2,2,2-Trichloroethyl 5,5-dimethyl-2,2-dioxo-3-oxa-2lambda6-thia-1,4-diazabicyclo[4.1.0]heptane-4-carboxylate | 1310054-30-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 2,2,2-Trichloroethyl 5,5-dimethyl-2,2-dioxo-3-oxa-2lambda6-thia-1,4-diazabicyclo[4.1.0]heptane-4-carboxylate
• 英文别名: 2,2,2-trichloroethyl 5,5-dimethyl-2,2-dioxo-3-oxa-2λ6-thia-1,4-diazabicyclo[4.1.0]heptane-4-carboxylate
• CAS: 1310054-30-8
• 化学式: C₈H₁₁Cl₃N₂O₅S
• 分子量: 353.611
• InChiKey: RXSKGECRWRENTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloroethyl 5,5-dimethyl-2,2-dioxo-3-oxa-2lambda6-thia-1,4-diazabicyclo[4.1.0]heptane-4-carboxylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以84%的产率得到
  参考文献：
  名称：

  Synthesis and Reactivity of Unique Heterocyclic Structures en Route to Substituted Diamines

  摘要：

  Rhodium-catalyzed oxidative cyclization of allylic hydroxylamine-derived sulfamate esters furnishes a novel family of bicyclic aziridines that serve as functional precursors to substituted diamines. Investigations with the N4-Troc form of these heterocycles have led to manifold improvements in reaction performance and scope and have revealed unique differences in the stability and reactivity of such compounds dictated by the choice of N4-protecting group.

  DOI：

  10.1021/ol2010769
• 作为产物：
  描述：

  tert-butyl 2-methylbut-3-en-2-yl carbonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide] 、 碘苯二乙酸 、 magnesium oxide 、 lithium carbonate 作用下， 以 四氢呋喃 、 醋酸异丙酯 为溶剂， 反应 16.0h， 生成 2,2,2-Trichloroethyl 5,5-dimethyl-2,2-dioxo-3-oxa-2lambda6-thia-1,4-diazabicyclo[4.1.0]heptane-4-carboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of Unique Heterocyclic Structures en Route to Substituted Diamines

  摘要：

  Rhodium-catalyzed oxidative cyclization of allylic hydroxylamine-derived sulfamate esters furnishes a novel family of bicyclic aziridines that serve as functional precursors to substituted diamines. Investigations with the N4-Troc form of these heterocycles have led to manifold improvements in reaction performance and scope and have revealed unique differences in the stability and reactivity of such compounds dictated by the choice of N4-protecting group.

  DOI：

  10.1021/ol2010769

文献信息

• Synthesis and Reactivity of Unique Heterocyclic Structures en Route to Substituted Diamines
  作者：David E. Olson、Autumn Maruniak、Sushant Malhotra、Barry M. Trost、J. Du Bois

  DOI：10.1021/ol2010769

  日期：2011.7.1

  Rhodium-catalyzed oxidative cyclization of allylic hydroxylamine-derived sulfamate esters furnishes a novel family of bicyclic aziridines that serve as functional precursors to substituted diamines. Investigations with the N4-Troc form of these heterocycles have led to manifold improvements in reaction performance and scope and have revealed unique differences in the stability and reactivity of such compounds dictated by the choice of N4-protecting group.