N^ε-cinnamoyl-N^ε-(benzoyloxy)-N^α-BOC-L-lysine methyl ester | 145385-46-2

• 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^ε-cinnamoyl-N^ε-(benzoyloxy)-N^α-BOC-L-lysine methyl ester
• 英文别名: [[(5S)-6-methoxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohexyl]-[(E)-3-phenylprop-2-enoyl]amino] benzoate
• CAS: 145385-46-2
• 化学式: C₂₈H₃₄N₂O₇
• 分子量: 510.587
• InChiKey: ZKOBMLNLTURFNQ-AWXSUDRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N^ε-cinnamoyl-N^ε-(benzoyloxy)-N^α-BOC-L-lysine methyl ester 在 氨 作用下， 反应 2.83h， 以93%的产率得到N^ε-cinnamoyl-N^ε-hydroxy-N^α-BOC-L-lysine methyl ester
  参考文献：
  名称：

  The total synthesis of nannochelin: a novel cinnamoyl hydroxamate-containing siderophore

  摘要：

  The total synthesis of nannochelin A, a siderophore isolated from Nannocystis exedens, is described. The key transformation involves the tandem oxidation-acylation of the N(epsilon)-amino group of N(alpha)-BOC-L-lysine methyl ester prior to coupling with the external carboxyls of citric acid.

  DOI：

  10.1021/jo00052a030
• 作为产物：
  描述：

  N-α-(tert-butoxycarbonyl)-L-lysine methyl ester 、 过氧化苯甲酰 在 sodium carbonate 、 3-苯基-2-丙烯酰氯 作用下， 生成 N^ε-benzoyl-N^α-BOC-L-lysine methyl ester 、 N^ε-cinnamoyl-N^ε-(benzoyloxy)-N^α-BOC-L-lysine methyl ester
  参考文献：
  名称：

  The total synthesis of nannochelin: a novel cinnamoyl hydroxamate-containing siderophore

  摘要：

  The total synthesis of nannochelin A, a siderophore isolated from Nannocystis exedens, is described. The key transformation involves the tandem oxidation-acylation of the N(epsilon)-amino group of N(alpha)-BOC-L-lysine methyl ester prior to coupling with the external carboxyls of citric acid.

  DOI：

  10.1021/jo00052a030

文献信息

• The total synthesis of nannochelin: a novel cinnamoyl hydroxamate-containing siderophore
  作者：Raymond J. Bergeron、Otto Phanstiel

  DOI：10.1021/jo00052a030

  日期：1992.12

  The total synthesis of nannochelin A, a siderophore isolated from Nannocystis exedens, is described. The key transformation involves the tandem oxidation-acylation of the N(epsilon)-amino group of N(alpha)-BOC-L-lysine methyl ester prior to coupling with the external carboxyls of citric acid.