(S)-5-(2-(2-bromophenyl)-2-(4-methoxyphenylthio)ethyl)-3-methyl-4-nitroisoxazole | 1334145-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-5-(2-(2-bromophenyl)-2-(4-methoxyphenylthio)ethyl)-3-methyl-4-nitroisoxazole
• 英文别名: 5-[(2S)-2-(2-bromophenyl)-2-(4-methoxyphenyl)sulfanylethyl]-3-methyl-4-nitro-1,2-oxazole
• CAS: 1334145-83-3
• 化学式: C₁₉H₁₇BrN₂O₄S
• 分子量: 449.325
• InChiKey: CHEVFVPPJUKHLV-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5-(2-(2-bromophenyl)-2-(4-methoxyphenylthio)ethyl)-3-methyl-4-nitroisoxazole 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以80%的产率得到(-)-5-(2-(2-bromophenyl)-2-(4-methoxyphenylthio)ethyl)-3-methylisoxazol-4-amine
  参考文献：
  名称：

  Catalytic Asymmetric 1,6-Michael Addition of Arylthiols to 3-Methyl-4-nitro-5-alkenyl-isoxazoles with Bifunctional Catalysts

  摘要：

  An enantioselective 1,6-Michael addition reaction of arylthiols to a wide range of 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by readily available Takemoto's thiourea catalyst has been developed. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds bearing a 4-nitroisoxazol-5-yl moiety in high to excellent yields (up to 97%) and high enantioselectivities (up to 91% ee). Significantly, the potential utilities of the protocol had been further demonstrated by gram-scale reaction and the versatile conversions of some resulting products into other functionalized and useful compounds.

  DOI：

  10.1021/jo2012779
• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 (E)-5-(2-bromostyryl)-3-methyl-4-nitroisoxazole 在 1-[3,5-双(三氟甲基)苯基]-3-[(1R,2R)-(-)-2-(二甲氨基)环己基]硫脲 作用下， 以 氯苯 为溶剂， 反应 45.5h， 以93%的产率得到(S)-5-(2-(2-bromophenyl)-2-(4-methoxyphenylthio)ethyl)-3-methyl-4-nitroisoxazole
  参考文献：
  名称：

  Catalytic Asymmetric 1,6-Michael Addition of Arylthiols to 3-Methyl-4-nitro-5-alkenyl-isoxazoles with Bifunctional Catalysts

  摘要：

  An enantioselective 1,6-Michael addition reaction of arylthiols to a wide range of 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by readily available Takemoto's thiourea catalyst has been developed. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds bearing a 4-nitroisoxazol-5-yl moiety in high to excellent yields (up to 97%) and high enantioselectivities (up to 91% ee). Significantly, the potential utilities of the protocol had been further demonstrated by gram-scale reaction and the versatile conversions of some resulting products into other functionalized and useful compounds.

  DOI：

  10.1021/jo2012779