N-(4-cyano-3-oxo-4-(tetrahydro-1l4-thiophen-1-ylidene)butyl)pivalamide | 1221411-48-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-cyano-3-oxo-4-(tetrahydro-1l4-thiophen-1-ylidene)butyl)pivalamide
• CAS: 1221411-48-8
• 化学式: C₁₄H₂₂N₂O₂S
• 分子量: 282.407
• InChiKey: ZGQXIBXRIKUWBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.96
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-cyano-3-oxo-4-(tetrahydro-1l4-thiophen-1-ylidene)butyl)pivalamide 、 cyclohexanecarbaldoxime 在 Oxone 作用下， 以 四氢呋喃 、 水 、 二氯甲烷 为溶剂， 反应 24.25h， 以59%的产率得到2-cyclohexyl-5-oxo-4-(2-pivalamidoethyl)-2,5-dihydrooxazole 3-oxide
  参考文献：
  名称：

  Chemoselective Protection of α-Ketoacids by Direct Annulations with Oximes

  摘要：

  Oximes and alpha-ketoacids undergo an unexpectedly facile and chemoselective annulation to afford 2,5-dihydrooxazole 3-oxides. The resulting cyclic nitrones serve as chemically and configurationally stable masked a-ketoacids that can be easily elaborated and manipulated. Deprotection is achieved by mild reduction with zinc metal and hydrolysis. This methodology allows for the protection, elaboration, and deprotection of enantiopure peptide derived, a-ketoacids, which are the key starting materials for the chemoselective ketoacid-hydroxylamine peptide ligation.

  DOI：

  10.1021/ol100467t
• 作为产物：
  描述：

  1-(cyanomethyl)tetrahydro-1H-thiophen-1-ium bromide 、 3-[(2,2-二甲基丙酰基)氨基]丙酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 反应 18.0h， 以61%的产率得到N-(4-cyano-3-oxo-4-(tetrahydro-1l4-thiophen-1-ylidene)butyl)pivalamide
  参考文献：
  名称：

  Chemoselective Protection of α-Ketoacids by Direct Annulations with Oximes

  摘要：

  Oximes and alpha-ketoacids undergo an unexpectedly facile and chemoselective annulation to afford 2,5-dihydrooxazole 3-oxides. The resulting cyclic nitrones serve as chemically and configurationally stable masked a-ketoacids that can be easily elaborated and manipulated. Deprotection is achieved by mild reduction with zinc metal and hydrolysis. This methodology allows for the protection, elaboration, and deprotection of enantiopure peptide derived, a-ketoacids, which are the key starting materials for the chemoselective ketoacid-hydroxylamine peptide ligation.

  DOI：

  10.1021/ol100467t