(2-Methyl-benzyl)-methyl-sulfoxid | 15733-12-7

• 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-Methyl-benzyl)-methyl-sulfoxid
• 英文别名: 1-Methyl-2-(methylsulfinylmethyl)benzene；1-methyl-2-(methylsulfinylmethyl)benzene
• CAS: 15733-12-7
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: INBGFMNKIKRPNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-Methyl-benzyl)-methyl-sulfoxid 、 (R)-phenylglycyl-(R)-phenylglycine 在 盐酸 、 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  Enantioselective Inclusion of Methyl Phenyl Sulfoxides and Benzyl Methyl Sulfoxides by (R)-Phenylglycyl-(R)-phenylglycine and the Crystal Structures of the Inclusion Cavities

  摘要：

  Crystalline (R)-phenylglycyl-(R)-phenylglycine [(R,R)-1] includes methyl phenyl sulfoxides (2 and 3) and benzyl methyl sulfoxides (4) with high enantioselectivity. The dipeptide exhibited different stereoselectivity depending on four structural isomers of methyl tolyl sulfoxide (C8H10OS): R for methyl 2-tolyl sulfoxide, S for methyl 3-tolyl sulfoxide, and racemic for methyl 4-tolyl sulfoxide. A structural isomer, benzyl methyl sulfoxide, was included in racemic form. Chlorophenyl methyl sulfoxides 3 (C7H7ClOS) with a similar volume showed the same enantioselectivity for their recognition. By single-crystal X-ray analyses of these inclusion compounds, it was elucidated that (R,R)-1 molecules self-assembled to form layer structures and included the sulfoxides between these layers and that the origin of the enantioselectivity based on chiral cavities was induced by conformation of the C-terminal phenyl group of the dipeptide. The relative position between the ammonio proton and the C-terminal phenyl group in one molecule of the dipeptide determined the stereochemistry of the methyl sulfinyl groups to be recognized. Various positional isomers of methyl xylyl sulfoxide having the formula of C9H12OS were subjected to the enantioselective inclusion by (R,R)-1 crystals and these results are also discussed.

  DOI：

  10.1021/jo991051l
• 作为产物：
  描述：

  邻甲基氯化苄 在 双氧水 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 (2-Methyl-benzyl)-methyl-sulfoxid
  参考文献：
  名称：

  一些芳基烷基亚砜的反应和质谱

  摘要：

  在热解和质谱分析行为中比较了亚砜Ph·[CH 2 ] n ·SO·Me（n = 0–4）。在热解过程中，发生了β-消除或重排，但在质谱图中未观察到类似的作用。通过一系列复杂的反应，尝试制备一种亚砜实际上产生了下一个更高的同系物。

  DOI：

  10.1039/j39670000302

文献信息

• Lorenz,D., Zeitschrift fur Chemie, 1969, vol. 9, p. 141
  作者：Lorenz,D.

  DOI：——

  日期：——
• Enantioselective Inclusion of Methyl Phenyl Sulfoxides and Benzyl Methyl Sulfoxides by (<i>R</i>)-Phenylglycyl-(<i>R</i>)-phenylglycine and the Crystal Structures of the Inclusion Cavities
  作者：Motohiro Akazome、Yuki Ueno、Haruko Ooiso、Katsuyuki Ogura

  DOI：10.1021/jo991051l

  日期：2000.1.1

  Crystalline (R)-phenylglycyl-(R)-phenylglycine [(R,R)-1] includes methyl phenyl sulfoxides (2 and 3) and benzyl methyl sulfoxides (4) with high enantioselectivity. The dipeptide exhibited different stereoselectivity depending on four structural isomers of methyl tolyl sulfoxide (C8H10OS): R for methyl 2-tolyl sulfoxide, S for methyl 3-tolyl sulfoxide, and racemic for methyl 4-tolyl sulfoxide. A structural isomer, benzyl methyl sulfoxide, was included in racemic form. Chlorophenyl methyl sulfoxides 3 (C7H7ClOS) with a similar volume showed the same enantioselectivity for their recognition. By single-crystal X-ray analyses of these inclusion compounds, it was elucidated that (R,R)-1 molecules self-assembled to form layer structures and included the sulfoxides between these layers and that the origin of the enantioselectivity based on chiral cavities was induced by conformation of the C-terminal phenyl group of the dipeptide. The relative position between the ammonio proton and the C-terminal phenyl group in one molecule of the dipeptide determined the stereochemistry of the methyl sulfinyl groups to be recognized. Various positional isomers of methyl xylyl sulfoxide having the formula of C9H12OS were subjected to the enantioselective inclusion by (R,R)-1 crystals and these results are also discussed.
• Reactions and mass spectra of some aryl-alkyl sulphoxides
  作者：I. D. Entwistle、R. A. W. Johnstone、B. J. Millard

  DOI：10.1039/j39670000302

  日期：——

  sulphoxides Ph·[CH2]n·SO·Me (n= 0–4) were compared in pyrolytic and mass spectrometric behaviour. On pyrolysis either β-elimination or rearrangement occurred, but similar effects were not observed in the mass spectra. The attempted preparation of one of the sulphoxides actually yielded the next higher homologue by a complex series of reactions.

  在热解和质谱分析行为中比较了亚砜Ph·[CH 2 ] n ·SO·Me（n = 0–4）。在热解过程中，发生了β-消除或重排，但在质谱图中未观察到类似的作用。通过一系列复杂的反应，尝试制备一种亚砜实际上产生了下一个更高的同系物。