4-phenylthio-2-phenyltetrahydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-phenylthio-2-phenyltetrahydro-2H-pyran
• 英文别名: (2R,4S)-2-phenyl-4-phenylsulfanyloxane
• 化学式: C₁₇H₁₈OS
• 分子量: 270.395
• InChiKey: TWYUUHSTXDPVFN-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  3-丁烯-1-醇 、 苯甲醛 、 苯硫酚 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到4-phenylthio-2-phenyltetrahydro-2H-pyran
  参考文献：
  名称：

  Three-component synthesis of 2-aryl-4-arylthio-tetrahydro-2H-pyrans via the Prins-cyclization

  摘要：

  A three-component coupling of aldehyde, homoallylic alcohol and aryl thiol, has been achieved in the presence of trifluoroacetic acid in dichloromethane at room temperature to produce 4-arylthiotetrahydropyrans in good yields with all cis-selectivity. This method is simple, selective and convenient for introducing a thiol group on a tetrahydropyran ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.176

文献信息

• An Efficient Prins Cyclization for Stereoselective Synthesis of Tetrahydropyran from Imines and Homoallyl Alcohols
  作者：Congrong Liu、Daojuan Cheng、Fulai Yang

  DOI：10.1002/cjoc.201400450

  日期：2014.11

  An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth‐promoted Prins cyclization of imines with homoallyl alcohols. In the presence of 40 mol% BiCl3, a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4‐chlorotetrahydropyran derivatives in good to excellent yields.

  已经开发出了一种空前的方案，用于通过铋促进的Prins与高烯丙醇对亚胺的Prins环化反应来高效合成取代的四氢吡喃。在40 mol％BiCl 3的存在下，各种各样的亚胺在室温下与均烯丙基醇平稳反应，以良好的收率得到相应的4-氯四氢吡喃衍生物。
• Three-component synthesis of 2-aryl-4-arylthio-tetrahydro-2H-pyrans via the Prins-cyclization
  作者：J.S. Yadav、B.V. Subba Reddy、Y. Jayasudhan Reddy、N. Sivasankar Reddy

  DOI：10.1016/j.tetlet.2009.03.176

  日期：2009.6

  A three-component coupling of aldehyde, homoallylic alcohol and aryl thiol, has been achieved in the presence of trifluoroacetic acid in dichloromethane at room temperature to produce 4-arylthiotetrahydropyrans in good yields with all cis-selectivity. This method is simple, selective and convenient for introducing a thiol group on a tetrahydropyran ring. (C) 2009 Elsevier Ltd. All rights reserved.