dodecahedrene | 77159-24-1

• 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: dodecahedrene
• 英文别名: Dodecahedrene；Undecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]icos-1-ene；undecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]icos-1-ene
• CAS: 77159-24-1
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: FWBDDUUQSGLEQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  蒽 、 dodecahedrene 以 苯 为溶剂， 反应 1.0h， 以93%的产率得到23,24;25,26-dibenzo-tridecacyclo[20.2.2.0^2,6.0^2,21.0^3,13.0^4,11.0^5,9.0^7,20.0^8,18.0^10,17.0^12,16.0^14,21.0^15.19]hexacosane
  参考文献：
  名称：

  Unsaturated Dodecahedranes—In Quest of the C20H14 1,4,16-Triene and C20H12 1,4,10(14),16-Tetraene, and Their Cations and Anions

  摘要：

  The highly pyramidal, highly strained 1,4,16-dodecahedratriene (4) and C20H12 1,4,10(14),16-dodecahedratetraene (5) are cage olefins with an intriguing "inner life". For 5 DFT calculations give information about the energetic and geometrical consequences of one-/two-electron oxidation and reduction. Attempts to prepare 4 and 5 through thermal retro[2+2]/[4+2]cycloaddition strategies proved unsuccessful. Still, the C20H14/C20H12 cage cations and anions are liberated upon electron impact or gas-discharge ionization of their thermally extremely stable tris-/tetrakisanthraceno-anellated derivatives. Mass-selection (photoelectron (PE) characterization) of the anions failed, however, due to the very small anion intensity, the preferential formation of hydrogen-poor ions, and minor cage disruption.

  DOI：

  10.1002/1521-3765(20020118)8:2<509::aid-chem509>3.0.co;2-d
• 作为产物：
  描述：

  C₂₀H₁₉N 在 吡啶 、 nitrosonium tetrafluoroborate 作用下， 生成 dodecahedrene
  参考文献：
  名称：

  通往十二面体的不饱和十二面体的帕戈丹路线，保护和脱保护

  摘要：

  由适当官能化的bisseco底物制备单不饱和，高锥体化，高反应性（亲双亲，亲双极性）的十二面体（2，10）。在制备十二面体多烯中，潜在的方法学是探亲性（-N 2 O； -SO 2）和逆向DA反应。

  DOI：

  10.1016/s0040-4039(00)92326-8

文献信息

• Bromination of Unsaturated Dodecahedranes—En Route to C20 Fullerene
  作者：Emmerich Sackers、Thomas Oßwald、Klaus Weber、Manfred Keller、Dieter Hunkler、Jürgen Wörth、Lothar Knothe、Horst Prinzbach

  DOI：10.1002/chem.200501609

  日期：2006.8.16

  generally in polyunsaturated dodecahedranes (in the extreme C(20)H(4), "tetrahydro-C(20) fullerenes"). Only subsequently did skeletal fragmentations occur. From X-ray crystal-structure analyses, more information was obtained on the structural response of the dodecahedral skeleton to the strain induced by the voluminous substituents. As Appendix, the forcing radical bromination of 1,6-dibromododecahedrane

  作为实现十二面体C（20）骨架的选择性低聚（多溴化）或最终全溴化的研究的一部分，研究了十二碳烯和1,16-十二碳二烯的离子溴化的程度和方向。沿着Br（+）加/去质子和烯丙基重排的顺序，最多可取代10个氢原子（C（20）H（x）Br（10）的痕迹）。在限定的条件下以高达50％的总收率得到四溴十二碳烯，其中三个和四个烯丙基溴取代基保护极度弯曲的C == C键，甚至对氧也无反应性，但与CH（2）N（2）迅速反应。新固定的低聚（poly）bromododecahedra（e）nes的电子碰撞电离（MS）后，取代基的顺序丢失通常以多不饱和十二面体为代表（在极端C（20）H（4）中，
• Unsaturated Dodecahedranes—In Quest of the C20H14 1,4,16-Triene and C20H12 1,4,10(14),16-Tetraene, and Their Cations and Anions
  作者：Jens Reinbold、Emmerich Sackers、Thomas Oßwald、Klaus Weber、Andreas Weiler、Torsten Voss、Dieter Hunkler、Jürgen Wörth、Lothar Knothe、Frank Sommer、Nina Morgner、Bernd von Issendorff、Horst Prinzbach

  DOI：10.1002/1521-3765(20020118)8:2<509::aid-chem509>3.0.co;2-d

  日期：2002.1.18

  The highly pyramidal, highly strained 1,4,16-dodecahedratriene (4) and C20H12 1,4,10(14),16-dodecahedratetraene (5) are cage olefins with an intriguing "inner life". For 5 DFT calculations give information about the energetic and geometrical consequences of one-/two-electron oxidation and reduction. Attempts to prepare 4 and 5 through thermal retro[2+2]/[4+2]cycloaddition strategies proved unsuccessful. Still, the C20H14/C20H12 cage cations and anions are liberated upon electron impact or gas-discharge ionization of their thermally extremely stable tris-/tetrakisanthraceno-anellated derivatives. Mass-selection (photoelectron (PE) characterization) of the anions failed, however, due to the very small anion intensity, the preferential formation of hydrogen-poor ions, and minor cage disruption.
• The pagodane route to dodecahedranes-unsaturated dodecahedranes, protection and deprotection
  作者：Klaus Weber、Hans Fritz、Horst Prinzbach

  DOI：10.1016/s0040-4039(00)92326-8

  日期：1992.1

  Monounsaturated, highly pyramidalized, highly reactive (i.a. dienophilic, dipolarophilic) dodecahedranes (2,10) are prepared from an adequately functionalized bisseco substrate. Cheletropic (-N2O; -SO2) and retro-DA reactions are probed as potential methodologies in the preparation of dodecahedrapolyenes.

  由适当官能化的bisseco底物制备单不饱和，高锥体化，高反应性（亲双亲，亲双极性）的十二面体（2，10）。在制备十二面体多烯中，潜在的方法学是探亲性（-N 2 O； -SO 2）和逆向DA反应。