2-(benzyloxy)-1-(1,2,3,4-tetrahydro-2-hydroxynaphth-2-yl)ethan-1-one | 139719-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(benzyloxy)-1-(1,2,3,4-tetrahydro-2-hydroxynaphth-2-yl)ethan-1-one
• 英文别名: 1-(2-hydroxy-3,4-dihydro-1H-naphthalen-2-yl)-2-phenylmethoxyethanone
• CAS: 139719-65-6
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: YOLBDYRJZQBUMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  β-四氢萘酮 在 盐酸 、 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 甲醇 、 苯 为溶剂， 反应 17.0h， 生成 2-(benzyloxy)-1-(1,2,3,4-tetrahydro-2-hydroxynaphth-2-yl)ethan-1-one
  参考文献：
  名称：

  [2-Benzyloxy)-1-(N-2,6-xylylimino)ethyl]samarium as a synthetic equivalent to .alpha.-hydroxyacetyl anion

  摘要：

  DOI：

  10.1021/ja00162a064

文献信息

• Synthesis of .alpha.-hydroxy ketones by samarium(II) iodide-mediated coupling of organic halides, an isocyanide, and carbonyl compounds
  作者：Masahiro Murakami、Teiji Kawano、Hajime Ito、Yoshihiko Ito

  DOI：10.1021/jo00058a028

  日期：1993.3

  A new strategy for the synthesis of a-hydroxy ketones by samarium(II) iodide-mediated three-component coupling of organic halides, an isocyanide, and carbonyl compounds is disclosed. An (alpha-iminoalkyl)samarium(III) species is generated in situ by treatment of an organic halide with 2 equiv of samarium(II) iodide in the presence of 2,6-xylyl isocyanide. Subsequent treatment of the mixture with a carbonyl compound affords alpha-hydroxy imines, which are converted by acid-catalyzed hydrolysis to the corresponding alpha-hydroxy ketones. The mild reaction conditions employed are compatible with a variety of functionalities including terminal acetylenes and trimethylsilyl ethers. Application of the method to the synthesis of alpha-hydroxy aldehydes is also presented.