(+)-5-(2-(2-chlorophenyl)-2-(phenylsulfonyl)ethyl)-3-methyl-4-nitroisoxazole | 1334145-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-5-(2-(2-chlorophenyl)-2-(phenylsulfonyl)ethyl)-3-methyl-4-nitroisoxazole
• 英文别名: 5-[(2S)-2-(benzenesulfonyl)-2-(2-chlorophenyl)ethyl]-3-methyl-4-nitro-1,2-oxazole
• CAS: 1334145-89-9
• 化学式: C₁₈H₁₅ClN₂O₅S
• 分子量: 406.846
• InChiKey: WFMCJVGWXXRBEB-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-(2-(2-chlorophenyl)-2-(phenylthio)ethyl)-3-methyl-4-nitroisoxazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (-)-5-(2-(2-chlorophenyl)-2-(phenylsulfonyl)ethyl)-3-methyl-4-nitroisoxazole 、 (+)-5-(2-(2-chlorophenyl)-2-(phenylsulfonyl)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