Dimethyl amino<(phenylthio)methyl>malonate | 153180-29-1

• 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 amino<(phenylthio)methyl>malonate
• 英文别名: Dimethyl 2-amino-2-(phenylsulfanylmethyl)propanedioate
• CAS: 153180-29-1
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: RSRUWAZLLSSJOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  372.2±42.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl amino<(phenylthio)methyl>malonate 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 dimethyl 2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-5-phenylsulfanyl-5H-1,3-oxazole-4,4-dicarboxylate
  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：

  氯甲基苯硫醚 在 四丁基溴化铵 sodium methylate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 Dimethyl 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

文献信息

• A Flexible Synthetic Approach to the Hennoxazoles
  作者：James Leahy、Eric Zylstra、Miles She、Walter Salamant

  DOI：10.1055/s-2007-967978

  日期：——

  Three advanced intermediates corresponding to the carbon skeleton of the hennoxazoles have been prepared. Central to the strategy is the synthesis of the oxazoles prior to coupling with the other fragments and a dithiane addition to allow for the generation of diastereomers of the natural product.

  已经合成了三个与氮杂环的碳骨架相应的高级中间体。该策略的核心是在与其他片段偶联之前合成氧杂环，并进行二硫杂烷的加成，以产生天然产物的非对映体。