(1-chloro-1-methyl)ethyl phenyl sulfoxide | 26910-41-8

• 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: (1-chloro-1-methyl)ethyl phenyl sulfoxide
• 英文别名: Phenyl-α-(2-chlorisopropyl)sulfoxid；1-Chlor-1-methylethylphenylsulfoxid；Phenyl-chlorisopropylsulfoxid；2-Chloropropan-2-ylsulfinylbenzene
• CAS: 26910-41-8
• 化学式: C₉H₁₁ClOS
• 分子量: 202.705
• InChiKey: CVSRZWCBORHTOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [(1-甲基乙基)亚磺酰]-苯 在 1-氯苯并三氮唑 作用下， 以 乙腈 为溶剂， 生成 (1-chloro-1-methyl)ethyl phenyl sulfoxide
  参考文献：
  名称：

  N-氯苯并三唑α-氯化亚砜的动力学

  摘要：

  在吡啶存在下，在乙腈中用N-氯苯并三唑进行芳基甲基和芳基异丙基亚砜的α-氯化反应遵循二级动力学。该反应受供电子基团的促进，并且受到明显的动力学同位素效应（K H / K D）。根据动力学数据，提出了两个亚砜系列的通用反应机理，其中涉及形成中间体的氯-氧磺酸盐，在速率确定步骤中，该盐在碱的作用下分解成α-氯亚砜。

  DOI：

  10.1039/p29750000218

文献信息

• Synthesis of α-halogeno-sulphoxides
  作者：M. Cinquini、S. Colonna

  DOI：10.1039/p19720001883

  日期：——

  Reaction of sulphoxides with (dichloroiodo)benzene or with bromine in the presence of pyridine affords the corresponding α-halogeno-sulphoxides. Some reactions of α-halogeno-sulphoxides are here described.

  亚砜与（二氯碘代）苯或与溴在吡啶存在下反应，得到相应的α-卤代亚砜。这里描述了α-卤代亚砜的一些反应。
• Solid-Phase Silica-Gel Catalyzed α-Halogenation of Alkyl Aryl Sulfoxides with<i>N</i>-Halosuccinimides
  作者：Józef Drabowicz

  DOI：10.1055/s-1986-31793

  日期：——
• The Reaction of Sulfoxides with 1-Chlorobenzotriazole
  作者：Mauro CINQUINI、S. COLONNA

  DOI：10.1055/s-1972-21861

  日期：——
• Cinquini,M. et al., Journal of the Chemical Society. Perkin transactions II, 1972, p. 296 - 300
  作者：Cinquini,M. et al.

  DOI：——

  日期：——
• Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model:  Trapping of Radical Intermediates
  作者：Vincent Mutterer、Elena Giménez Arnau、Ann-Therese Karlberg、Jean-Pierre Lepoittevin

  DOI：10.1021/tx9901433

  日期：2000.10.1

  To better understand the skin sensitization mechanism of 15-hydroperoxyabietic acid-like compounds, 2-(1'-hydroperoxy-1'-methylethyl)-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene 7 was synthesized. The allergenic activity of this compound was tested on mice using the local lymph node assay, and further evaluated on guinea pigs using the Freund's complete adjuvant test. Using these methods, hydroperoxide 7 was found to be a strong sensitizer. Radical-trapping experiments were carried out on this compound in the presence of the spin-trapping agent, 1,1,3,3-tetramethylisoindolin-2-yloxyl 17, using light to induce radicals. The formation of carbon-centered radicals derived from compound 7 by intramolecular cyclization of an oxygen-centered radical was observed. The reaction of these intermediates with 17 gave various adducts in a very low yield, but a 1/1 mixture of diastereomers 18a and 18b (0.1% yield) was isolated and characterized, together with compound 19 (0.03% yield). The results suggest that carbon-centered reactive radicals are formed from allylic hydroperoxides and that this could be the possible mechanism involved in allergic contact dermatitis to abietic acid.