isopropylideneadamantane oxide | 156639-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: isopropylideneadamantane oxide
• 英文别名: 3',3'-Dimethylspiro[adamantane-2,2'-oxirane]
• CAS: 156639-58-6
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: NGXYFEMWIQTZNR-UHFFFAOYSA-N

物化性质

• 沸点：
  249.4±8.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isopropylideneadamantane oxide 在 甲基(三氟甲基)-1,3-二环氧丙烷 、 高碘酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-羟基-2-金刚烷酮
  参考文献：
  名称：

  Chemo- and regioselective oxidation of adamantyl derivatives by dioxiranes

  摘要：

  Methyl(trifluoromethyl) dioxirane (1) gives direct chemo- and regioselective oxidation of methyleneadamantane oxide (2) and isopropylideneadamantane oxide (3) in high yield under mild conditions. Secondary C H are not appreciably oxidized and high regioselectivities were observed for attack at tertiary C-H. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00876-6
• 作为产物：
  描述：

  2-isopropylideneadamantane 在 Fe(AAEMA)3 、 氧气 、 异丁醛 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 isopropylideneadamantane oxide
  参考文献：
  名称：

  铁（III）的可聚合β-酮酸酯配合物催化受阻烯烃和烯醇醚的好氧环氧化

  摘要：

  在Mukaiyama的条件下，已使用铁（III）催化中心将特殊的受阻烯烃和衍生物进行了环氧化。实验结果可以排除单重态氧和游离过氧酸作为活性物质的参与。

  DOI：

  10.1016/s0040-4039(00)73259-x

文献信息

• Aerobic epoxidation of hindered olefins and enol ethers catalyzed by a polymerizable β-ketoesterate complex of iron(III)
  作者：Luigi Lopez、Piero Mastrorilli、Giuseppe Mele、Cosimo F. Nobile

  DOI：10.1016/s0040-4039(00)73259-x

  日期：1994.5

  Peculiar hindered olefins and derivatives have been epoxidized, under Mukaiyama's conditions, using iron(III) catalytic centres. The experimental results allow to rule out the involvement of singlet oxygen and free peroxyacids as active species.

  在Mukaiyama的条件下，已使用铁（III）催化中心将特殊的受阻烯烃和衍生物进行了环氧化。实验结果可以排除单重态氧和游离过氧酸作为活性物质的参与。
• Lopez Luigi, Mastrorilli Piero, Mele Giuseppe, Nobile Cosimo F., Tetrahedron Lett, 35 (1994) N 21, S 3633-3636
  作者：Lopez Luigi, Mastrorilli Piero, Mele Giuseppe, Nobile Cosimo F.

  DOI：——

  日期：——
• Aerobic oxidations of unsaturated substrates under mukaiyama's conditions: The role of the metal and of the sacrificial aldehyde
  作者：Piero Mastrorilli、Cosimo F. Nobile、Gian P. Suranna、Luigi Lopez

  DOI：10.1016/0040-4020(95)00410-a

  日期：1995.7

  Aerobic epoxidation of unsaturated substrates has been achieved under Mukaiyama's conditions (atmospheric pressure of dioxygen, in the presence of an excess of sacrificial aldehyde) with or without metal catalyst. The influence of light in non-catalysed reactions and the possible role of the aldehyde and of the metal complex in catalysed reactions are discussed. Two mechanistic pathways are proposed for Co(II) and Fe(III) [Ni(II)] catalytic centres.
• Chemo- and regioselective oxidation of adamantyl derivatives by dioxiranes
  作者：Lucia D'Accolti、Ping Kang、Saeed Khan、Ruggero Curci、Christopher S. Foote

  DOI：10.1016/s0040-4039(02)00876-6

  日期：2002.5

  Methyl(trifluoromethyl) dioxirane (1) gives direct chemo- and regioselective oxidation of methyleneadamantane oxide (2) and isopropylideneadamantane oxide (3) in high yield under mild conditions. Secondary C H are not appreciably oxidized and high regioselectivities were observed for attack at tertiary C-H. (C) 2002 Elsevier Science Ltd. All rights reserved.