(Z)-methyl 3-(2-methoxycarbonylmethylsulfanylethylsulfanyl)-3-phenyl-acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 3-(2-methoxycarbonylmethylsulfanylethylsulfanyl)-3-phenyl-acrylate
• 英文别名: methyl (Z)-3-[2-(2-methoxy-2-oxoethyl)sulfanylethylsulfanyl]-3-phenylprop-2-enoate
• 化学式: C₁₅H₁₈O₄S₂
• 分子量: 326.438
• InChiKey: ZPPLONGTJWIRFP-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 3-(2-methoxycarbonylmethylsulfanylethylsulfanyl)-3-phenyl-acrylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以87%的产率得到(Z)-3-(2-carboxymethylsulfanyl-ethylsulfanyl)-3-phenyl-acrylic acid
  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
• 作为产物：
  描述：

  苯甲醛乙烷-1,2-二基二硫代缩醛 、 重氮乙酸甲酯 在 rhodium(II) acetate dimer 作用下， 以 苯 为溶剂， 反应 2.75h， 以31%的产率得到methyl cis-3-phenyl-1,4-dithiane-2-carboxylate
  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.