2-benzonorbornenol (-)-6 and their corresponding (+)-endo-2-benzonorbornenyl acetate (+)-5 in high e.e.s of up to 99'% and workable yields of up to 45-46%. (C) 2001 Elsevier Science Ltd. All rights: reserved.

  DOI：

  10.1016/s0957-4166(01)00079-9
• 作为产物：
  描述：

  (+/-)-exo-2-benzonorbornenol 在 吡啶 、 chromium(VI) oxide 作用下， 以80%的产率得到(+/-)-Benzobicyclo<2.2.1>heptan-2-one
  参考文献：
  名称：

  A convenient route to both enantiomers of endo-2-benzonorbornenol via lipase catalysed resolution of the racemic mixture

  摘要：

  Resolution of racemic endo-benzonorbornenol (+/-)-4 was performed using Candida antaretica lipase (Novozym" 435) in benzene (50 degreesC;50 hours) with vinyl acetate as the acyl donor to afford (-)-endo-2-benzonorbornenol (-)-6 and their corresponding (+)-endo-2-benzonorbornenyl acetate (+)-5 in high e.e.s of up to 99'% and workable yields of up to 45-46%. (C) 2001 Elsevier Science Ltd. All rights: reserved.

  DOI：

  10.1016/s0957-4166(01)00079-9

文献信息

• Sympathomimetic effects of <i>exo-</i> and <i>endo-</i> isomers of 2-aminobenzonorbornene in vitro and in vivo
  作者：P Burn、P A Crooks、B L Ratcliffe、J M H Rees

  DOI：10.1111/j.2042-7158.1980.tb12858.x

  日期：2011.4.12

  A stereospecific synthesis of endo-2-aminobenzornorbornene is described. Its sympathomimetic activities and those of its N-methyl derivative were compared with the equivalent exo- isomers using the isolated rat anococcygeus muscle and the anaesthetized rat blood pressure preparations. On the anococcygeus muscle preparation the endo- and exo-isomers of the primary amines had similar indirectly acting sympathomimetic activities. In contrast the exo-N-methyl derivative was a far more potent sympathometic in vitro than the endo-N methyl isomer. In the anaesthetized rat the exo- and endo-isomers of 2-aminobenzonorbornene and their N-methyl derivatives all had similar pressor activities, though the successive injections of the two exo-derivatives suggested an additional α-adrenoceptor blocking activity. The actions of these rigid sympathomimetics are compared with those of the flexible amphetamine structure.

  标题：摘要 本文描述了一种内向型2-氨基苯并莫尔芬的立体特异性合成方法。通过使用孤立的大鼠肛门尾肌和麻醉大鼠血压制备物来比较其类交感活性及其N-甲基衍生物与相应的外向型异构体的类交感活性。在肛门尾肌制备物中，原始胺的内向型和外向型异构体具有类似的间接作用的类交感活性。相比之下，外向型N-甲基衍生物在体外比内向型N-甲基异构体具有更强的类交感作用。在麻醉大鼠中，2-氨基苯并莫尔芬的内向型和外向型异构体及其N-甲基衍生物的升压活性相似，尽管两个外向型衍生物的连续注射表明它们具有额外的α-肾上腺素能受体阻滞活性。这些刚性类交感剂的作用与柔性的安非他命结构进行了比较。
• Organic photochemistry. 40. Photochemistry of bichromophoric molecules. Photochemistry and photophysics of 2-methylenebenzonorbornene and related nonconjugated aryl olefins in nonprotic media
  作者：Frank Scully、Tom Nylund、Fred Palensky、Harry Morrison

  DOI：10.1021/ja00491a037

  日期：1978.11
• Ipaktschi,J., Chemische Berichte, 1972, vol. 105, p. 1840 - 1853
  作者：Ipaktschi,J.

  DOI：——

  日期：——
• Microbial stereodifferentiating reduction of carbonyl compounds; proposed quadrant rule
  作者：Masao Nakazaki、Hiroaki Chikamatsu、Koichiro Naemura、Masaaki Asao

  DOI：10.1021/jo01310a033

  日期：1980.10
• Evidence for anti-bond migration in the photorearrangement of 2-D-exo-benzonorbornenyl-2-chloride
  作者：Harry Morrison、Lourdes M. De Cárdenas

  DOI：10.1016/s0040-4039(01)81222-3

  日期：1984.1