(2'S,2''S,4S,4'S)-2-<2-<2-(Methoxycarbonyl)-4-phenylpentyl>>-4-(2-phenylpropyl)-4-methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide | 132539-84-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (2'S,2''S,4S,4'S)-2-<2-<2-(Methoxycarbonyl)-4-phenylpentyl>>-4-(2-phenylpropyl)-4-methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide
• 英文别名: (2'RS,2''RS,4RS,4'RS)-2-<2-<2-(Methoxycarbonyl)-4-phenylpentyl>>-4-(2-phenylpropyl)-4-methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide；(2'RS,2''RS,4RS,4'RS)-2-{2-[2-(Methoxycarbonyl)-4-phenylpentyl]}-4-(2-phenylpropyl)-4-methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide
• CAS: 132539-84-5；132618-48-5；132618-49-6；132618-50-9；132618-51-0；132618-52-1
• 化学式: C₂₅H₃₂N₂O₅S
• 分子量: 472.605
• InChiKey: JXCHYRHBMHFDDC-PIYXRGFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2RS,2'RS,4RS,4'RS)-N,N'-Bis<2-<2-(methoxycarbonyl)-4-phenylpentyl>>sulfamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(2'S,2''S,4S,4'S)-2-<2-<2-(Methoxycarbonyl)-4-phenylpentyl>>-4-(2-phenylpropyl)-4-methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide
  参考文献：
  名称：

  Synthesis of precursors to model styrene/methyl methacrylate copolymer radicals. .alpha.,.alpha.'-Bis(methoxycarbonyl)azoalkanes

  摘要：

  Several symmetrical alpha,alpha'-bis(methoxycarbonyl)azoalkanes 4 were prepared in high yield in two steps from the appropriate alpha-amino esters 13, or in five steps from 4-substituted 4-phenyl-2-butanones 10. The sequence involves the generation, separation, and purification of symmetrical N,N'-disubstituted sulfamides 14 followed by oxidative rearrangement under modified Ohme-Schmitz-Preuschhof conditions to yield the title compounds. In the absence of the oxidant, the sulfamides are converted quantitatively into 2,4-disubstituted 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides 15. In accord with the above methodology, (4S)-4-phenyl-2-pentanone was transformed into (2R,2'R,4S,4'S)-2,2'-bis(methoxycarbonyl)-4,4'-diphenyl-2,2'-azopentane (4b-Ia), the stereochemistry of which was established from that of its precursor (2R,2'R,4S,4'S)-N,N'-bis[2-[2-(methoxycarbonyl)-4-phenylpentyl]]-sulfamide by single-crystal X-ray analysis.

  DOI：

  10.1021/jo00006a014