2,5-二甲基-3,4-二苯基己烷-3,4-二醇 | 59214-60-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2,5-二甲基-3,4-二苯基己烷-3,4-二醇
• 英文名称: 2,5-Dimethyl-3,4-diphenyl-3,4-hexandiol
• 英文别名: dl-Isobutyrophenon-pinakol；2,5-Dimethyl-3,4-diphenylhexane-3,4-diol
• CAS: 59214-60-7
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: JALZIUYMGTXWGF-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  433.6±40.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  异丁酰苯 以 异丙醇 为溶剂， 生成 2,5-二甲基-3,4-二苯基己烷-3,4-二醇
  参考文献：
  名称：

  Rate constants for degenerate hydrogen atom exchange between .alpha.-hydroxy radicals and ketones

  摘要：

  When a phenyl ketone is irradiated in the presence of 1-phenylethanol, the photoproducts include acetophenone pinacol, the pinacol from the other phenyl ketone, a mixed pinacol, and acetophenone, which is formed by irreversible hydrogen atom exchange between the hemipinacol radical of acetophenone and the other ketone. Rate constants for this hydrogen atom exchange between the hemipinacol radical of acetophenone and three other ketones were determined by measuring how acetophenone yields depend on the concentration of the other ketone. Comparable measurements were made for p-chloroacetophenone formation by irradiating acetophenone in the presence of 1-(p-chlorophenyl)ethanol. As the starting ketone concentration increases, so does the amount of exchange relative to pinacol, while the pinacol content reflects decreasing amounts of the original alcohol. Exchange is measurable at ketone concentrations below 0.01 M and is complete by 0.1 M. Rate constants k(ex) of 3.7, 6.3, 4.2, and 8.6 X 10(3) M-1 S-1 were deduced for hydrogen transfer to propiophenone, isobutyrophenone, p-methylacetophenone, and p-chloroacetophenone, respectively, based on a competing rate constant for radical coupling of 2 x 10(9) M-1 s-1. Equilibrium constants for the hydrogen transfer were determined from the product ratios obtained by irradiating a mixture of two ketones with 2-propanol; from these k(-ex) values of 11.5, 57, 13, and 1.8 X 10(3) M-1 s-1, respectively, were deduced for hydrogen transfer to acetophenone from the four other ketone hemipinacol radicals. These exchange rate constants depend more on the structure of the radical than on that of the ketone. Actual quantum yields for pinacol formation do not exceed 50%; this maximum quantum efficiency rises to 71% for 1-phenylethanol-O-d. From this inverse isotope effect it is concluded that half the reaction of triplet acetophenone with 1-phenylethanol involves abstraction of an OH hydrogen followed by disproportionation of the initial radical pair back to reactants.

  DOI：

  10.1021/j100152a049

文献信息

• Enantioselective Cathodic Reduction of Some Prochiral Ketones in the Presence of (1<i>R</i>,2<i>S</i>)-(-)-<i>N</i>,<i>N</i>-Dimethylephedrinium Tetrafluoroborate at a Mercury Pool Cathode
  作者：Ashok K. Yadav、Arpita Singh

  DOI：10.1246/bcsj.75.587

  日期：2002.3

  The enantioselective cathodic reduction of some prochiral ketones viz. acetophenone (I), propiophenone (II), butyrophenone (III), valerophenone (IV), isobutyrophenone (V), and pivalophenone (VI) has been accomplished at a mercury pool cathode in N,N-dimethylformamide (DMF)–water (90 : 10) using tetrabutylammonium fluoroborate (TBA·BF4) as a supporting electrolyte in the presence of (1R,2S)-(-)-N,N

  一些前手性酮的对映选择性阴极还原，即。苯乙酮 (I)、苯丙酮 (II)、丁苯酮 (III)、戊苯酮 (IV)、异丁苯酮 (V) 和新戊苯酮 (VI) 已在 N,N-二甲基甲酰胺 (DMF)-水中的汞池阴极上完成（ 90 : 10) 在 (1R,2S)-(-)-N,N-二甲基麻黄鎓四氟硼酸盐 (DET) 存在下，使用四丁基氟硼酸铵 (TBA·BF4) 作为支持电解质。已经进行了循环伏安研究，并提出了该过程的可能机制。
• Claus, Journal fur praktische Chemie (Leipzig 1954), 1892, vol. <2> 46, p. 481 Anm.
  作者：Claus

  DOI：——

  日期：——
• Horner, Leopold; Dickerhof, Karlheinz, Liebigs Annalen der Chemie, 1984, # 6, p. 1240 - 1258
  作者：Horner, Leopold、Dickerhof, Karlheinz

  DOI：——

  日期：——
• Rate constants for degenerate hydrogen atom exchange between .alpha.-hydroxy radicals and ketones
  作者：Peter J. Wagner、Yuanda Zhang、Allen E. Puchalski

  DOI：10.1021/j100152a049

  日期：1993.12

  When a phenyl ketone is irradiated in the presence of 1-phenylethanol, the photoproducts include acetophenone pinacol, the pinacol from the other phenyl ketone, a mixed pinacol, and acetophenone, which is formed by irreversible hydrogen atom exchange between the hemipinacol radical of acetophenone and the other ketone. Rate constants for this hydrogen atom exchange between the hemipinacol radical of acetophenone and three other ketones were determined by measuring how acetophenone yields depend on the concentration of the other ketone. Comparable measurements were made for p-chloroacetophenone formation by irradiating acetophenone in the presence of 1-(p-chlorophenyl)ethanol. As the starting ketone concentration increases, so does the amount of exchange relative to pinacol, while the pinacol content reflects decreasing amounts of the original alcohol. Exchange is measurable at ketone concentrations below 0.01 M and is complete by 0.1 M. Rate constants k(ex) of 3.7, 6.3, 4.2, and 8.6 X 10(3) M-1 S-1 were deduced for hydrogen transfer to propiophenone, isobutyrophenone, p-methylacetophenone, and p-chloroacetophenone, respectively, based on a competing rate constant for radical coupling of 2 x 10(9) M-1 s-1. Equilibrium constants for the hydrogen transfer were determined from the product ratios obtained by irradiating a mixture of two ketones with 2-propanol; from these k(-ex) values of 11.5, 57, 13, and 1.8 X 10(3) M-1 s-1, respectively, were deduced for hydrogen transfer to acetophenone from the four other ketone hemipinacol radicals. These exchange rate constants depend more on the structure of the radical than on that of the ketone. Actual quantum yields for pinacol formation do not exceed 50%; this maximum quantum efficiency rises to 71% for 1-phenylethanol-O-d. From this inverse isotope effect it is concluded that half the reaction of triplet acetophenone with 1-phenylethanol involves abstraction of an OH hydrogen followed by disproportionation of the initial radical pair back to reactants.
• Leimner, Juergen; Weyerstahl, Peter, Chemische Berichte, 1982, vol. 115, # 12, p. 3697 - 3705
  作者：Leimner, Juergen、Weyerstahl, Peter

  DOI：——

  日期：——