1,2-dimethyl-4-(methylsulfinyl)benzene | 38417-53-7

• 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: 1,2-dimethyl-4-(methylsulfinyl)benzene
• 英文别名: 3,4-dimethylphenyl methyl sulfoxide；methyl 3,4-xylyl sulfoxide；3,4-Dimethylphenylmethylsulfoxide；1,2-dimethyl-4-methylsulfinylbenzene
• CAS: 38417-53-7
• 化学式: C₉H₁₂OS
• mdl: MFCD18785706
• 分子量: 168.26
• InChiKey: ICPICMYTXUBOQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  1,2-dimethyl-4-(methylsulfinyl)benzene 在 (S)-isoleucyl-(S)-2-phenylglycine 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (S)-methyl 3,4-xylyl sulfoxide 、 methyl 3,4-xylyl sulfoxide
  参考文献：
  名称：

  Predominant (S)-Enantioselective Inclusion of Aryl Methyl Sulfoxides by (S)-Isoleucyl-(S)-phenylglycines

  摘要：

  In terms of chiral recognition for racemic aryl methyl sulfoxides in the solid state, three kinds of crystalline (S)-alkylglycyl-(S)-phenylglycines were examined as potential dipeptides host molecules. When (S)-alanyl-(S)-phenylglycines [(S,S)-Ala-Phg] crystallized with aryl methyl sulfoxides, the stereochemistry of preferentially included sulfoxides depended on the individual shapes of the sulfoxides and the enantiomeric excess was relatively low. Although (S)-leucyl-(S)phenylglycines [(S,S)-Leu-Phg] and (S)-isoleucyl-(S)-phenylglycines [(S,S)-Ile-Phg] mainly included the S-form of aryl methyl sulfoxides, the enantiomeric recognition of (S,S)-Ile-Phg was superior to that of (S,S)-Leu-Phg. Single-crystal X-ray analysis of these inclusion compounds revealed that the dipeptide molecules self-assembled to form layer structures and included sulfoxides between these layers through hydrogen bonding between the proton of (+)NH(3) and the oxygen of the sulfoxide. Besides these host-guest interactions, the phenyl groups of the sulfoxides interacted with each other through the phenyl-phenyl interaction. Two adjacent homochiral sulfoxides make a pair having a 2-fold screw axis along the channel cavity. Thus, the self-recognition of sulfoxides made 2(1) helical column structures and had high enantioselectivity.

  DOI：

  10.1021/jo902197k
• 作为产物：
  描述：

  1,2-Dimethyl-4-(methylthio)benzene 在 perborate 作用下， 以 溶剂黄146 为溶剂， 生成 1,2-dimethyl-4-(methylsulfinyl)benzene
  参考文献：
  名称：

  冰醋酸中有机硫化物过硼酸盐氧化的机理研究

  摘要：

  过硼酸盐在冰醋酸中溶液老化生成过氧乙酸，有机硫化物过氧乙酸氧化较快。过硼酸盐在乙酸中的新鲜溶液氧化是平稳的，是二级的，不受酸催化；过氧化氢是氧化物质。氧化符合 Exner 和 Hammett 关系。

  DOI：

  10.1002/1099-0690(200010)2000:19<3261::aid-ejoc3261>3.0.co;2-u

文献信息

• Visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO
  作者：Mukund M. D. Pramanik、Namrata Rastogi

  DOI：10.1039/c6cc04142f

  日期：——

  The visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO is illustrated.

  示出了使用DMSO的可见光催化的（杂）芳基重氮盐的甲基磺酰氧化。
• On the Mechanism of the Perborate Oxidation of Organic Sulfides in Glacial Acetic Acid
  作者：Chockalingam Karunakaran、Ramasamy Kamalam

  DOI：10.1002/1099-0690(200010)2000:19<3261::aid-ejoc3261>3.0.co;2-u

  日期：2000.10

  Perborate solution in glacial acetic acid generates peracetic acid on aging, and the peracetic acid oxidation of organic sulfides is fast. The oxidation with fresh solutions of perborate in acetic acid is smooth and is second order, uncatalyzed by acid; hydrogen peroxide is the oxidizing species. The oxidation conforms to the Exner and Hammett relations.

  过硼酸盐在冰醋酸中溶液老化生成过氧乙酸，有机硫化物过氧乙酸氧化较快。过硼酸盐在乙酸中的新鲜溶液氧化是平稳的，是二级的，不受酸催化；过氧化氢是氧化物质。氧化符合 Exner 和 Hammett 关系。
• 6-(SULFONYLARYL)PYRIDO[2,3-D]PYRIMIDIN-7(8H)-ONES FOR THE TREATMENT OF CNS DISORDERS
  申请人：Campbell David

  公开号：US20130252966A1

  公开（公告）日：2013-09-26

  Provided herein are PAK inhibitors and methods of utilizing PAK inhibitors for the treatment of CNS disorders such as neuropsychiatric disorders.

  本文提供了PAK抑制剂和利用PAK抑制剂治疗中枢神经系统疾病，如神经精神疾病的方法。
• PAK INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：Afraxis, Inc.

  公开号：US20130158043A1

  公开（公告）日：2013-06-20

  Provided herein are methods of utilizing PAK inhibitors for the treatment of cancer. Further provided herein are compounds and formulations utilized for the treatment of cancer.

  本文提供了利用PAK抑制剂治疗癌症的方法。此外，还提供了用于治疗癌症的化合物和配方。
• 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.