1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)- | 15914-95-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)-
• 英文别名: exo-endo-tetracyclo<6.2.1.1^3,6.0^2,7>dodecane；1,2,3,4,4a,5,6,7,8,8a-decahydro-1,4-exo,endo-5,8-dimethanonaphthalene；exo,endo-perhydro-1,4:5,8-dimethanonaphthalene；(4ac,8ac)-decahydro-1r,4;5t,8-dimethano-naphthalene；(4ac,8ac)-Decahydro-1r,4;5t,8-dimethano-naphthalin；(4arH.8acH)-Decahydro-1c.4c:5t.8t-dimethano-naphthalin；exo,endo-Tetracyclo<6.2.1.0^2,7.1^3,6>dodecan
• CAS: 15914-95-1
• 化学式: C₁₂H₁₈
• 分子量: 162.275
• InChiKey: VSHDEZHNJCSDFY-CJXDBHJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)- 在 ruthenium trichloride 、 sodium periodate 、 水 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 144.0h， 以35%的产率得到anti-tricyclo<6.2.1.^1,81^3,6>dodecane-2,7-dione
  参考文献：
  名称：

  钌催化的CH键活化。环状饱和烃氧官能化协同机理的证据

  摘要：

  用原位生成的RuO 4氧化桥连的多环烷烃是通过一种协同机制进行的，该机制涉及高度亲电的氧钌物种与叔无障碍C–H键的相互作用。

  DOI：

  10.1039/c39900001344
• 作为产物：
  描述：

  aldrin 在 palladium on activated charcoal lithium 、 氢气 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)-
  参考文献：
  名称：

  Steric effects on carbon-13 NMR shifts: carbon-hydrogen bond polarization contributions

  摘要：

  The shielding observed in the chemical shifts of carbon atoms subjected to steric compression was originally attributed to carbon-hydrogen bond polarization. There is increasing evidence that this is not universally the case and theoretical studies reveal that changes in dihedral angles may be responsible for many steric effects. Hydrogen shifts, bond lengths and charge distributions were used as probes for these effects in methylnorbornanes and similar tetracyclic norbornyl hydrocarbons. Carbon-hydrogen bond polarization can make a significant contribution to shielding and can be distinguished from effects caused by changes in dihedral angles due to steric congestion. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1097-458x(199804)36:4<261::aid-omr261>3.0.co;2-1

文献信息

• The unexpected regio- and stereo-specific Diels–Alder reaction between cyclopentadiene and 2-benzenesulphonyl-3-trimethylsilylbicyclo[2.2.1]hepta-2,5-diene
  作者：Richard Vaughan Williams、Chiu-Lien Ann Sung

  DOI：10.1039/c39870000590

  日期：——

  The title reaction exhibits remarkable specificity as only one of the eight possible regio- and stereo-isomers is obtained in 98% yield; the structure of this single adduct is elucidated by chemical degradation.

  标题反应显示出显着的特异性，因为仅以98％的产率获得了8种可能的区域和立体异构体之一。这种单一加合物的结构可通过化学降解来阐明。
• Lucchi, Ottorino De; Piccolrovazzi, Nicoletta; Licini, Giulia, Gazzetta Chimica Italiana, 1987, vol. 117, # 7, p. 401 - 408
  作者：Lucchi, Ottorino De、Piccolrovazzi, Nicoletta、Licini, Giulia、Modena, Giorgio、Valle, Giovanni

  DOI：——

  日期：——
• Hydrogenation on the hindered face of syn-sesquinorbornene photosensitized by acetone
  作者：Paul D. Bartlett、Antonius A. M. Roof、William J. Winter

  DOI：10.1021/ja00411a053

  日期：1981.10
• Electronic control of stereoselectivity. 4. Effects of neighboring fused bicyclic frameworks on the stereochemical outcome of Diels-Alder cycloadditions to cyclopentadiene rings
  作者：Michael C. Boehm、Richard V. C. Carr、Rolf Gleiter、Leo A. Paquette

  DOI：10.1021/ja00544a008

  日期：1980.11
• Electronic control of stereoselectivity. 3. Stereoselection operative in [4 + 2].pi. cycloadditions to cyclopentadiene rings fused at C2,C3 to bicyclic frameworks
  作者：Leo A. Paquette、Richard V. C. Carr、Michael C. Boehm、Rolf Gleiter

  DOI：10.1021/ja00523a058

  日期：1980.1