dimethyl 3,3-dimethyl-4-(phenylsulfanylmethylene)cyclopentane-1,1-dicarboxylate | 1164274-77-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 3,3-dimethyl-4-(phenylsulfanylmethylene)cyclopentane-1,1-dicarboxylate
• CAS: 1164274-77-4
• 化学式: C₁₈H₂₂O₄S
• 分子量: 334.436
• InChiKey: MVGRUWYJDCGKQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  苯硫酚 、 dimethyl methallylpropargylmalonate 在 Au-Pd nanoparticles supported on TiO₂ 作用下， 以 乙腈 为溶剂， 生成 dimethyl 3-methyl-5-(phenylsulfanylmethylene)cyclohexane-1,1-dicarboxylate 、 dimethyl 3,3-dimethyl-4-(phenylsulfanylmethylene)cyclopentane-1,1-dicarboxylate
  参考文献：
  名称：

  Novel radical tandem 1,6-enynes thioacylation/cyclization: Au–Pd nanoparticles catalysis versus thermal activation as a function of the substrate specificity

  摘要：

  We studied the reactivity of 1,6-enynes with thioacetic acid (AcSH) under either thermal conditions or in the presence of catalytic amounts of supported Au or Au-Pd nanoparticles (NPs) under mild conditions. The 1,6-enynes undergo a tandem thioacylation/cyclization to original cyclic products featuring either a homoallylic thioester function or an enol thioester function depending on the substrate topology. Interestingly, the former process was found more efficient when performed in the presence of Au-Pd NPs while the latter process can be efficiently carried out under thermal conditions (100 degrees C). The reaction proceeds by a radical mechanism and the presence of precious metal NPs seems to stabilize the formation of free radical intermediates, as supported by experimental and theoretical results. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.077

文献信息

• Reductive Addition of the Benzenethiyl Radical to Alkynes by Amine-Mediated Single Electron Transfer Reaction to Diphenyl Disulfide
  作者：Tsuyoshi Taniguchi、Tatsuya Fujii、Atsushi Idota、Hiroyuki Ishibashi

  DOI：10.1021/ol901084k

  日期：2009.8.6

  Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compounds are also presented.

  炔烃的氢硫基化与二苯基二硫化物和三丙胺一起进行。可以提出胺介导的单电子转移到二苯二硫的反应机理。还介绍了该方法在烯炔化合物自由基环化中的应用。