[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl-[(E)-oct-2-enoyl]amino] benzoate | 198217-02-6

• 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: [3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl-[(E)-oct-2-enoyl]amino] benzoate
• CAS: 198217-02-6
• 化学式: C₂₃H₃₄N₂O₅
• 分子量: 418.533
• InChiKey: NHEURAYNMVBYIT-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl-[(E)-oct-2-enoyl]amino] benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以89%的产率得到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
• 作为产物：
  描述：

  2-辛烯酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 [3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl-[(E)-oct-2-enoyl]amino] benzoate
  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

• An Improved Synthesis of <i>O</i>-Benzoyl Protected Hydroxamates
  作者：Queenie Xianghong Wang、Jennifer King、Phanstiel

  DOI：10.1021/jo971126q

  日期：1997.11.1

  Several primary amines (R-NH2) were converted to their corresponding O-benzoyl protected hydroxamates under biphasic conditions. The intermediate (benzoyloxy)amines (R-NHOCOPh) were generated using benzoyl peroxide dissolved in CH2Cl2 and an aqueous carbonate buffer (pH 10.5) at room temperature. Subsequent acylation with R'COCl gave the protected hydroxamates (R'CONROCOPh) in good overall yields (56-89%).
• 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.