5-(Phenylsulfanyl)-1-oxaspiro[5.5]undecane | 135967-30-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(Phenylsulfanyl)-1-oxaspiro[5.5]undecane
• 英文别名: 5-Phenylsulfanyl-1-oxaspiro[5.5]undecane
• CAS: 135967-30-5
• 化学式: C₁₆H₂₂OS
• 分子量: 262.416
• InChiKey: OBJCDZAUPBUQHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(phenylthio)-1-cyclohexanecarboxaldehyde 在 吡啶 、 盐酸 、 对甲苯磺酸 、 对甲苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 5-(Phenylsulfanyl)-1-oxaspiro[5.5]undecane
  参考文献：
  名称：

  Kinetic and Thermodynamic Control in the Synthesis of Tetrahydro-Pyrans and -Furans from 1,4-Diols by Stereospecific Phenylsulfanyl (PhS) Migration: Competition Between exo and endo Transition States and between [1,2] and [1,4]Sulfanyl Participation

  摘要：

  控制1,4-二醇环化形成THP而非THF的因素进行了重新评估。此外，我们提供了关于[1,2]和[1,4]硫烷参与与环化之间竞争的证据，这一过程涉及到一个五元环状磺基盐。

  DOI：

  10.1055/s-1999-2814

文献信息

• Synthesis of cyclic ethers and allylic sulfides by rearrangement of phenylsulfanyl substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride
  作者：Laurent Djakovitch、Jason Eames、David J. Fox、Francis H. Sansbury、Stuart Warren

  DOI：10.1039/a905498g

  日期：——

  Rearrangement of a series of 1,n-diols (n = 2 to 12), with a PhS-group adjacent to one OH group, under two sets of conditions gives single compounds in excellent yield drawn for four possible classes of products. The effect of the chain length helps in the understanding of the different cyclisation modes and the mechanism of the rearrangements.

   在两组条件下，一系列Phs-基团与一个OH基团相邻的1，n-二醇（n = 2至12）的重排产生了四种化合物，并以极佳的收率得到了单一化合物。链长的影响有助于理解不同的环化模式和重排机制。
• Rearrangements of phenylthio substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride
  作者：Laurent Djakovitch、Jason Eames、Ray V.H. Jones、Sara McIntyre、Stuart Warren

  DOI：10.1016/0040-4039(95)00055-h

  日期：1995.3

  Rearrangement of a series of 1,n diols (n= 2 to 12), one OH group having an adjacent PhS group, under the two sets of conditions in the title, gives single compounds in high yield drawn from four possible classes of product. The effects of chain length help in our understanding of the mechanism of the rearrangements.

  在标题中的两组条件下，将一系列1，n二醇（n = 2至12）（一个OH基团具有一个相邻的PhS基团）进行重排，可以从四种可能的产物类别中以高收率得到单一化合物。链长的影响有助于我们了解重排的机理。
• Synthesis of tetrahydropyrans by hydroxyl participation in phenylthio migration
  作者：Francis H. Sansbury、Stuart Warren

  DOI：10.1016/s0040-4039(00)92726-6

  日期：1991.7

  Acid-catalysed cyclisation of substituted 1,6- or 1,4-alkane diols with suitably placed phenylthio groups leads to high yields of tetrahydropyrans formed by exo or endo hydroxyl participation during phenylthio migration with inversion at both the migration origin and terminus.
• Kinetic and Thermodynamic Control in the Synthesis of Tetrahydro-Pyrans and -Furans from 1,4-Diols by Stereospecific Phenylsulfanyl (PhS) Migration: Competition Between <i>exo</i> and <i>endo</i> Transition States and between [1,2] and [1,4]Sulfanyl Participation
  作者：Jason Eames、Nikolai Kuhnert、Francis H. Sansbury、Stuart Warren

  DOI：10.1055/s-1999-2814

  日期：1999.8

  The factors controlling the cyclisation of 1,4-diols with PhS migration to give THPs rather than THFs are reassessed. Furthermore we provide evidence for a competition between [1,2] and [1,4] sulfanyl participation and cyclisation onto a five membered cyclic sulfonium salt.

  控制1,4-二醇环化形成THP而非THF的因素进行了重新评估。此外，我们提供了关于[1,2]和[1,4]硫烷参与与环化之间竞争的证据，这一过程涉及到一个五元环状磺基盐。