dimethyl N-sulfinylphoshoramidate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dimethyl N-sulfinylphoshoramidate
• 英文别名: [Methoxy-(sulfinylamino)phosphoryl]oxymethane
• 化学式: C₂H₆NO₄PS
• 分子量: 171.114
• InChiKey: XLGXKDLJZXVHJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二硫代磷酸-O,O-二(1-甲基乙基)酯 、 dimethyl N-sulfinylphoshoramidate 生成 硫代过氧二磷酸四异丙酯
  参考文献：
  名称：

  KUTYREV G. A.; MAVRIN V. YU.; CHERKASOV R. A.; PUDOVIK A. N., IZV. AN CCCP. CEP. XIM., 1980, HO 6, 1402-1404

  摘要：

  DOI：
• 作为产物：
  描述：

  (氨基-甲氧基磷酰)氧基甲烷 在 氯化亚砜 作用下， 以 苯 为溶剂， 以68%的产率得到dimethyl N-sulfinylphoshoramidate
  参考文献：
  名称：

  Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels−Alder Reactions of N-Sulfinylphosphoramidates¹

  摘要：

  The [4 + 2] cycloaddition reactions of N-sulfinvlphosphoramidates, prepared from the corresponding phosphoramidates by treatment with N-(chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10)and presence (>95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.

  DOI：

  10.1021/jo970186t

文献信息

• Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels−Alder Reactions of <i>N</i>-Sulfinylphosphoramidates¹
  作者：Yinsheng Zhang、Christopher J. Flann

  DOI：10.1021/jo970186t

  日期：1998.3.1

  The [4 + 2] cycloaddition reactions of N-sulfinvlphosphoramidates, prepared from the corresponding phosphoramidates by treatment with N-(chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10)and presence (>95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.
• KUTYREV G. A.; MAVRIN V. YU.; CHERKASOV R. A.; PUDOVIK A. N., IZV. AN CCCP. CEP. XIM., 1980, HO 6, 1402-1404
  作者：KUTYREV G. A.、 MAVRIN V. YU.、 CHERKASOV R. A.、 PUDOVIK A. N.

  DOI：——

  日期：——