1-(tert-Butyldimethylsiloxy)-1-(phenylthio)ethene | 136629-03-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(tert-Butyldimethylsiloxy)-1-(phenylthio)ethene
• 英文别名: Tert-butyl-dimethyl-(1-phenylsulfanylethenoxy)silane
• CAS: 136629-03-3
• 化学式: C₁₄H₂₂OSSi
• 分子量: 266.48
• InChiKey: ITLLLKXKCSDJHA-UHFFFAOYSA-N

物化性质

• 沸点：
  303.6±34.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-1-环丙醇 、 1-(tert-Butyldimethylsiloxy)-1-(phenylthio)ethene 在 manganese(III) tris(2-pyridinecarboxylate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到S-phenyl 5-oxo-5-phenylpentanethioate
  参考文献：
  名称：

  环丙醇衍生物用 2-吡啶羧酸锰 (III) 氧化生成 β-羰基自由基及其与富电子和缺电子烯烃的反应

  摘要：

  通过使用锰 (III) 2-吡啶羧酸盐 (Mn(pic)3)，从环丙醇衍生物氧化生成各种 β-羰基自由基。这些 β-羰基自由基与富电子烯烃如共轭甲硅烷基烯醇醚、乙烯酮硫缩醛、乙烯酮二硫缩醛和乙烯基醚发生分子间反应，以良好的产率得到交叉加成产物。此外，Mn(pic)3和三丁基氢化锡的组合使用使得这些β-羰基与缺电子烯烃如丙烯腈、丙烯醛、丙烯酸甲酯、甲基乙烯基酮和甲基乙烯基酮的1:1加成反应成为可能。 N,N-二甲基丙烯酰胺和相应的产物以中等至良好的收率获得。

  DOI：

  10.1246/bcsj.66.819

文献信息

• Generation of Alkyl Radicals from 1-Oxidoalkylidenechromium(0) Complexes by Oxidation with Manganese(III) 2-Pyridinecarboxylate and Their Reactions with Olefins
  作者：Koichi Narasaka、Hidehiro Sakurai

  DOI：10.1246/cl.1993.1269

  日期：1993.7

  Tetramethylammonium pentacarbonyl(1-oxidoalkylidene)chromium(0) complexes, prepared from the corresponding carbanion and hexacarbonylchromium(0), are oxidized with manganese(III) 2-pyridinecarboxylate to generate carbon-centered radicals which react with various olefins giving the intermolecular addition products.

  由相应的碳负离子和六羰基铬 (0) 制备的四甲基铵五羰基 (1-氧化亚烷基) 铬 (0) 配合物与 2-吡啶羧酸锰 (III) 氧化生成以碳为中心的自由基，该自由基与各​​种烯烃反应生成分子间加成产物.
• Total synthesis of (-)-tetrahydrolipstatin
  作者：Stephen Hanessian、Ashok Tehim、Ping Chen

  DOI：10.1021/jo00079a022

  日期：1993.12

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.
• Iwasawa, Nobuharu; Hayakawa, Satoshi; Isobe, Koichi, Chemistry Letters, 1991, p. 1193 - 1196
  作者：Iwasawa, Nobuharu、Hayakawa, Satoshi、Isobe, Koichi、Narasaka, Koichi

  DOI：——

  日期：——
• Generation of<i>β</i>-Carbonyl Radicals from Cyclopropanol Derivatives by the Oxidation with Manganese(III) 2-Pyridinecarboxylate and Their Reactions with Electron-Rich and -Deficient Olefins
  作者：Nobuharu Iwasawa、Satoshi Hayakawa、Masahiro Funahashi、Koichi Isobe、Koichi Narasaka

  DOI：10.1246/bcsj.66.819

  日期：1993.3

  Various β-carbonyl radicals are generated oxidatively from cyclopropanol derivatives by the use of manganese(III) 2-pyridinecarboxylate (Mn(pic)3). These β-carbonyl radicals react with electron-rich olefins such as conjugated silyl enol ethers, a ketene thioacetal, a ketene dithioacetal, and a vinyl ether intermolecularly to give crossed-addition products in good yield. Furthermore, the combined use

  通过使用锰 (III) 2-吡啶羧酸盐 (Mn(pic)3)，从环丙醇衍生物氧化生成各种 β-羰基自由基。这些 β-羰基自由基与富电子烯烃如共轭甲硅烷基烯醇醚、乙烯酮硫缩醛、乙烯酮二硫缩醛和乙烯基醚发生分子间反应，以良好的产率得到交叉加成产物。此外，Mn(pic)3和三丁基氢化锡的组合使用使得这些β-羰基与缺电子烯烃如丙烯腈、丙烯醛、丙烯酸甲酯、甲基乙烯基酮和甲基乙烯基酮的1:1加成反应成为可能。 N,N-二甲基丙烯酰胺和相应的产物以中等至良好的收率获得。