methyl trans-2-phenyl-1,4-oxathiane-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫烷类
• 英文名称: methyl trans-2-phenyl-1,4-oxathiane-3-carboxylate
• 英文别名: methyl (2R,3S)-2-phenyl-1,4-oxathiane-3-carboxylate
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: DPLNIDIXKWUKMM-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-phenyl-1,3-oxathiolane 、 重氮乙酸甲酯 在 rhodium(II) acetate dimer 作用下， 以 苯 为溶剂， 反应 3.0h， 以5%的产率得到(Z)-methyl 3-(2-methoxycarbonylmethylsulfanylethoxy)-3-phenyl-acrylate
  参考文献：
  名称：

  The methoxycarbonylcarbene insertion into 1,3-dithiolane and 1,3-oxathiolane rings

  摘要：

  Treatment of substituted 1,3-dithiolanes and 1,3-oxathiolanes with methyl diazoacetate in the presence of Rh-2(OAC)(4) effects ring expansion to the corresponding substituted 1,4-dithiane-2-carboxylates and 1,4-oxathiane-3-carboxylates. The sulfur ylides initially generated in these reactions undergo Stevens rearrangement in competition with both [2,3]-C-C-sigmatropic rearrangement and intramolecular fraomentation. In the case of 2-styryl-substituted 1,3-oxathiolane and 1,3-dithiolane, fing expansion on one-, three- and fourcarbons subsequently takes place. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.01.100

文献信息

• The methoxycarbonylcarbene insertion into 1,3-dithiolane and 1,3-oxathiolane rings
  作者：Alexander V. Stepakov、Alexander P. Molchanov、Jörg Magull、Denis Vidović、Galina L. Starova、Jürgen Kopf、Rafael R. Kostikov

  DOI：10.1016/j.tet.2006.01.100

  日期：2006.4

  Treatment of substituted 1,3-dithiolanes and 1,3-oxathiolanes with methyl diazoacetate in the presence of Rh-2(OAC)(4) effects ring expansion to the corresponding substituted 1,4-dithiane-2-carboxylates and 1,4-oxathiane-3-carboxylates. The sulfur ylides initially generated in these reactions undergo Stevens rearrangement in competition with both [2,3]-C-C-sigmatropic rearrangement and intramolecular fraomentation. In the case of 2-styryl-substituted 1,3-oxathiolane and 1,3-dithiolane, fing expansion on one-, three- and fourcarbons subsequently takes place. (c) 2006 Elsevier Ltd. All fights reserved.