S-((4,4-diacetyl-1-methyl-2-methylenecyclopentyl)methyl)ethanethioate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: S-((4,4-diacetyl-1-methyl-2-methylenecyclopentyl)methyl)ethanethioate
• 英文别名: S-[(4,4-diacetyl-1-methyl-2-methylidenecyclopentyl)methyl] ethanethioate
• 化学式: C₁₄H₂₀O₃S
• 分子量: 268.377
• InChiKey: WRWQCPNGTVLREE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(2-methylallyl)-3-(prop-2-yn-1-yl)pentane-2,4-dione 、 硫代乙酸 在 Au-Pd nanoparticles supported on TiO₂ 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 S-((4,4-diacetyl-1-methyl-2-methylenecyclopentyl)methyl)ethanethioate
  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

• Novel radical tandem 1,6-enynes thioacylation/cyclization: Au–Pd nanoparticles catalysis versus thermal activation as a function of the substrate specificity
  作者：Irene Notar Francesco、Justine Giauffret、Fabien Fontaine-Vive、Jennifer K. Edwards、Christopher J. Kiely、Graham J. Hutchings、Sylvain Antoniotti

  DOI：10.1016/j.tet.2014.10.077

  日期：2014.12

  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.