(R)-4-[(phenylthio)methyl]-2-(2-spiroadamantyl)-1,3-dioxolane | 675957-36-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-4-[(phenylthio)methyl]-2-(2-spiroadamantyl)-1,3-dioxolane
• 英文别名: (4R)-4-(phenylsulfanylmethyl)spiro[1,3-dioxolane-2,2'-adamantane]
• CAS: 675957-36-5
• 化学式: C₁₉H₂₄O₂S
• 分子量: 316.464
• InChiKey: RIWHNZDWLHPODV-CMPFZWEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-[(phenylthio)methyl]-2-(2-spiroadamantyl)-1,3-dioxolane 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以22%的产率得到(R)-4-[fluoro(phenylthio)methyl]-2-(2-spiroadamantyl)-1,3-dioxolane
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds.71.¹ Highly Diastereoselective Anodic Fluorination of Sulfides Having Oxygen-Containing Heterocyclic Groups

  摘要：

  Diastereoselective anodic fluorination of sulfides having various oxygen-containing heterocyclic substituents such as 2-furanyl, 1,3-dioxolanyl, 2,2-dimethyl-1,3-dioxolanyl, 2-spirocyclohexyl-1,3-dioxolanyl, 2-spiroadamantyl-1,3-dixolanyl, and 1,3-dioxolanonyl groups at the beta-position was comparatively studied. Among the oxygen-containing heterocyclic substituents, the 2-spirocyclohexyl-1,3-dioxolanyl group gave the best diastereoselectivity (80% de). The diastereoselectivity was also affected by supporting fluoride salts and solvents. Chemical fluorination using selectfluor resulted in much lower diastereoselectivity and extremely poor yield. The fluorinated products were readily converted into the corresponding fluorinated diol in good yields by acidic hydrolysis.

  DOI：

  10.1021/jo035291j
• 作为产物：
  描述：

  2,2-二甲氧基金刚烷 、 (2R)-3-(phenylthio)-1,2-propanediol 在 对甲苯磺酸 作用下， 生成 (R)-4-[(phenylthio)methyl]-2-(2-spiroadamantyl)-1,3-dioxolane
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds.71.¹ Highly Diastereoselective Anodic Fluorination of Sulfides Having Oxygen-Containing Heterocyclic Groups

  摘要：

  Diastereoselective anodic fluorination of sulfides having various oxygen-containing heterocyclic substituents such as 2-furanyl, 1,3-dioxolanyl, 2,2-dimethyl-1,3-dioxolanyl, 2-spirocyclohexyl-1,3-dioxolanyl, 2-spiroadamantyl-1,3-dixolanyl, and 1,3-dioxolanonyl groups at the beta-position was comparatively studied. Among the oxygen-containing heterocyclic substituents, the 2-spirocyclohexyl-1,3-dioxolanyl group gave the best diastereoselectivity (80% de). The diastereoselectivity was also affected by supporting fluoride salts and solvents. Chemical fluorination using selectfluor resulted in much lower diastereoselectivity and extremely poor yield. The fluorinated products were readily converted into the corresponding fluorinated diol in good yields by acidic hydrolysis.

  DOI：

  10.1021/jo035291j

文献信息

• Electrolytic Partial Fluorination of Organic Compounds.71.¹ Highly Diastereoselective Anodic Fluorination of Sulfides Having Oxygen-Containing Heterocyclic Groups
  作者：Katsutoshi Suzuki、Toshio Fuchigami

  DOI：10.1021/jo035291j

  日期：2004.2.1

  Diastereoselective anodic fluorination of sulfides having various oxygen-containing heterocyclic substituents such as 2-furanyl, 1,3-dioxolanyl, 2,2-dimethyl-1,3-dioxolanyl, 2-spirocyclohexyl-1,3-dioxolanyl, 2-spiroadamantyl-1,3-dixolanyl, and 1,3-dioxolanonyl groups at the beta-position was comparatively studied. Among the oxygen-containing heterocyclic substituents, the 2-spirocyclohexyl-1,3-dioxolanyl group gave the best diastereoselectivity (80% de). The diastereoselectivity was also affected by supporting fluoride salts and solvents. Chemical fluorination using selectfluor resulted in much lower diastereoselectivity and extremely poor yield. The fluorinated products were readily converted into the corresponding fluorinated diol in good yields by acidic hydrolysis.