3-chloro-3-chlorosulfenylspiro-4-one | 155914-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-chloro-3-chlorosulfenylspiro-4-one
• 英文别名: 3-chloro-3-chlorosulfenylspiro(chroman-2,1'-cyclohexan)-4-one；(3-Chloro-4-oxospiro[chromene-2,1'-cyclohexane]-3-yl) thiohypochlorite
• CAS: 155914-01-5
• 化学式: C₁₄H₁₄Cl₂O₂S
• 分子量: 317.236
• InChiKey: XLTKESCNPOJVGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±45.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-3-chlorosulfenylspiro-4-one 在 臭氧 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.25h， 生成 spiro-3,4-dione
  参考文献：
  名称：

  New Reactions of Thione S-(tert-Alkylimides).

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.53-0284
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 氯化亚砜 作用下， 反应 14.0h， 生成 3-chloro-3-chlorosulfenylspiro-4-one
  参考文献：
  名称：

  A new reaction of α-chloro-α-chlorosulfenyl ketones: facile syntheses of 3,3-dichloro- and 3-chloro-chroman-4-ones and thiochroman-4-ones

  摘要：

  DOI：

  10.1016/s0040-4020(01)90434-x

文献信息

• [4 + 2]-Cycloaddition Reactions Involving α-Oxo Thioketone Intermediates
  作者：Mohamed I. Hegab、Abd El-Galil A. Amr、Farouk M. E. Abdel-Megeid

  DOI：10.1515/znb-2002-0813

  日期：2002.8.1

  α-Chloro β-oxo sulfenyl chlorides 2 were reduced by iodide ions to the corresponding α-oxo thioketones 3 which dimerized in situ in a hetero-[4 + 2] cycloaddition to give the 1,3,4- oxadithiin derivatives 4. The α-oxo thioketones 3, in situ, cyclized also with 2,3-dimethyl-1,3- butadiene to give the corresponding adducts 5 and only in case of the oxo thioketone intermediate 3d two products 4d and 5d were obtained. Also, The α-oxo thioketones 3a,c, underwent in situ, cycloaddition with furan to give the corresponding adducts 6a,c together with the corresponding thioketone dimers 4a,c. When this reaction was carried out in the presence of diethyl acetylenedicarboxylate or chalcone derivative 8, only the oxo thioketone dimers 4a-d were obtained.

  α-氯β-氧基磺酰氯化物2被碘离子还原为相应的α-氧基硫酮3，在异[4 + 2]环加成中原位二聚形成1,3,4-氧硫代噻吩衍生物4。α-氧基硫酮3也在原位与2,3-二甲基-1,3-丁二烯发生环化反应，形成相应的加合物5，仅在氧基硫酮中间体3d的情况下得到两种产物4d和5d。此外，α-氧基硫酮3a、c在原位与呋喃发生环加成反应，形成相应的加合物6a、c以及相应的硫酮二聚体4a、c。当在乙酸二乙酯乙炔二羧酸酯或查尔康衍生物8存在的情况下进行此反应时，仅得到氧基硫酮二聚体4a-d。
• A new reaction of α-chloro-α-chlorosulfenyl ketones: facile syntheses of 3,3-dichloro- and 3-chloro-chroman-4-ones and thiochroman-4-ones
  作者：Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/s0040-4020(01)90434-x

  日期：1994.4
• New Reactions with Thiosulfines/Dithiiranes: Cycloadditions Leading to Dispiro Derivatives of 1,2,4-Trithiolane.
  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.53-0133

  日期：——

  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.
• 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.
• Facile Regioselective Synthesis, Molecular Dynamics Study, and Antioxidant Activity of Some 3′H,4H-Spiro[chromene-3,2′-[1,3,4]thiadiazol]-4-ones
  作者：T. El Malah、I. S. Abd-Elsalam、A. M. Saleh、A. A. El-Rashedy、M. I. Hegab

  DOI：10.1134/s1070428023070126

  日期：2023.7