2-[5-(chloromethyl)-1,3-oxathiolan-2-ylidene]-1-(4-chlorophenyl)ethanone | 1621393-89-2

• 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-[5-(chloromethyl)-1,3-oxathiolan-2-ylidene]-1-(4-chlorophenyl)ethanone
• 英文别名: (2Z)-2-[5-(chloromethyl)-1,3-oxathiolan-2-ylidene]-1-(4-chlorophenyl)ethanone
• CAS: 1621393-89-2
• 化学式: C₁₂H₁₀Cl₂O₂S
• 分子量: 289.182
• InChiKey: RLOZQGNUEAPUTO-XGICHPGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate 、 环氧氯丙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 以80%的产率得到2-[5-(chloromethyl)-1,3-oxathiolan-2-ylidene]-1-(4-chlorophenyl)ethanone
  参考文献：
  名称：

  Regioselectivity in the Ring Opening of Epoxides: A Metal-Free Cascade C–S/C–O Bond Formation Approach to 1,3-Oxathiolan-2-ylidenes through Heteroannulation of α-Enolic Dithioesters at Room Temperature

  摘要：

  An operationally simple and efficient approach to hitherto unreported and synthetically demanding 1,3-oxathiolan-2-ylidenes has been developed. The approach involves a cascade [2+3] heteroannulation of alpha-enolic dithioesters with epoxides promoted by non-nucleophilic moderate base Cs2CO3 at room temperature. Typical features of this strategy include metal-free mild reaction conditions, atom-economy, high yields, and efficacy of forming two consecutive C-S and C-O bonds, and one ring in a single stroke. MeSH is the only by-product, and the stereochemistry of the exocyclic alpha-oxoketene moiety of 1,3-oxathiolane was assigned to have Z-configuration.

  DOI：

  10.1055/s-0033-1341086