benzyl (4S,5R)-5-methyl-2-(2-phenylmethoxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate | 434953-01-2

• 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: benzyl (4S,5R)-5-methyl-2-(2-phenylmethoxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 434953-01-2
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: ATXJPDJRAWYFBU-JPYJTQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4S,5R)-5-methyl-2-(2-phenylmethoxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以71%的产率得到(4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid
  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：

  在 二乙胺基三氟化硫 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到benzyl (4S,5R)-5-methyl-2-(2-phenylmethoxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
  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

文献信息

• A Latent Oxazoline Electrophile for N−O−C Bond Formation in Pseudomonine Biosynthesis
  作者：Elizabeth S. Sattely、Christopher T. Walsh

  DOI：10.1021/ja804499r

  日期：2008.9.17

  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.