p-Neopentyltoluol | 24797-40-8

• 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: p-Neopentyltoluol
• 英文别名: 1-(2,2-Dimethylpropyl)-4-methylbenzene
• CAS: 24797-40-8
• 化学式: C₁₂H₁₈
• 分子量: 162.275
• InChiKey: XXIILALDVWROQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  212-214 °C
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  p-Neopentyltoluol 在 potassium permanganate 作用下， 以 叔丁醇 为溶剂， 生成 4-Pivaloyl-benzoesaeure
  参考文献：
  名称：

  新戊基衍生物的化学：I.苄基格氏试剂与叔丁基卤化物的反应性。新戊基苯甲酸的合成及热力学解离常数

  摘要：

  苄基卤化镁与叔丁基卤的反应除生成新戊基苯外，还生成邻位和对叔丁基甲苯。已经研究了（i）两种反应物中都存在的卤原子，（ii）所用镁的纯度，（iii）进行反应的溶剂和（iv）取代基中的取代基的影响。格氏试剂的芳环。还研究了叔丁基氯化镁与4-烷基苄基氯的反应。

  DOI：

  10.1016/s0040-4020(01)92843-1
• 作为产物：
  描述：

  4-methylbenzyl 2,2,-dimethylpropanoate 生成 p-Neopentyltoluol
  参考文献：
  名称：

  Hilborn J. W., MacKnight E., Pincock J. A., Wedge P. J., J. Amer. Chem. Soc, 116 (1994) N 8, S 3337- 3346

  摘要：

  DOI：

文献信息

• A novel synthesis of neopentylbenzenes
  作者：A. R. Bassindale、C. Eaborn、D. R. M. Walton

  DOI：10.1039/j39690002505

  日期：——

  Benzyl chlorides react with t-butyl-lithium in a mixture of pentane and hexane to give neopentylbenzenes, XC6H4·CH2But. Yields were (X =) H, 75; o-Me, 25; m-Me, 55; p-Me, 62; m-F, 70; p-F, 70; m-Cl, 60; p-Cl, 69; p-Br, 60%.

  苄基氯与戊烷和己烷的叔丁基锂反应，生成新戊基苯XC 6 H 4 ·CH 2 Bu t。产率为（X ＝）H，75； [M + H] +。o -Me，25；m -Me，55；p -Me，62； n。m -F，70；p -F，70；m -Cl，60；m / z。对氯，69；m / z。对溴，60％。
• Chemistry of the tert-butyl radical: polar character, .rho. value for reaction with toluenes, and the effect of radical polarity on the ratio of benzylic hydrogen abstraction to addition to aromatic rings
  作者：William A. Pryor、Felicia Y. Tang、Robert H. Tang、Daniel F. Church

  DOI：10.1021/ja00374a031

  日期：1982.5
• Reactivity of 3,6-dimethoxy-3, 6-dimethylcyclohexa-1, 4-diene: nuclear versus benzylic nucleophilic substitution
  作者：Francisco Alonso、Isidoro Barba、Miguel Yus

  DOI：10.1016/s0040-4020(01)89773-8

  日期：1990.1
• Steric effects in hydrogen atom abstractions
  作者：William D. Totherow、Gerald J. Gleicher

  DOI：10.1021/ja01053a043

  日期：1969.12
• Anodic oxidation of .alpha.-substituted p-xylenes. Electronic and stereoelectronic effects of .alpha.-substituents in the deprotonation of alkylaromatic radical cations
  作者：Enrico Baciocchi、Mario Mattioli、Roberta Romano、Renzo Ruzziconi

  DOI：10.1021/jo00025a036

  日期：1991.12

  The effect of alpha-substituents on the deprotonation rate from the benzylic position of alkylaromatic radical cations, k(CH2Z)/k(CH3), has been investigated by determining the intramolecular selectivity in the anodic oxidation in acetic acid of alpha-Z-substituted p-xylenes 1 (Z = H, OMe, OH, Me, tert-butyl, OAc, COOMe, CN), 5,6-dimethylindan 4 (R = H), and 2,2,5,6-tetramethylindan 4 (R = Me). Some oxidations induced by CAN have also been carried out. It has been found that, with the exception of when Z = tert-butyl, the deprotonation rate of I.+ is always faster from the CH2Z group than from the CH3 group, independently of the electron-donating or electron-withdrawing nature of Z. The electron-donating groups (OH, OMe, Me), however, exert a larger effect than the electron-withdrawing ones (COOMe, CN). The negligible deprotonation rate from CH2-t-Bu has been ascribed to stereoelectronic effects (the bulky tert-butyl group does not allow the C-H bonds to be collinear with the pi-system), the suggestion being nicely confirmed by the observation that the deprotonation rate from the position 1(3), relative to that from the 5(6)-methyl group, is almost identical in the radical cations of 4 (R = H and Me). The effect of the other alpha-substituents is mainly of electronic nature and has been rationalized on the basis of a variable transition-state structure for the deprotonation process. It is suggested that with +R groups most of the charge, in the transition state, has been transferred to the C(alpha)-H bond where it can be stabilized by the alpha-substituent. With electron-withdrawing groups less charge transfer has taken place and the rate-enhancing effects of these groups is ascribed to their capability to significantly decrease the strength of the C(alpha)-H bond.