(2R,3S)-tetrahydro-5,5-dimethyl-2-phenyl-3-(phenylthio)-2H-pyran | 1334150-04-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R,3S)-tetrahydro-5,5-dimethyl-2-phenyl-3-(phenylthio)-2H-pyran
• 英文别名: (2R,3S)-5,5-dimethyl-2-phenyl-3-phenylsulfanyloxane
• CAS: 1334150-04-7
• 化学式: C₁₉H₂₂OS
• 分子量: 298.449
• InChiKey: SHCBMDHJGHXSRE-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  N-(苯硫基)邻苯二甲酰亚胺 、 2,2-dimethyl-5-phenyl-pent-4-en-1-ol 在 甲烷磺酸 、 (R)-4-(azepan-1-yl)-3,5-dimethyl-4,5-dihydro-3H-dinaphtho[2,1-d:1',2'-f][1,3,2]diazaphosphepine-4-selenide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2S,3R)-tetrahydro-5,5-dimethyl-2-phenyl-3-(phenylthio)-2H-pyran 、 (2R,3S)-tetrahydro-5,5-dimethyl-2-phenyl-3-(phenylthio)-2H-pyran
  参考文献：
  名称：

  Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes

  摘要：

  Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.

  DOI：

  10.1021/ja2064395

文献信息

• Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes
  作者：Scott E. Denmark、David J. P. Kornfilt、Thomas Vogler

  DOI：10.1021/ja2064395

  日期：2011.10.5

  Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.