2-tert-Cumyl-2-adamantanol | 110808-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-tert-Cumyl-2-adamantanol
• 英文别名: 2-Cumyl-2-adamantanol；2-cumyladamantan-2-ol；2-(2-Phenylpropan-2-yl)adamantan-2-ol
• CAS: 110808-54-3
• 化学式: C₁₉H₂₆O
• 分子量: 270.415
• InChiKey: VUCAANIRQHCHCD-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  384.3±11.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  2-tert-Cumyl-2-adamantanol 在 三乙基硅烷 、 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到2-Cumyladamantane
  参考文献：
  名称：

  Unstable compounds. Synthesis, structure, and experimental and computational carbocation chemistry of 2-cumyladamantan-2-ol and its chromium .eta.6-Cr(CO)3 complex

  摘要：

  Structures of the title alcohol (1) and its chromium tricarbonyl complex (1a), were determined by single-crystal X-ray diffraction methods and were found to be very similar. Both of the alcohols were subjected to treatment with strong acids, and the behavior of the resulting carbocations was studied. Little difference between the two systems was noted. Both gave a mixture of predominantly phenyl- and methyl-shifted olefinic and cyclopropane dehydration products under various reaction conditions. These presumably arose from the corresponding rearranged cations. H-1 and C-13 NMR spectra of the cation derived from the title alcohol were obtained under stable ion conditions. Trapping of this species by triethylsilane at -78-degrees-C produced a 96% yield of 2-cumyladamantane. Semiempirical molecular orbital calculations (MNDO, AM1, and PM3) of the energies of the optimized structures of reactants, presumed intermediates, and products of the reactions, together with estimates of the energy barriers for the minimum energy reaction pathways, were used to understand the nature of the reaction mechanism.

  DOI：

  10.1021/jo00015a023
• 作为产物：
  描述：

  金刚烷酮 、 ALFA, ALFA-二甲基苄氯 在 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到2-tert-Cumyl-2-adamantanol
  参考文献：
  名称：

  Unstable compounds. Synthesis, structure, and experimental and computational carbocation chemistry of 2-cumyladamantan-2-ol and its chromium .eta.6-Cr(CO)3 complex

  摘要：

  Structures of the title alcohol (1) and its chromium tricarbonyl complex (1a), were determined by single-crystal X-ray diffraction methods and were found to be very similar. Both of the alcohols were subjected to treatment with strong acids, and the behavior of the resulting carbocations was studied. Little difference between the two systems was noted. Both gave a mixture of predominantly phenyl- and methyl-shifted olefinic and cyclopropane dehydration products under various reaction conditions. These presumably arose from the corresponding rearranged cations. H-1 and C-13 NMR spectra of the cation derived from the title alcohol were obtained under stable ion conditions. Trapping of this species by triethylsilane at -78-degrees-C produced a 96% yield of 2-cumyladamantane. Semiempirical molecular orbital calculations (MNDO, AM1, and PM3) of the energies of the optimized structures of reactants, presumed intermediates, and products of the reactions, together with estimates of the energy barriers for the minimum energy reaction pathways, were used to understand the nature of the reaction mechanism.

  DOI：

  10.1021/jo00015a023

文献信息

• Unusual behavior of carbocations derived from 2-cumyladamantan-2-ol and its η6-Cr(CO)3 complex
  作者：Ibraheem T. Badejo、Heajin Choi、James L. Fry

  DOI：10.1016/s0040-4039(00)80609-7

  日期：1988.1
• CHOI H.; PINKERTON A. A.; FRY J. L., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 4, 225-226
  作者：CHOI H.、 PINKERTON A. A.、 FRY J. L.

  DOI：——

  日期：——
• BADEJO, IBRAHEEM T.;CHOI, HEAJIN;FRY, JAMES L., TETRAHEDRON LETT., 29,(1988) N 38, C. 4787-4790
  作者：BADEJO, IBRAHEEM T.、CHOI, HEAJIN、FRY, JAMES L.

  DOI：——

  日期：——
• Unstable compounds. Synthesis, structure, and experimental and computational carbocation chemistry of 2-cumyladamantan-2-ol and its chromium .eta.6-Cr(CO)3 complex
  作者：Ibraheem T. Badejo、Heajin Choi、Christa M. Hockensmith、Rafik Karaman、A. Alan Pinkerton、James L. Fry

  DOI：10.1021/jo00015a023

  日期：1991.7

  Structures of the title alcohol (1) and its chromium tricarbonyl complex (1a), were determined by single-crystal X-ray diffraction methods and were found to be very similar. Both of the alcohols were subjected to treatment with strong acids, and the behavior of the resulting carbocations was studied. Little difference between the two systems was noted. Both gave a mixture of predominantly phenyl- and methyl-shifted olefinic and cyclopropane dehydration products under various reaction conditions. These presumably arose from the corresponding rearranged cations. H-1 and C-13 NMR spectra of the cation derived from the title alcohol were obtained under stable ion conditions. Trapping of this species by triethylsilane at -78-degrees-C produced a 96% yield of 2-cumyladamantane. Semiempirical molecular orbital calculations (MNDO, AM1, and PM3) of the energies of the optimized structures of reactants, presumed intermediates, and products of the reactions, together with estimates of the energy barriers for the minimum energy reaction pathways, were used to understand the nature of the reaction mechanism.