dimethyl 6-methyl-3,6-dihydro-2H-thiopyran-2,2-dicarboxylate | 1054547-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: dimethyl 6-methyl-3,6-dihydro-2H-thiopyran-2,2-dicarboxylate
• CAS: 1054547-28-2
• 化学式: C₁₀H₁₄O₄S
• 分子量: 230.285
• InChiKey: FKBDOWUJHATHFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  反-1,3-戊二烯 、 溴丙二酸二甲酯 在 sulfur 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以44%的产率得到dimethyl 3-methyl-3,6-dihydro-2H-thiopyran-2,2-dicarboxylate
  参考文献：
  名称：

  Mechanism and Regioselectivity of the Cycloaddition of Thiones Derived from Meldrum’s Acid, Malonates, or Other Dicarbonyls

  摘要：

  [GRAPHICS]Several alpha,alpha-dioxothiones were generated in situ and reacted with 1,3-dienes of varying electronic and steric properties. It was found that thiones 10a and 11a reacted well with electron-rich or electron-poor dienes and are complementary in their regioselectivities when steric effects are at play. The calculated preferred mechanistic pathway implies a thiiranium zwitterion intermediate.

  DOI：

  10.1021/jo800945y

文献信息

• Mechanism and Regioselectivity of the Cycloaddition of Thiones Derived from Meldrum’s Acid, Malonates, or Other Dicarbonyls
  作者：Stéphane Perreault、Maude Poirier、Pascal Léveillé、Olivier René、Pascal Joly、Yves Dory、Claude Spino

  DOI：10.1021/jo800945y

  日期：2008.10.3

  [GRAPHICS]Several alpha,alpha-dioxothiones were generated in situ and reacted with 1,3-dienes of varying electronic and steric properties. It was found that thiones 10a and 11a reacted well with electron-rich or electron-poor dienes and are complementary in their regioselectivities when steric effects are at play. The calculated preferred mechanistic pathway implies a thiiranium zwitterion intermediate.