3-(3-Butenylthio)propan-1-ol | 143144-49-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(3-Butenylthio)propan-1-ol
• 英文别名: 3-But-3-enylsulfanylpropan-1-ol
• CAS: 143144-49-4
• 化学式: C₇H₁₄OS
• 分子量: 146.254
• InChiKey: BFNQMKXSSMVEKY-UHFFFAOYSA-N

物化性质

• 沸点：
  212.6±23.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-Butenylthio)propan-1-ol 在 六甲基磷酰三胺 、 sodium hydride 作用下， 反应 0.5h， 生成 3-Butenyl 3-(ethylthio)propyl sulfide
  参考文献：
  名称：

  Studies on the use of bidentate ligands in the directed Pauson-Khand reaction

  摘要：

  The use of bidentate ligands in the directed Pauson-Khand reaction was investigated. Substrates with a three-carbon linkage between the two heteroatoms gave better results than substrates containing two-carbon tethers. Higher yields and better regioselectivities were observed with thioamines and bisthioethers compared to diamines. Overall, only a few bidentate substrates showed marked improvements over previous results obtained with analogous monodentate compounds. Rationalizations based on the possible modes of cycloaddition operative for the various substrates studied are presented.

  DOI：

  10.1021/jo00045a021
• 作为产物：
  描述：

  3-巯基-1-丙醇 、 4-methanesulfonyloxy-1-butene 在 六甲基磷酰三胺 、 sodium hydride 作用下， 生成 3-(3-Butenylthio)propan-1-ol
  参考文献：
  名称：

  Studies on the use of bidentate ligands in the directed Pauson-Khand reaction

  摘要：

  The use of bidentate ligands in the directed Pauson-Khand reaction was investigated. Substrates with a three-carbon linkage between the two heteroatoms gave better results than substrates containing two-carbon tethers. Higher yields and better regioselectivities were observed with thioamines and bisthioethers compared to diamines. Overall, only a few bidentate substrates showed marked improvements over previous results obtained with analogous monodentate compounds. Rationalizations based on the possible modes of cycloaddition operative for the various substrates studied are presented.

  DOI：

  10.1021/jo00045a021

文献信息

• Carbamate as an accelerating group in intermolecular Pauson-Khand reaction
  作者：Shota Asano、Kaori Itto-Nakama、Hirokazu Arimoto

  DOI：10.1016/j.tetlet.2020.151974

  日期：2020.6

  The Pauson-Khand reaction (PKR) is a powerful means for the construction of cyclopentenones. However, its applications have been limited to the intramolecular version of this reaction because poor yield and regioselectivity are often the major problems in intermolecular PKR. Here we describe that a carbamate moiety in alkene substrate accelerates this intermolecular PKR. The reaction of N-4-dimethylaminophenyl

  Pauson-Khand反应（PKR）是构建环戊烯酮的有力手段。然而，由于不良的产率和区域选择性通常是分子间PKR的主要问题，其应用仅限于该反应的分子内形式。在这里，我们描述了烯烃底物中的氨基甲酸酯部分会加速这种分子间PKR。N -4-二甲基氨基苯基O-烯丙基氨基甲酸酯与炔-钴配合物的反应以高产率（高达90％）和区域选择性（＞ 9∶1）得到环戊烯酮。
• Studies on the use of bidentate ligands in the directed Pauson-Khand reaction
  作者：Marie E. Krafft、Carmelinda A. Juliano

  DOI：10.1021/jo00045a021

  日期：1992.9

  The use of bidentate ligands in the directed Pauson-Khand reaction was investigated. Substrates with a three-carbon linkage between the two heteroatoms gave better results than substrates containing two-carbon tethers. Higher yields and better regioselectivities were observed with thioamines and bisthioethers compared to diamines. Overall, only a few bidentate substrates showed marked improvements over previous results obtained with analogous monodentate compounds. Rationalizations based on the possible modes of cycloaddition operative for the various substrates studied are presented.