(+/-)-2,2-dimethylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate | 1185060-40-5

• 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: (+/-)-2,2-dimethylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate
• CAS: 1185060-40-5
• 化学式: C₁₅H₂₀N₂O₆S
• 分子量: 356.4
• InChiKey: IIHYHPSDTTYLMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  115.61
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2,2-dimethylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate 在 Pd[1,2-bis(phenylsulfinyl)ethane](OAc)2 、 (meso)-1,2-bis(phenylsulfinyl)ethane 、 苯基-P-苯醌 作用下， 以 四氢呋喃 为溶剂， 以21%的产率得到(+/-)-(4R,5R)-5-tert-butyl-3-(4-nitrophenylsulfonyl)-4-vinyloxazolidin-2-one
  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：

  2,2-二甲基-5-己烯-3-醇 、 4-nitrobenzenesulfonyl isocyanate 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (+/-)-2,2-dimethylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate
  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