dodecahedranol | 112896-36-3

• 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: dodecahedranol
• 英文别名: Undecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]icosan-1-ol
• CAS: 112896-36-3
• 化学式: C₂₀H₂₀O
• 分子量: 276.378
• InChiKey: PWRHSMLABYNSSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dodecahedranol 生成 1,2-dibromoundecacyclo[9.9.0.0^2,9.0^3,7.0^4,20.0^5,18.0^6,16.0^8,15.0^10,14.0^12,19.0^13,17]icosane
  参考文献：
  名称：

  OLAH, GEORGE A.;PRAKASH, G. K. SURYA;KOBAYASHI, TOMOSHIGE;PAQUETTE, LEO A+, J. AMER. CHEM. SOC., 110,(1988) N 4, 1304-1305

  摘要：

  DOI：
• 作为产物：
  描述：

  (trifluoroacethoxy)dodecahedrane 在 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 dodecahedranol
  参考文献：
  名称：

  Dodecahedrane. Improved synthetic access to, and monofunctionalization of, the spherical hydrocarbon. Spectral properties of the derivatives

  摘要：

  DOI：

  10.1021/ja00234a003

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。
• Chemical properties of dodecahedrane. Monofunctionalization reactions
  作者：Leo A. Paquette、Jeffrey C. Weber、Tomoshige. Kobayashi

  DOI：10.1021/ja00212a055

  日期：1988.2
• The dodecahedryl radical. Reactivity analysis by conjugate addition to .pi.-electron-deficient acceptors and structural investigation by electron spin resonance spectroscopy
  作者：Leo A. Paquette、Dean R. Lagerwall、Hans Gert Korth

  DOI：10.1021/jo00046a024

  日期：1992.9

  The bromo and phenylseleno derivatives of dodecahedrane have been identified as suitable precursors to the dodecahedryl radical (4). This reactive intermediate exhibits only modest reactivity, lending itself to capture by the most powerful radical traps, which include acrylonitrile, 2-cyclopentenone, and allyltri-n-butylstannane. ESR studies performed on the same two starting materials have provided additional striking evidence that 4 and its closest model, the 1-adamantyl radical, differ widely in their properties. Reaction conditions that result in smooth generation of the adamantyl species did not lead to ESR spectra that can be related to 4.
• Electrophilic chemistry of dodecahedrane. Direct entry to epoxydodecahedrane and the first tethered derivative
  作者：Leo A. Paquette、Dean R. Lagerwall、John L. King、Satomi Niwayama、Renato Skerlj

  DOI：10.1016/s0040-4039(00)92358-x

  日期：1991.9

  (Phenylseleno)dodecahedrane is shown to be a useful precursor of dodecahedrene (not isolated) and epoxydodecahedrane. The conjoining of two dodecahedryl units in a para relationship on a benzene ring has also been realized.
• PAQUETTE, LEO A.;WEBER, JEFFREY C.;KOBAYASHI, TOMOSHIGE;MIYAHARA, YUJI, J. AMER. CHEM. SOC., 110,(1988) N6, C. 8591-8599
  作者：PAQUETTE, LEO A.、WEBER, JEFFREY C.、KOBAYASHI, TOMOSHIGE、MIYAHARA, YUJI

  DOI：——

  日期：——