2-phenyl-1,3-oxathiolan-5-one | 1564-43-8

• 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: 2-phenyl-1,3-oxathiolan-5-one
• 英文别名: 2-phenyl-1,3-oxothiolan-5-one；2-phenyl-[1,3]oxathiolan-5-one；2-Phenyl-[1,3]oxathiolan-5-on
• CAS: 1564-43-8；119215-82-6；119215-83-7
• 化学式: C₉H₈O₂S
• 分子量: 180.227
• InChiKey: CCPIXSCRYWRMSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  392.1±42.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-phenyl-1,3-oxathiolan-5-one 在 四乙基氟化铵水合物 作用下， 以 乙腈 为溶剂， 生成 4-Fluoro-2-phenyl-1,3-oxathiolan-5-one
  参考文献：
  名称：

  含硫杂环的选择性阳极单氟化：对药物的有效应用

  摘要：

  在含有 Et3Ns3HF 或 Et4NFs4HF 作为支持电解质的 MeCN 中成功地进行了 3-硫杂环戊烷酮、1,3-氧杂硫杂环戊烷酮和 1,3-二硫杂环戊烷酮的区域选择性阳极单氟化。在氟化产物中，与已知抑制剂 manoalide 相比，2-benzyl-4,4-dimethyl-2-ethoxycarbonyl-5-fluoro-3-thiolanone 具有相当甚至更强的体外人 II 型磷脂酶 A2 抑制活性.

  DOI：

  10.1080/10426509708545540
• 作为产物：
  描述：

  α,α'-(benzylidenedithio)diacetic acid 在 sodium hydroxide 、 dipotassium peroxodisulfate 作用下， 以 水 为溶剂， 反应 3.0h， 以23%的产率得到2-phenyl-1,3-oxathiolan-5-one
  参考文献：
  名称：

  制备柱chromatographische Enantiomerentrennung冯synthetischnützlichencyclischen Acetalen †

  摘要：

  综合有用的环缩醛的制备型色谱分离度

  DOI：

  10.1002/hlca.19880710541

文献信息

• Preparative Resolution of Heterocyclic Acetals Derived from Glycine, Mercapto-acetic Acid, ?-Alanine, and Formyl- or Acetylacetic Acid by Recycling Chromatography onChiraspher and Temperature Dependence of Separation Factors
  作者：Joachim N. Kinkel、Urs Gysel、Denis Blaser、Dieter Seebach

  DOI：10.1002/hlca.19910740803

  日期：1991.12.11

  gel, is used for the preparative separation by recycling chromatography of the enantiomers of oxazolidinones rac-5, thioxolanone rac-6, per-hydropyrimidinone rac-7, and dioxinones rac-9 and 10 derived from the acids listed in the title (Figs. 1–5). The oxazolidinones rac-1a, -2, and -4 show a peculiar peak of the separation efficiences upon lowering the Chiraspher-column temperature to 15° (Fig. 6). In

  Chiraspher，乙基的聚合物Ñ上球形硅胶-acryloylphenylalanine，是通过回收恶唑烷酮的对映体的色谱法用于制备分离外消旋- 5，thioxolanone外消旋- 6，每hydropyrimidinone外消旋- 7，和dioxinones外消旋- 9和10从在标题（列出的酸衍生的图。1 - 5）。恶唑烷酮rac - 1a，-2和-4在降低显示分离efficiences的特有峰Chiraspher -column温度至15°（图。6）。在某些情况下，因此可以制备数克量的对映体纯的杂环。分配了大多数对映异构体的绝对构型。所述的第一应用叔丁基-5-氧代-2-苯基唑烷-3-羧酸乙酯（5），其为亲核手性甘氨酸积木描述（制品13 - 16，方案2）。列出了对映体纯的1,3-二恶英酮（表1），表明它们的绝对构型，旋光度和在Chiraspher上的洗脱行为之间具有相关性。
• Silica gel-promoted new one-pot procedure for the synthesis of 1,3-oxathiolan-5-one
  作者：Manoj P. Thakare、Rahimullah Shaikh、Dipak Tayade

  DOI：10.1080/17415993.2017.1313256

  日期：2017.9.3

  gel-promoted synthesis of 1,3-oxathiolan-5-one derivatives in N,N-Dimethylformamide (DMF) is presented. The reaction was carried out using aromatic aldehyde and mercaptoacetic acid in the presence of silica gel in DMF with heating. The reactions were worked up by separating the silica gel and recovering the solid product after adding water in excellent yields without any chromatographic purification. Structures

  摘要提出了一种高选择性双组分硅胶促进 1,3-oxathiolan-5-one 衍生物在 N,N-二甲基甲酰胺 (DMF) 中的合成。在硅胶存在下，在DMF中加热，使用芳醛和巯基乙酸进行反应。通过分离硅胶并在加水后以极好的收率回收固体产物来处理反应，无需任何色谱纯化。化合物的结构通过1H NMR和LCMS光谱分析得到令人满意的证实。图形概要
• Cobalt doped ZnS nanoparticles as a recyclable catalyst for solvent-free synthesis of heterocyclic privileged medicinal scaffolds under infrared irradiation
  作者：Anshu Dandia、Vijay Parewa、Shyam L. Gupta、Kuldeep S. Rathore

  DOI：10.1016/j.molcata.2013.02.010

  日期：2013.7

  This paper reports preparation and characterization of cobalt doped ZnS NPs and their catalytic application in the synthesis of heterocyclic privileged medicinal scaffolds involving pyrazolones (with excellent regioselectivity) and 1,3-oxathiolan-5-one frameworks under infrared irradiation. Nanoparticles have been prepared at room temperature by a wet chemical method. The heterogeneous catalysts were fully characterized by XRD, TEM, EDAX, ICP-AES and UV/Vis. Under infrared radiation (IR), the catalytic activity of Co doped ZnS NPs was about 40-fold higher under IR as compared to the conventional method. Nanocatalyst plays a dual role of catalyst as well as susceptor, and enhances the overall capacity to absorb IR in the reaction mixture. Doping by Co promotes the activity and selectivity of ZnS NPs as indicated by their high TOF value, providing the products with good to excellent yields. The surface acidity of NPs was measured by FTIR spectra of chemisorbed pyridine. The present method does not involve any hazardous organic solvent or catalyst. The introduction of nanocatalyst in an IR system offers promising features for the reaction response such as the shorter reaction time, simple work-up procedure, and purification of products by non-chromatographic methods. The catalyst was reused up to four runs without an appreciable loss of catalytic activity. (C) 2013 Elsevier B.V. All rights reserved.
• Molecular iodine in [bmim][BF4]: a highly efficient green catalytic system for one-pot synthesis of 1,3-oxathiolan-5-one
  作者：Manika Dewan、Ajeet Kumar、Amit Saxena、Arnab De、Subho Mozumdar

  DOI：10.1016/j.tetlet.2010.09.052

  日期：2010.11

  Aldehydes and mercaptoacetic acid are coupled in the presence of a catalytic amount of economical and non-toxic molecular iodine in [bmim][BF4] ionic liquid under mild conditions to afford the corresponding 1,3-oxathiolan-5-one in excellent yields. Molecular iodine acts faster in ionic liquids when compared to conventional solvents such as DMSO, DMF, ethyl acetate, and acetonitrile. The recovered ionic liquids can be recycled in subsequent reactions with consistent activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Electrolytic Partial Fluorination of Organic Compounds. 30.¹ Drastic Improvement of Anodic Monofluorination of 2-Substituted 1,3-Oxathiolan-5-ones Using the Novel Fluorine Source Et₄NF·4HF
  作者：Seiichiro Higashiya、Satoru Narizuka、Akinori Konno、Tomoko Maeda、Kunitaka Momota、Toshio Fuchigami

  DOI：10.1021/jo981437g

  日期：1999.1.1

  The highly regioselective anodic monofluorination of 2-substituted 1,3-oxathiolan-5-ones was successfully carried out using a novel supporting electrolyte, Et4NF . 4HF, while use of a conventional supporting electrolyte, Et3N . 3HF, resulted in no formation or extremely low yields of the fluorinated products.