tert-butyl-2-(1H-imidazol-4-yl)ethyl(hydroxy)carbamate | 1056311-19-3

• 英文名称: tert-butyl-2-(1H-imidazol-4-yl)ethyl(hydroxy)carbamate
• CAS: 1056311-19-3
• 化学式: C₁₀H₁₇N₃O₃
• 分子量: 227.263
• InChiKey: IOLREQFRAFGTPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.45
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-2-(1H-imidazol-4-yl)ethyl(hydroxy)carbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 0.5h， 以20 mg的产率得到N-hydroxyhistamine bis(trifluoroacetate)
  参考文献：
  名称：

  A Latent Oxazoline Electrophile for N−O−C Bond Formation in Pseudomonine Biosynthesis

  摘要：

  Nitrogen-heteroatom bonds figure prominently in the structural, chemical, and functional diversity of natural products. In the case of Pseudomonas siderophore pseudomonine, an N-O hydroxamate linkage is found uncommonly configured in an isoxazolidinone ring. In an effort to understand the biogenesis of this heterocycle, we have characterized the pseudomonine synthetase in vitro and reconstituted the complete biosynthetic pathway. Our results indicate that the isoxazolidinone of pseudomonine arises from spontaneous rearrangement of an oxazoline precursor. To the best of our knowledge, this is a previously uncharacterized mode of post-assembly line heterocyclization. Our results establish the oxygen of the ubiquitous siderophore hydroxamate functionality as a nucleophile and may be indicative of general strategy for N-O-C bond formation in nature.

  DOI：

  10.1021/ja804499r
• 作为产物：
  描述：

  tert-butyl (2-(1H-imidazol-4-yl)ethyl)(benzyloxy)carbamate 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 tert-butyl-2-(1H-imidazol-4-yl)ethyl(hydroxy)carbamate
  参考文献：
  名称：

  A Latent Oxazoline Electrophile for N−O−C Bond Formation in Pseudomonine Biosynthesis

  摘要：

  Nitrogen-heteroatom bonds figure prominently in the structural, chemical, and functional diversity of natural products. In the case of Pseudomonas siderophore pseudomonine, an N-O hydroxamate linkage is found uncommonly configured in an isoxazolidinone ring. In an effort to understand the biogenesis of this heterocycle, we have characterized the pseudomonine synthetase in vitro and reconstituted the complete biosynthetic pathway. Our results indicate that the isoxazolidinone of pseudomonine arises from spontaneous rearrangement of an oxazoline precursor. To the best of our knowledge, this is a previously uncharacterized mode of post-assembly line heterocyclization. Our results establish the oxygen of the ubiquitous siderophore hydroxamate functionality as a nucleophile and may be indicative of general strategy for N-O-C bond formation in nature.

  DOI：

  10.1021/ja804499r