(2RS,3SR)-2-chloro-3-ethyl-1,2,3,4-tetrahydro-3-methyl-1-oxonaphthalene-2-sulfenyl chloride | 228122-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2RS,3SR)-2-chloro-3-ethyl-1,2,3,4-tetrahydro-3-methyl-1-oxonaphthalene-2-sulfenyl chloride
• 英文别名: (2-chloro-3-ethyl-3-methyl-1-oxo-4H-naphthalen-2-yl) thiohypochlorite
• CAS: 228122-76-7
• 化学式: C₁₃H₁₄Cl₂OS
• 分子量: 289.226
• InChiKey: ONFKMMUFISGBPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-2-chloro-3-ethyl-1,2,3,4-tetrahydro-3-methyl-1-oxonaphthalene-2-sulfenyl chloride 在 吗啉 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 3.0h， 生成 trans-3,3''-diethyl-1,1'',2,2'',3,3'',4,4''-octahydro-3,3''-methyldispirotrithiolane-5',2''-naphthalene>-1,1''-dione
  参考文献：
  名称：

  New Reactions with Thiosulfines/Dithiiranes: Cycloadditions Leading to Dispiro Derivatives of 1,2,4-Trithiolane.

  摘要：

  The beta-oxo thiosulfines 8, generated by 'unzipping' of the corresponding acetyl alpha-chloroalkyl disulfides 11 with morpholine, are partially converted into the corresponding thioketones 12 which then cycloadd to 8 to give the observed cis-and trans-1,2,4-trithiolanes 15. The unsymmetrical Diels-Alder dimerization of 12 plays only a minor role. The new heterocycles thus obtained have been characterized spectroscopically and by X-ray crystallography.

  DOI：

  10.3891/acta.chem.scand.53-0133
• 作为产物：
  描述：

  3-乙基-3-甲基-2,4-二氢萘-1-酮 在 氯化亚砜 作用下， 反应 3.0h， 以43%的产率得到(2RS,3SR)-2-chloro-3-ethyl-1,2,3,4-tetrahydro-3-methyl-1-oxonaphthalene-2-sulfenyl chloride
  参考文献：
  名称：

  New Reactions with Thiosulfines/Dithiiranes: Cycloadditions Leading to Dispiro Derivatives of 1,2,4-Trithiolane.

  摘要：

  The beta-oxo thiosulfines 8, generated by 'unzipping' of the corresponding acetyl alpha-chloroalkyl disulfides 11 with morpholine, are partially converted into the corresponding thioketones 12 which then cycloadd to 8 to give the observed cis-and trans-1,2,4-trithiolanes 15. The unsymmetrical Diels-Alder dimerization of 12 plays only a minor role. The new heterocycles thus obtained have been characterized spectroscopically and by X-ray crystallography.

  DOI：

  10.3891/acta.chem.scand.53-0133

文献信息

• New Reactions of Thione S-(tert-Alkylimides).
  作者：Mohamed I. Hegab、Farouk M. E. Abdel-Megeid、Farouk A. Gad、Sayed A. Shiba、Inger Søtofte、Jørgen Møller、Alexander Senning、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0284

  日期：——

  Two new alpha-chloro sulfenyl chlorides 1, four new 2-thioxo-1-tetralone S-imides 2 (X = CH2), and one new 3-thioxochroman-4-one S-imide 2 (X = O) have been prepared and characterized by comprehensive spectroscopy and, in one case, an X-ray crystal structure determination. Pyrolysis of 2 leads to the corresponding 1,2,4-trithiolanes 3 after extensive sulfur scrambling. Addition of arenethiols to 2 (R-5 = t-Bu), but not 2 (R-5 = 1-adamantyl), leads to the corresponding adducts 13 with an unusual dithioacetal structure. Ozonolysis of 2 gives the corresponding alpha-diketones such as 16.