4-(4-chlorophenylsulfanyl)butan-2-one | 6110-03-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(4-chlorophenylsulfanyl)butan-2-one
• 英文别名: 4-[(4-chlorophenyl)thio]butan-2-one；4-(4-chlorophenylthio)butan-2-one；<4-Chlor-phenyl>-<3-oxo-butyl>-sulfid；(4-Chlor-phenyl)-(3-oxo-butyl)-sulfid；2-Butanone, 4-[(4-chlorophenyl)thio]-；4-(4-chlorophenyl)sulfanylbutan-2-one
• CAS: 6110-03-8
• 化学式: C₁₀H₁₁ClOS
• mdl: MFCD12146694
• 分子量: 214.716
• InChiKey: UUZMZIDASFKLTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4-(4-chlorophenylsulfanyl)butan-2-one 在 盐酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 (S)-1-acetyl-5-((4-chlorophenylthio)methyl)-4-methyl-3-(1-phenylethyl)-1H-imidazol-2(3H)-one
  参考文献：
  名称：

  Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries

  摘要：

  Functionalized alpha-oximinoketones with beta-alkoxy, beta-alkyl, and beta-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, alpha-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.01.011
• 作为产物：
  描述：

  4,4'-二氯二苯二硫醚 、 丁烯酮 在 indium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以85%的产率得到4-(4-chlorophenylsulfanyl)butan-2-one
  参考文献：
  名称：

  碘化铟 (I) 促进二烷基二硫化物的裂解和随后硫醇阴离子与共轭羰基化合物的迈克尔加成

  摘要：

  碘化铟 (I) 促进二烷基二硫化物的裂解，生成硫醇阴离子，然后在中性条件下轻松加成到 α、β-不饱和酮、醛、羧酸酯和腈，以高产率生成相应的 β-酮或 β-氰基硫化物。有几个二烷基/二芳基二硫化物和活化烯烃参与该反应的例子。

  DOI：

  10.1055/s-2004-825583

文献信息

• Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor–Acceptor Complexes Formed between Two Reactants
  作者：Yi-Ping Cai、Fang-Yuan Nie、Qin-Hua Song

  DOI：10.1021/acs.joc.1c01433

  日期：2021.9.3

  A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor–acceptor (EDA) complexes (KEDA = 145 M–1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400–650

  开发了一种无金属、无光催化剂的光化学系统，用于通过两种反应物之间的电子供体 - 受体 (EDA) 配合物 ( K EDA = 145 M –1 )直接烷基化苯硫酚，N-羟基邻苯二甲酰亚胺酯作为受体和苯硫酚阴离子作为供体，在叔胺的存在下。反应体系中的 EDA 配合物具有广泛的可见光吸收范围（400-650 nm），可以在阳光下有效触发反应。
• Study of the Michael addition of β-cyclodextrin–thiol complexes to conjugated alkenes in water
  作者：N. Srilakshmi Krishnaveni、K. Surendra、K. Rama Rao

  DOI：10.1039/b411736k

  日期：——

  An environmentally benign and highly efficient supramolecular Michael addition of thiols from the secondary side of beta-cyclodextrin to alpha,beta-unsaturated compounds at the primary side in water is described in quantitative yields; products of undesirable side reactions resulting from polymerization are not observed; the use of cyclodextrin precludes the use of either acid or base and the catalyst

  以定量收率描述了一种环境友好，高效的超分子迈克尔加成反应，其将硫从β-环糊精的次级侧添加到水中的初级侧的α，β-不饱和化合物中。没有观察到聚合引起的不良副反应产物；使用环糊精排除了酸或碱的使用，催化剂可以回收再利用。
• Synthesis of novel β-functionalized α-oximinoketones via hetero-Michael addition of alcohols and mercaptans to enones
  作者：Pablo Bernal、Joaquín Tamariz

  DOI：10.1016/j.tetlet.2006.02.125

  日期：2006.4

  β-sulfenyl ketones by hetero-Michael addition of the corresponding alcohols and thiols to enones under acidic and basic conditions. The direct conversion of enones into β-alkoxy and β-sulfenyl α-oximinoketones was also described.

  已经开发了一种通过在酸性和碱性条件下将相应的醇和硫醇杂烯加成到烯酮上来制备β-烷氧基和β-亚磺酰基酮的新方法。还描述了烯酮直接转化为β-烷氧基和β-亚磺酰基α-肟基酮。
• Indium(I) iodide promoted cleavage of dialkyl disulfides — Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
  作者：Brindaban C Ranu、Tanmay Mandal

  DOI：10.1139/v06-065

  日期：2006.5.1

  promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing

  碘化铟 (I) 促进二烷基二硫化物的裂解，生成硫醇阴离子，然后在中性条件下轻松加成到 α,β-不饱和酮、醛、羧酸酯和腈，产生相应的 β-酮硫化物或 β-氰基硫化物。该策略也已用于在氯化铟 (III) 存在下通过硫醇阴离子对环氧化物进行区域选择性亲核开环，产生相应的 β-羟基苯基硫化物。反应通常非常干净、产率高且相当快。因此，利用这种裂解反应开发了合成 β-酮硫化物或 β-氰基硫化物和 β-羟烷基硫化物的简便方法。环氧化物，β-羟基硫化物。
• Synthesis of sulphur heterocyclics—1
  作者：B.D. Tilak、H.S. Desai、C.V. Deshpande、S.K. Jain、V.M. Vaidya

  DOI：10.1016/0040-4020(66)80095-9

  日期：1966.1

  Interaction of 4-methyl-Δ3-thiachromene with polyphosphoric acid (PPA) yields 4-methylthiachroman and a blue thiacyanine dye. The latter is formed from 4-methylthianaphthalenium salt as a precursor.

  的4-甲基- Δ相互作用3 -thiachromene与多磷酸（PPA），得到4- methylthiachroman和蓝色噻菁染料。后者由4-甲基噻吩鎓盐作为前体形成。