(+/-)-methyl 3-(4-nitrophenylsulfonylcarbamoyloxy)hept-6-enoate | 1185060-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-methyl 3-(4-nitrophenylsulfonylcarbamoyloxy)hept-6-enoate
• CAS: 1185060-04-1
• 化学式: C₁₅H₁₈N₂O₈S
• 分子量: 386.383
• InChiKey: AVGPTRJSOZJIFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141.91
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl 3-(4-nitrophenylsulfonylcarbamoyloxy)hept-6-enoate 在 Pd[1,2-bis(phenylsulfinyl)ethane](OAc)2 、 (meso)-1,2-bis(phenylsulfinyl)ethane 、 氧气 、 苯基-P-苯醌 、 对硝基苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以50%的产率得到(+/-)-methyl 2-((4R,6S)-3-(4-nitrophenylsulfonyl)-2-oxo-4-vinyl-1,3-oxazinan-6-yl)acetate
  参考文献：
  名称：

  Allylic C−H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs

  摘要：

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

  DOI：

  10.1021/ja9054959
• 作为产物：
  描述：

  4-nitrobenzenesulfonyl isocyanate 、 methyl 3-hydroxy-6-heptenoate 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (+/-)-methyl 3-(4-nitrophenylsulfonylcarbamoyloxy)hept-6-enoate
  参考文献：
  名称：

  Allylic C−H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs

  摘要：

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

  DOI：

  10.1021/ja9054959