S-(2,6-dimethylphenyl) (1S)-1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carbothioate | 1407512-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-(2,6-dimethylphenyl) (1S)-1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carbothioate
• CAS: 1407512-45-1
• 化学式: C₁₅H₁₆O₄S
• 分子量: 292.356
• InChiKey: VJMVAZBOWBQCMO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 S-(2,6-dimethylphenyl) (1S)-1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carbothioate 在 silver trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到(1R)-1-羟基-4-甲氧基-2-氧代环戊-3-烯-1-羧酸甲酯
  参考文献：
  名称：

  Catalytic Enantioselective O-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds

  摘要：

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.

  DOI：

  10.1021/ja309311z
• 作为产物：
  描述：

  S-(2,6-dimethylphenyl) (1S)-4-methoxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]oxy-2-oxocyclopent-3-ene-1-carbothioate 在 molybdenum hexacarbonyl 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以87%的产率得到S-(2,6-dimethylphenyl) (1S)-1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carbothioate
  参考文献：
  名称：

  Catalytic Enantioselective O-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds

  摘要：

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.

  DOI：

  10.1021/ja309311z

文献信息

• Catalytic Enantioselective <i>O</i>-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds
  作者：Mahiuddin Baidya、Kimberly A. Griffin、Hisashi Yamamoto

  DOI：10.1021/ja309311z

  日期：2012.11.14

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.