(S)-N-(1-phenylethyl)-4-chlorobutyrylamide | 450370-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-N-(1-phenylethyl)-4-chlorobutyrylamide
• 英文别名: 4-chloro-N-(1-phenylethyl)butanamide；4-chloro-N-[(1S)-1-phenylethyl]butanamide
• CAS: 450370-35-1
• 化学式: C₁₂H₁₆ClNO
• 分子量: 225.718
• InChiKey: ZFFIXKVPNNWTNS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-phenylethyl)-4-chlorobutyrylamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以91%的产率得到(S)-N-(1'-phenylethyl)-2-pyrrolidinone
  参考文献：
  名称：

  Sugiyama, Shigeo; Morishita, Kenji; Chiba, Mariko, Heterocycles, 2002, vol. 57, # 4, p. 637 - 648

  摘要：

  DOI：
• 作为产物：
  描述：

  1-bromo-4-chloro-1-nitrobutane 、 (S)-(-)- α-甲基苄胺 在 N-碘代丁二酰亚胺 、 氧气 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 24.0h， 以72%的产率得到(S)-N-(1-phenylethyl)-4-chlorobutyrylamide
  参考文献：
  名称：

  Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant

  摘要：

  Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.

  DOI：

  10.1021/ol502089v

文献信息

• Asymmetric Synthesis of 1-Methyl-2-(2-hydroxyethyl)pyrrolidine
  作者：Theo Nikiforov、Stephan Stanchev、Branimir Milenkov、Vladimir Dimitrov

  DOI：10.3987/r-1986-07-1825

  日期：——
• Sugiyama, Shigeo; Morishita, Kenji; Chiba, Mariko, Heterocycles, 2002, vol. 57, # 4, p. 637 - 648
  作者：Sugiyama, Shigeo、Morishita, Kenji、Chiba, Mariko、Ishii, Keitaro

  DOI：——

  日期：——
• Umpolung Amide Synthesis Using Substoichiometric <i>N</i>-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
  作者：Kenneth E. Schwieter、Bo Shen、Jessica P. Shackleford、Matthew W. Leighty、Jeffrey N. Johnston

  DOI：10.1021/ol502089v

  日期：2014.9.19

  Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.