dimethyl 13-anti,18-anti-dibromononacyclo<12.6.0.0^2,6.0^4,11.0^5,9.0^7,20.0^10,17.0^12,16.0^15,19>icosa-1(20),10-diene-3-syn,8-syn-dicarboxylate | 124316-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 13-anti,18-anti-dibromononacyclo<12.6.0.0^2,6.0^4,11.0^5,9.0^7,20.0^10,17.0^12,16.0^15,19>icosa-1(20),10-diene-3-syn,8-syn-dicarboxylate
• CAS: 124316-56-9
• 化学式: C₂₄H₂₂Br₂O₄
• 分子量: 534.244
• InChiKey: CTAOOVNGACMGJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  蒽 、 dimethyl 13-anti,18-anti-dibromononacyclo<12.6.0.0^2,6.0^4,11.0^5,9.0^7,20.0^10,17.0^12,16.0^15,19>icosa-1(20),10-diene-3-syn,8-syn-dicarboxylate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 8,9;27,28;29,30;31,32-tetrabenzopentadecacyclo[24.2.2.2^7,10.0^2,22.0^2,25.0^3,14.0^4,21.0^5,13.0^6,11.0^6,20.0^11,18.0^12,16.0^15,25.0^17,24.0^19,23]dotriacontane-4,16-dicarboxylic acid
  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

文献信息

• From Pagodanes to Dodecahedranes - Search for a Serviceable Access to the Parent (C 20 H 20 ) Hydrocarbon ** **Dedicated to Professor W. von E. Doering on the occasion of his 80th birthday. H.P. very fondly remembers his two post-doc years at Yale University (1957–59).
  作者：Martin Bertau、Fabian Wahl、Andreas Weiler、Klaus Scheumann、Jürgen Wörth、Manfred Keller、Horst Prinzbach

  DOI：10.1016/s0040-4020(97)00345-1

  日期：1997.7

  novel SN2 pagodane → dodecahedrane routes a preparatively potent access to the parent pentagonal dodecahedrane (2) was explored. The one-pot catalytic procedure (Pd/C/H2) starting from an eightfold functionalized secopagodane (14, C20H12Br6 (CO2 CH3)2) excells in shortness but, rather erratic (33–53%), falls out of the competition. The longer route via 1,6-dicarboxyl/dibromo dodecahedranes (35, 22)

  通过利用新颖的S N 2 pagodane→十二面体路线，探索了对母体五边形十二面体的有效制备途径（2）。一锅催化程序（Pd / C / H 2）从八倍官能化的二十二碳五烷（14，C 20 H 12 Br 6（CO 2 CH 3）2）开始，但在短时间内却表现不佳，但不稳定（33-53％） ，从竞争中脱颖而出。经由较长的路线1,6-二羧基/二溴dodecahedranes（35，22原来作为首选与基于公共pagodane前体的74-76％的总产率）（13）。©1997爱思唯尔科学有限公司。