tert-butyl N-[3-[hydroxy-[(E)-oct-2-enoyl]amino]propyl]carbamate | 202801-94-3

• 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: tert-butyl N-[3-[hydroxy-[(E)-oct-2-enoyl]amino]propyl]carbamate
• CAS: 202801-94-3
• 化学式: C₁₆H₃₀N₂O₄
• 分子量: 314.425
• InChiKey: HHRDCSFHGIRQLZ-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-[hydroxy-[(E)-oct-2-enoyl]amino]propyl]carbamate 在 TEA 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 丁酸,2-羟基-4-[[3-[羟基[(2E)-1-羰基-2-辛烯-1-基]氨基]丙基]氨基]-2-[2-[[3-[羟基[(2E)-1-羰基-2-辛烯-1-基]氨基]丙基]氨基]-2-羰基乙基]-4-羰基-
  参考文献：
  名称：

  Total Synthesis of Acinetoferrin

  摘要：

  The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the N-3-amino group of N-1-BOC propane diamine prior to coupling with the external carboxyls of citric acid. A "one-pot-two-step" reaction converted a primary amine (RNH2) into a O-benzoyl hydroxamate (i.e., RN(OOCPh)COR') in good yield (68%). These studies demonstrated the utility of the O-benzoyl protecting group in the synthesis of alpha,beta-unsaturated hydroxamic acids.

  DOI：

  10.1021/jo9717144
• 作为产物：
  描述：

  1-N-benzoyloxy-3-N-tert-butoxycarbonyl-1,3-diaminopropane 在 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyl N-[3-[hydroxy-[(E)-oct-2-enoyl]amino]propyl]carbamate
  参考文献：
  名称：

  Total Synthesis of Acinetoferrin

  摘要：

  The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the N-3-amino group of N-1-BOC propane diamine prior to coupling with the external carboxyls of citric acid. A "one-pot-two-step" reaction converted a primary amine (RNH2) into a O-benzoyl hydroxamate (i.e., RN(OOCPh)COR') in good yield (68%). These studies demonstrated the utility of the O-benzoyl protecting group in the synthesis of alpha,beta-unsaturated hydroxamic acids.

  DOI：

  10.1021/jo9717144

文献信息

• Total Synthesis of Acinetoferrin
  作者：Queenie Xianghong Wang、Otto Phanstiel

  DOI：10.1021/jo9717144

  日期：1998.3.1

  The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the N-3-amino group of N-1-BOC propane diamine prior to coupling with the external carboxyls of citric acid. A "one-pot-two-step" reaction converted a primary amine (RNH2) into a O-benzoyl hydroxamate (i.e., RN(OOCPh)COR') in good yield (68%). These studies demonstrated the utility of the O-benzoyl protecting group in the synthesis of alpha,beta-unsaturated hydroxamic acids.