4-methyl-4-(phenylthio)-3,4-dihydro-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-methyl-4-(phenylthio)-3,4-dihydro-2H-pyran
• 英文别名: 4-Methyl-4-phenylsulfanyl-2,3-dihydropyran
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: PLWSGHARARCINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-4-(phenylthio)-3,4-dihydro-2H-pyran 在 高氯酸 、 双氧水 、 vanadia 作用下， 以 甲醇 、 水 为溶剂， 以47%的产率得到4-甲基-5,6-二氢吡喃-2-酮
  参考文献：
  名称：

  Dihydropyran as a Template for Lactone Synthesis

  摘要：

  3,4-Dihydro-2H-pyran (DHP) was efficiently transformed into 4-thiophenyl-3,4-dihydro-2H-pyran. This intermediate was converted to the corresponding 1,3-O,Sallylic carbanion with t-butyllithium and selectively alkylated at the carbon a to the sulfur with alkyl halides, an epoxide, and an aldehyde. An one-pot oxidative elimination of the sulfur fragment using vanadium pentoxide generates the desired beta-substituted alpha,beta-unsaturated delta-unsaturated-valero lactone.

  DOI：

  10.1080/00397910701557358
• 作为产物：
  描述：

  4-(phenylthio)-3,4-dihydro-2H-pyran 、 碘甲烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 1.5h， 以88%的产率得到4-methyl-4-(phenylthio)-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Dihydropyran as a Template for Lactone Synthesis

  摘要：

  3,4-Dihydro-2H-pyran (DHP) was efficiently transformed into 4-thiophenyl-3,4-dihydro-2H-pyran. This intermediate was converted to the corresponding 1,3-O,Sallylic carbanion with t-butyllithium and selectively alkylated at the carbon a to the sulfur with alkyl halides, an epoxide, and an aldehyde. An one-pot oxidative elimination of the sulfur fragment using vanadium pentoxide generates the desired beta-substituted alpha,beta-unsaturated delta-unsaturated-valero lactone.

  DOI：

  10.1080/00397910701557358

文献信息

• Dihydropyran as a Template for Lactone Synthesis
  作者：Matthew P. Brichacek、Robert M. Carlson

  DOI：10.1080/00397910701557358

  日期：2007.10.1

  3,4-Dihydro-2H-pyran (DHP) was efficiently transformed into 4-thiophenyl-3,4-dihydro-2H-pyran. This intermediate was converted to the corresponding 1,3-O,Sallylic carbanion with t-butyllithium and selectively alkylated at the carbon a to the sulfur with alkyl halides, an epoxide, and an aldehyde. An one-pot oxidative elimination of the sulfur fragment using vanadium pentoxide generates the desired beta-substituted alpha,beta-unsaturated delta-unsaturated-valero lactone.