N-sulfinyl-2-oxo-5,5-dimethyl-1,3,2-dioxazaphosphoramidate | 203111-76-6

• 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: N-sulfinyl-2-oxo-5,5-dimethyl-1,3,2-dioxazaphosphoramidate
• 英文别名: 5,5-Dimethyl-2-(sulfinylamino)-1,3,2lambda5-dioxaphosphinane 2-oxide；5,5-dimethyl-2-(sulfinylamino)-1,3,2λ5-dioxaphosphinane 2-oxide
• CAS: 203111-76-6
• 化学式: C₅H₁₀NO₄PS
• 分子量: 211.178
• InChiKey: KCNFZRUIZCGJMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• 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：

  N-sulfinyl-2-oxo-5,5-dimethyl-1,3,2-dioxazaphosphoramidate 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-cyclohex-3-en-1-yl-5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-amine
  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
• 作为产物：
  描述：

  5,5-二甲基-2-氯-1,3,2-二氧磷杂己内酰磷酸酯 在 氨 、 N-(chlorosulfinyl)imidazole 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 N-sulfinyl-2-oxo-5,5-dimethyl-1,3,2-dioxazaphosphoramidate
  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.