allyldodecahedrane | 138826-14-9

• 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: allyldodecahedrane
• 英文别名: 1-Prop-2-enylundecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]icosane
• CAS: 138826-14-9
• 化学式: C₂₃H₂₄
• 分子量: 300.444
• InChiKey: QUZXCQHUXLDRGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  allyldodecahedrane 在 吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以63%的产率得到dodecahedrylacetaldehyde
  参考文献：
  名称：

  The dodecahedryl radical. Reactivity analysis by conjugate addition to .pi.-electron-deficient acceptors and structural investigation by electron spin resonance spectroscopy

  摘要：

  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.

  DOI：

  10.1021/jo00046a024
• 作为产物：
  描述：

  bromododecahedrane 、 烯丙基三甲基硅烷 在 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以65%的产率得到allyldodecahedrane
  参考文献：
  名称：

  The dodecahedryl radical. Reactivity analysis by conjugate addition to .pi.-electron-deficient acceptors and structural investigation by electron spin resonance spectroscopy

  摘要：

  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.

  DOI：

  10.1021/jo00046a024

文献信息

• The dodecahedryl anion
  作者：Leo A. Paquette、Dean R. Lagerwall、John L. King、Satomi Niwayama

  DOI：10.1016/0040-4039(91)80211-n

  日期：1991.11

  The feasibility of generating the anion of dodecahedrane by direct metalation, by reductive lithiation with aromatic radical anions, and by transmetalation with alkyllithiums has been examined.
• 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.