Dimethyl <(tert-butoxycarbonyl)amino><(phenylthio)methyl>malonate | 153180-13-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Dimethyl <(tert-butoxycarbonyl)amino><(phenylthio)methyl>malonate
• 英文别名: dimethyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylsulfanylmethyl)propanedioate
• CAS: 153180-13-3
• 化学式: C₁₇H₂₃NO₆S
• 分子量: 369.439
• InChiKey: OTFMUNRXUMJWDN-UHFFFAOYSA-N

物化性质

• 沸点：
  497.0±45.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Dimethyl <(tert-butoxycarbonyl)amino><(phenylthio)methyl>malonate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Dimethyl <<4-<(tert-butoxycarbonyl)amino>butyryl>amino><(phenylthio)methyl>malonate
  参考文献：
  名称：

  Dimethyl amino[(phenylthio)methyl]malonate: a useful C-3 unit in a mild, direct synthesis of oxazole-4-carboxylates

  摘要：

  N-Acyl derivatives of the title compound undergo oxidative cyclization upon treatment with N-chlorosuccinimide in DMF to form dimethyl 4,5-dihydro(phenylthio)oxazole-4,4-dicarboxylates 4 which then are decarbomethoxylated with concomitant loss of thiophenoxide to form 2-substituted-4-carbomethoxy-5-unsubstituted oxazoles 1. The mildness and generality of this method has been demonstrated by the synthesis of a variety of examples, including a fragment used for a synthesis of calyculin A.

  DOI：

  10.1021/jo00073a040
• 作为产物：
  描述：

  二乙基(Boc-氨基)乙酯 在 四丁基溴化铵 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Dimethyl <(tert-butoxycarbonyl)amino><(phenylthio)methyl>malonate
  参考文献：
  名称：

  Dimethyl amino[(phenylthio)methyl]malonate: a useful C-3 unit in a mild, direct synthesis of oxazole-4-carboxylates

  摘要：

  N-Acyl derivatives of the title compound undergo oxidative cyclization upon treatment with N-chlorosuccinimide in DMF to form dimethyl 4,5-dihydro(phenylthio)oxazole-4,4-dicarboxylates 4 which then are decarbomethoxylated with concomitant loss of thiophenoxide to form 2-substituted-4-carbomethoxy-5-unsubstituted oxazoles 1. The mildness and generality of this method has been demonstrated by the synthesis of a variety of examples, including a fragment used for a synthesis of calyculin A.

  DOI：

  10.1021/jo00073a040