adamantyl allyl sulfide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 烯丙基硫化合物
• 英文名称: adamantyl allyl sulfide
• 英文别名: 1-Prop-2-enylsulfanyladamantane
• 化学式: C₁₃H₂₀S
• 分子量: 208.368
• InChiKey: IRHZBMAPGBKJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-金刚烷乙醇 、 3-溴丙烯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以64%的产率得到adamantyl allyl sulfide
  参考文献：
  名称：

  Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides

  摘要：

  The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a-i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C-2-symmetric bis-oxazoline ligand (5a-c). The degree of asymmetric induction ranged from 2.8% for allyl methyl sulfide (2a) to 60% for (1S,2S,5R)-(+)-allyl menthyl sulfide (2d). The enantioselectivity of the reactions was also dependent on the electronic nature of the sulfide; allyl phenyl sulfide (2e) gave a 14% ee, whereas allyl p-methoxyphenyl sulfide (2i) produced only an 8% ee. The stereochemistry of 2d and (1R,2S,5R)-(+)-allyl menthyl sulfide (7) was assigned on the basis of NMR spectroscopic experiments.

  DOI：

  10.1021/jo991842n

文献信息

• Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides
  作者：Douglas W. McMillen、Norbert Varga、Beth Ann Reed、Claudia King

  DOI：10.1021/jo991842n

  日期：2000.4.1

  The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a-i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C-2-symmetric bis-oxazoline ligand (5a-c). The degree of asymmetric induction ranged from 2.8% for allyl methyl sulfide (2a) to 60% for (1S,2S,5R)-(+)-allyl menthyl sulfide (2d). The enantioselectivity of the reactions was also dependent on the electronic nature of the sulfide; allyl phenyl sulfide (2e) gave a 14% ee, whereas allyl p-methoxyphenyl sulfide (2i) produced only an 8% ee. The stereochemistry of 2d and (1R,2S,5R)-(+)-allyl menthyl sulfide (7) was assigned on the basis of NMR spectroscopic experiments.