Di(1-adamantyl)-tert-butylmethanol | 80514-85-8

• 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: Di(1-adamantyl)-tert-butylmethanol
• 英文别名: 1,1-Bis(1-adamantyl)-2,2-dimethylpropan-1-ol
• CAS: 80514-85-8
• 化学式: C₂₅H₄₀O
• 分子量: 356.592
• InChiKey: DGHUHIHQHZQUHT-UHFFFAOYSA-N

物化性质

• 沸点：
  432.3±13.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  8.0
• 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：

  Di(1-adamantyl)-tert-butylmethanol 以 十二烷 为溶剂， 生成 乙基,1,1-二甲基-(9CI) 、
  参考文献：
  名称：

  Thermolysis of highly congested tert-butyldialkylcarbinols with bridgehead substituents: molecular-mechanics treatment of radical-forming processes

  摘要：

  DOI：

  10.1021/jo00144a020
• 作为产物：
  描述：

  1-溴金刚烷 、 1-adamantyl tert-butyl ketone 在 lithium 作用下， 以 乙醚 为溶剂， 以16%的产率得到Di(1-adamantyl)-tert-butylmethanol
  参考文献：
  名称：

  Thermolysis of highly congested tert-butyldialkylcarbinols with bridgehead substituents: molecular-mechanics treatment of radical-forming processes

  摘要：

  DOI：

  10.1021/jo00144a020

文献信息

• Reactions of thermally generated tert-butyl and di(tert-alkyl) ketyl radicals in toluene: cage effects and hydrogen transfer
  作者：John S. Lomas、Sylvette Briand、Dominique Fain

  DOI：10.1021/jo00001a034

  日期：1991.1

  Thermolysis of di(1-adamantyl)-tert-butylmethanol (2a) in toluene at 145-185-degrees-C gives mainly bibenzyl, di(1-adamantyl) ketone, di(1-adamantyl)methanol, and the cross-product, 1,1-di(1-adamantyl)-2-phenylethanol. In the presence of benzophenone (BP) or benzenethiols as hydrogen-accepting and hydrogen-donating radical scavengers, respectively, the di(1-adamantyl)methanol/di(1-adamantyl) ketone ratio tends to steady values as the scavenger/2a ratio is increased, while the cross-product disappears. At 165-degrees-C the secondary alcohol minimum is 8% (BP) and the ketone minimum 11% (thiol). These represent the contributions of geminate hydrogen atom transfer reactions to the overall yields, i.e., the cage effects. With BP the major cross-product is 1,1,2-triphenylethanol. Products from the self- and cross-reactions of benzyl and thiyl radicals are found when thiol is present, the diaryl disulfide predominating at high thiol concentration. In both cases, cross-products resulting from reaction of the tert-butyl radical with the scavenger-derived radical are detected in small amounts, being of greater importance in deuteriated toluene. The tert-butyl radical is considered, therefore, to be less reactive in hydrogen atom abstraction than the 1-adamantyl radical. Cage effects for other di(tert-alkyl)-tert-butylmethanols that thermolyze with exclusive t-Bu-C bond fission have also been measured and the product composition of the scavenger-free reaction interpreted by kinetic simulation based on the steady state approximation. Rate constants for hydrogen abstraction by the tert-butyl radical from toluene are not accurately determined by this procedure but seem, nevertheless, to indicate that the literature value (14.4 M-1 s-1 at 48-degrees-C) is an overestimate. Solvent hydrogen abstraction by the ketyl radical shows a small but well-defined steric effect.
• Formation of alkyl carbanions by alkoxide fragmentation in HMPT
  作者：John S. Lomas、Jacques Emile Dubois

  DOI：10.1021/jo00185a064

  日期：1984.6
• LOMAS, JOHN S.;BRIAND, SYLVETTE;FAIN, DOMINIQUE, J. ORG. CHEM., 56,(1991) N, C. 166-175
  作者：LOMAS, JOHN S.、BRIAND, SYLVETTE、FAIN, DOMINIQUE

  DOI：——

  日期：——
• Thermolysis of highly congested tert-butyldialkylcarbinols with bridgehead substituents: molecular-mechanics treatment of radical-forming processes
  作者：John S. Lomas、Jacques Emile Dubois

  DOI：10.1021/jo00144a020

  日期：1982.11