(E)-1-phenyl-3,5-bis(phenylthio)pent-4-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-phenyl-3,5-bis(phenylthio)pent-4-en-1-one
• 英文别名: (E)-1-phenyl-3,5-bis(phenylsulfanyl)pent-4-en-1-one
• 化学式: C₂₃H₂₀OS₂
• 分子量: 376.543
• InChiKey: RJORFKPGHXIOKK-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-chloro-1-(phenylthio)prop-1-ene 在 氢氧化钾 、 TSMOTf 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 (E)-1-phenyl-3,5-bis(phenylthio)pent-4-en-1-one
  参考文献：
  名称：

  Allylation with Pummerer-generated substituted vinylthionium ions

  摘要：

  Pummerer-derived substituted vinylthionium ions (allyl phenyl sulfoxide, TMSOFf, EtN(i-Pr)(2), CH2Cl2, -78 degrees C) with a beta-trimethylsilylmethyl (2), gamma-phenyl (14), or gamma-phenylthio (15) group allylate the enol silyl ethers of acetophenone (3) and cyclohexanone (4) in good yield. Allylation with (14) and (15) required slow addition of base in order to limit the rate of production of intermediate, and thus avoid unwanted sila-Pummerer type products. Hunig's base conjugate addition was not observed in these cases. Both the (E)- and (Z)- forms of allyl sulfoxide (15) were shown to equilibrate to the (E)-transoid conformer prior to allylation resulting in exclusive (E)-vinyl sulfide formation. Blocking of the gamma-position resulted in preferential alpha- attack.

  DOI：

  10.1016/s0040-4020(01)85513-7

文献信息

• Allylation with substituted vinylthionium ions from SnCl4 ionisation of 1,3- and 3,3-bis(alkyl/phenylthio) propenes
  作者：Roger Hunter、Joseph P. Michael、Daryl S. Walter

  DOI：10.1016/s0040-4020(01)85514-9

  日期：——

  α- and γ-substituted vinylthionium ions from SnCl4 ionisation of a range of substituted 1,3- and 3,3-bis (alkyl/phenylthio) propenes allylate enol allyl ethers in good yield. Levels of regioselectivity are sterically dependent and in the case of methyl as γ-substituent may be controlled by the steric bulk of the sulfur substituent. As with the Pummerer methodology, γ-addition generally gave (E)-vinyl

  SnCl 4中的α和γ取代的乙烯基硫鎓离子一系列取代的1，3-和3，3-双（烷基/苯硫基）丙烯进行电离，可以高收率烯丙基烯醇烯丙基醚。区域选择性的水平是空间依赖性的，并且在甲基作为γ-取代基的情况下，可以通过硫取代基的空间体积来控制。与Pummerer方法一样，γ加成通常会生成（E）-乙烯基硫化物，专门暗示“游离”乙烯基硫鎓离子的中间体。在适当的情况下，可以将烯丙基化产物水解并环化为罗宾逊环化产物，脱硫为烯烃或消除为二烯。烯丙基三甲基硅烷和吲哚也以高收率被烯丙基化。具有γ-苯硫基或甲氧基的乙烯基硫鎓离子也经历反应。4。提出了机械原理。该研究以五次硝化序列结束，该序列涉及分子内捕获由该方法产生的乙烯基硫鎓离子。
• Regioselective allylation of enol silyl ethers with γ-heterosubstituted vinylthionium ions
  作者：Roger Hunter、Joseph P. Michael、Daryl S. Walter

  DOI：10.1016/s0040-4039(00)73530-1

  日期：1994.7

  γ-Heterosubstituted vinylthionium ions regioselectively and diastereoselectively allylate enol silyl ethers. Intramolecular capture of a vinylthionium ion is used as a key step of a novel pentannulation sequence.

  γ-杂取代的乙烯基硫鎓离子区域选择性和非对映选择性地烯丙基化烯醇甲硅烷基醚。乙烯基硫鎓离子的分子内捕获被用作新的戊烯醛化序列的关键步骤。
• Hunter Roger, Michael Joseph P., Walter Daryl S., Tetrahedron Lett, 35 (1994) N 30, S 5481-5484
  作者：Hunter Roger, Michael Joseph P., Walter Daryl S.

  DOI：——

  日期：——
• Michael Joseph P., Simon Clive D., Walter Daryl S., Hunter Roger, Tetrahedron, 50 (1994) N 31, S 9365-9376
  作者：Michael Joseph P., Simon Clive D., Walter Daryl S., Hunter Roger

  DOI：——

  日期：——