(Z,Z)-1,5-cyclododecadiene | 31821-17-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (Z,Z)-1,5-cyclododecadiene
• 英文别名: 1,5-cyclododecadiene；Cyclododecadien-(1c,5c)；(1Z,5Z)-cyclododeca-1,5-diene
• CAS: 31821-17-7
• 化学式: C₁₂H₂₀
• 分子量: 164.291
• InChiKey: KEMUGHMYINTXKW-NQOXHWNZSA-N

物化性质

• 保留指数：
  1354;1364;1372

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为产物：
  描述：

  dodeca-2,10-diyne-1,12-diol 在 Lindlar's catalyst 四丁基高氯酸铵 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (Z,Z)-1,5-cyclododecadiene
  参考文献：
  名称：

  Synthesis of (E,E)- and (Z,Z)-1,5-Cycloalkadienes by Means of the Electrochemical Cyclization of Allylic 1,ω-Dibromides

  摘要：

  四氢呋喃中（E,E）-1,n-二溴-2,（n-2）-烯二炔（n=12, 14）的电解反应生成了相应的十二或十四元（E,E）-1,5-环烯二炔，尽管产率较低，同时伴随着（E）-4-乙烯基环烯和异构烯二炔的生成。类似地，（Z,Z）-1,n-二溴-2,（n-2）-烯二炔（n=10, 12, 14）的电解反应生成了相应的十、十二或十四元（Z,Z）-1,5-环烯二炔，产率为11%至13%，同时伴随着（Z）-4-乙烯基环烯和异构烯二炔的形成。

  DOI：

  10.1246/bcsj.60.2429

文献信息

• Studies on partial hydrogenation of 1,5,9-cyclo-dodecatriene towards cyclo-dodecene
  作者：J. Gaube、W. David、R. Sanchayan、N. Wuchter、H.-F. Klein

  DOI：10.1016/j.apcata.2011.09.003

  日期：2011.12

  The selective hydrogenation of 1,5,9-cis,trans,trans-cyclo-dodecatriene (1,5,9-ctt-CDT) towards cyclododecene (CDE) depends strongly on the pressure of hydrogen, respectively the hydrogenation rate. High yields of CDE (>90%) can only be reached at extremely low hydrogen pressure. In order to elucidate this exceptional reaction performance the course of reaction has been studied for a wide range of hydrogen pressure, 0.01 > P-H2 > 2.5 MPa, taking into consideration data of other research groups. The CDT hydrogenations were discontinuously carried out in liquid phase on Pd/Al2O3 at T = 353 K.The resulting hypothesis of this study is that the very low reaction rate at low p(H2) is necessary in order to realize a dense surface coverage of 1,5,9-CDT and 1,5-cyclo-dodecadiene (CDD) isomers where these molecules show adsorption on Pd via two double bonds so that readsorption of formed CDE and subsequent hydrogenation to cyclo-dodecane (CDA) is hardly possible.On the whole this new hypothesis on the reaction course of CDT hydrogenation gives a sound and fully consistent view on this rather complicated reaction. (C) 2011 Elsevier B.V. All rights reserved.
• TOKUDA, MASAO;SATOH, KUNIAKI;SUGINOME, HIROSHI, BULL. CHEM. SOC. JAP., 60,(1987) N 7, 2429-2433
  作者：TOKUDA, MASAO、SATOH, KUNIAKI、SUGINOME, HIROSHI

  DOI：——

  日期：——
• Synthesis of (<i>E</i>,<i>E</i>)- and (<i>Z</i>,<i>Z</i>)-1,5-Cycloalkadienes by Means of the Electrochemical Cyclization of Allylic 1,ω-Dibromides
  作者：Masao Tokuda、Kuniaki Satoh、Hiroshi Suginome

  DOI：10.1246/bcsj.60.2429

  日期：1987.7

  Electrolysis of (E,E)-1,n-dibromo-2,(n-2)-alkadienes (n=12, 14) in tetrahydrofuran gave the corresponding twelve or fourteen-membered (E,E)-1,5-cycloalkadienes, albeit in low yields, together with (E)-4-vinylcycloalkenes and isomeric alkadienes. Similar electrolysis of (Z,Z)-1,n-dibromo-2,(n-2)-alkadienes (n=10, 12, 14) gave the corresponding ten, twelve, or fourteen-membered (Z,Z)-1,5-cycloalkadienes in 11 to 13% yields, with the accompanying formation of (Z)-4-vinylcycloalkenes and isomeric alkadienes.

  四氢呋喃中（E,E）-1,n-二溴-2,（n-2）-烯二炔（n=12, 14）的电解反应生成了相应的十二或十四元（E,E）-1,5-环烯二炔，尽管产率较低，同时伴随着（E）-4-乙烯基环烯和异构烯二炔的生成。类似地，（Z,Z）-1,n-二溴-2,（n-2）-烯二炔（n=10, 12, 14）的电解反应生成了相应的十、十二或十四元（Z,Z）-1,5-环烯二炔，产率为11%至13%，同时伴随着（Z）-4-乙烯基环烯和异构烯二炔的形成。

表征谱图