(+)-(3S,4S)-4-(benzyloxy)hept-6-en-3-yl 4-nitrophenylsulfonylcarbamate | 1185060-21-2

• 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: (+)-(3S,4S)-4-(benzyloxy)hept-6-en-3-yl 4-nitrophenylsulfonylcarbamate
• CAS: 1185060-21-2
• 化学式: C₂₁H₂₄N₂O₇S
• 分子量: 448.497
• InChiKey: RGKHERJJISMEKZ-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  124.84
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4S)-4-(benzyloxy)hept-6-en-3-yl 4-nitrophenylsulfonylcarbamate 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， 生成 (-)-(4R,5S,6S)-5-(benzyloxy)-6-ethyl-3-(4-nitrophenylsulfonyl)-4-vinyl-1,3-oxazinan-2-one 、 (+/-)-(4S,5S,6S)-5-(benzyloxy)-6-ethyl-3-(4-nitrophenylsulfonyl)-4-vinyl-1,3-oxazinan-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：

  (+)-(3S,4S)-4-(benzyloxy)hept-6-en-3-ol 、 4-nitrobenzenesulfonyl isocyanate 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (+)-(3S,4S)-4-(benzyloxy)hept-6-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