4-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-methyl-2-phenyl-1,3-oxathiolan-5-one | 1367367-74-5

• 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: 4-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-methyl-2-phenyl-1,3-oxathiolan-5-one
• CAS: 1367367-74-5
• 化学式: C₁₈H₁₇ClO₃S
• 分子量: 348.85
• InChiKey: LFPMFTIFFVAKOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-methyl-2-phenyl-1,3-oxathiolan-5-one 在 水 作用下， 生成 (3S,5S)-5-(4-chlorophenyl)-3-sulfanyloxolan-2-one
  参考文献：
  名称：

  Efficient Ce(III)-Catalyzed cis-Selective Synthetic Approach to γ-Lactones in Aqueous Media

  摘要：

  The first CeCl3 center dot 7H(2)O-catalyzed, one-pot synthesis of alpha-mercapto-gamma-lactones via regioselective epoxide ring opening and mercaptoacetylative cyclization cascades in water is reported. The reaction between 2-methyl-2-phenyl-1,3-oxathiolan-5-one and a variety of terminal epoxides was carried out in aqueous media to afford gamma-lactones in good to excellent yields (83-94%) with complete cis diastereoselectivity. Acetophenone obtained as a by-product was also recovered and recycled easily for further use.

  DOI：

  10.1080/00397911.2010.540923
• 作为产物：
  描述：

  苯乙酮 在 cerium(III) chloride heptahydrate 、 水 、 lithium bromide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-methyl-2-phenyl-1,3-oxathiolan-5-one
  参考文献：
  名称：

  Efficient Ce(III)-Catalyzed cis-Selective Synthetic Approach to γ-Lactones in Aqueous Media

  摘要：

  The first CeCl3 center dot 7H(2)O-catalyzed, one-pot synthesis of alpha-mercapto-gamma-lactones via regioselective epoxide ring opening and mercaptoacetylative cyclization cascades in water is reported. The reaction between 2-methyl-2-phenyl-1,3-oxathiolan-5-one and a variety of terminal epoxides was carried out in aqueous media to afford gamma-lactones in good to excellent yields (83-94%) with complete cis diastereoselectivity. Acetophenone obtained as a by-product was also recovered and recycled easily for further use.

  DOI：

  10.1080/00397911.2010.540923

文献信息

• Epoxides to α-Mercapto-γ-lactones via Ionic Liquid Promoted Mercaptoacetylative Ring-Opening-Ring-Closing Cascade
  作者：Lal Yadav、Rajesh Patel、Vishnu Srivastava

  DOI：10.1055/s-0030-1258121

  日期：2010.7

  Task-specific ionic liquid promoted [Bmim]OH} one-pot synthesis of α-mercapto-γ-lactones is reported. The present protocol involves regioselective epoxide ring opening and intramolecular translactonisation cascade. A variety of epoxides undergo this ring-opening-ring-closing cascade with 2-methyl-2-phenyl-1,3-­oxathiolan-5-one to afford α-mercapto-γ-lactones diastereoselectively in good to excellent yields. After isolation of the product, the ionic liquid [Bmim]OH could be easily recovered and reused without any loss of efficiency.

  报告了特定任务离子液体促进[Bmim]OH}一锅合成δ-巯基δ-内酯的过程。本方案涉及区域选择性环氧化物开环和分子内转内酯化级联反应。多种环氧化物与 2-甲基-2-苯基-1,3-氧硫杂环戊-5-酮发生这种开环-闭环级联反应，以良好至极佳的收率非对映选择性地得到±-巯基δ-δ-内酯。分离出产物后，离子液体 [Bmim]OH 可以很容易地回收和重复使用，而不会降低效率。