endo-trans-exo-pentacyclo<8.2.1.14,7.02,9.03,8>tetradecane-5,11-diene | 2957-68-8

• 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: endo-trans-exo-pentacyclo<8.2.1.14,7.02,9.03,8>tetradecane-5,11-diene
• 英文别名: endo-trans-exo-pentacyclo<8.2.1.1^4,7.0^2,9.0^3,8>tetradecane-5,11-diene；endo,trans,exo-pentacyclo[8.2.1.1^4,7.0^2,9.0^3,8]tetradeca-5,11-diene；endo-trans-exo-pentacyclo[8.2.1.1^4,7.0^2,9.0^3,8]tetradecane-5,11-diene
• CAS: 2957-68-8
• 化学式: C₁₄H₁₆
• 分子量: 184.281
• InChiKey: KPBWFFSGJYAHSX-QLOYHPGWSA-N

物化性质

• 沸点：
  268.5±40.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  endo-trans-exo-pentacyclo<8.2.1.14,7.02,9.03,8>tetradecane-5,11-diene 在 氢气 作用下， 生成 endo-trans-exo-pentacyclo[8.2.1.14,7.02,9.03,8]tetradecane
  参考文献：
  名称：

  13C NMR spectra of polycyclic compounds and the stereochemistry of norbornadiene dimers and trimers

  摘要：

  DOI：

  10.1007/bf00948838
• 作为产物：
  描述：

  2,5-降冰片二烯 在 双三苯基膦二羰基镍 作用下， 生成 endo-trans-exo-pentacyclo<8.2.1.14,7.02,9.03,8>tetradecane-5,11-diene
  参考文献：
  名称：

  Trimeric structure and mixed cycloaddition from the nickel-catalyzed reaction of norbornadiene

  摘要：

  DOI：

  10.1021/jo00890a027

文献信息

• Catalytic syntheses of polycyclic compounds based on norbornadiene in the presence of nickel catalysts
  作者：I. E. Efros、D. V. Dmitriev、V. R. Flid

  DOI：10.1134/s0023158410030079

  日期：2010.6

  The cycloadditions of olefins containing an electron-withdrawing substituent to norbornadiene are reported. The influence of the substituent and solvent nature on the [2+2+ 2]-cycloadduct yield and stereoselectivity is elucidated. The competitive cycloaddition of pairs of olefins to norbornadiene is discussed. Hypotheses about the structure of key intermediates of the process are considered. The consistent generalized mechanism for the cycloaddition of unsaturated compounds of various classes to norbornadiene is suggested.
• The ferric chloride-catalyzed Ritter amidation of norbornane-type dienes
  作者：Ravil I. Khusnutdinov、Tatyana M. Egorova、Ekaterina S. Meshcheryakova、Leonard M. Khalilov、Usein M. Dzhemilev

  DOI：10.1016/j.mencom.2019.03.007

  日期：2019.3

  The FeCl3 center dot 6H(2)O catalyzed Ritter amidation of norbornane dienes with aceto- and propionitriles in the presence of water (145 degrees C, 6 h) affords the corresponding amides in yields of 35-87%.
• Synthesis of new types of strained hydrocarbons by cyclo-codimerization of quadricyclane with norbornenes and their derivatives, catalyzed by palladium complexes
  作者：U. M. Dzhemilev、R. I. Khusnutdinov、V. A. Dokichev、D. K. Galeev、A. I. Malikov、G. A. Tolstikov、O. M. Nefedov

  DOI：10.1007/bf00961046

  日期：1991.11

  The codimerization of quadricyclane (QC), the valence isomer of norbornadiene (NBD), with norbornene compounds was studied in the presence of Pd(0) complexes. Codimerization of QC with norbornene, 5-methyl- and 5-methylenenorbornene, exo-tricyclo[3.2.1.0(2,4)]octene-6, tetracyclo[4.2.0.0(2,4).0(3,7)]nonene-8, and penta- and hexacyclic NBD dimers was carried out in the presence of PPh3-activated Pd2(DBA)3.CHCl3 to afford a new class of hexa- to nonacyclic strained hydrocarbons with exo- and endo-tetracyclo[4.2.0.0(2,4).0(3,7)]nonane fragments.
• Stereoselective exo-addition to norbornenes of acetic acid generated from vinyl acetate in the presence of rhodium complexes
  作者：R. I. Khusnutdinov、N. A. Shchadneva、L. F. Mukhametshina

  DOI：10.1134/s1070428010010045

  日期：2010.1

  Rhodium complexes catalyzed decomposition of vinyl acetate with liberation of acetic acid and subsequent stereoselective exo-addition of the latter to norbornene and its derivatives under mild conditions.
• Nickel complex-catalyzed codimerization of allyl esters with compounds in the norbornene series
  作者：U. M. Dzhemilev、R. I. Khusnutdinov、D. K. Galeev、O. M. Nefedov、G. A. Tolstikov

  DOI：10.1007/bf00953861

  日期：1987.1