(2-nitro-4-(2-oxoethyl)-1H-pyrrol-1-yl)methyl benzoate | 1514894-19-9

• 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: (2-nitro-4-(2-oxoethyl)-1H-pyrrol-1-yl)methyl benzoate
• 英文别名: [2-Nitro-4-(2-oxoethyl)pyrrol-1-yl]methyl benzoate；[2-nitro-4-(2-oxoethyl)pyrrol-1-yl]methyl benzoate
• CAS: 1514894-19-9
• 化学式: C₁₄H₁₂N₂O₅
• 分子量: 288.26
• InChiKey: LTZDASGZJDMPQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-nitro-4-(2-oxoethyl)-1H-pyrrol-1-yl)methyl benzoate 在 Oxone 、 Shi's ketone 、 sodium tetraborate decahydrate 、 四丁基氟化铵 、 四丁基硫酸氢铵 、 sodium hexamethyldisilazane 、 disodium ethylenediaminetetraacetic acid 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.67h， 生成 (+)-heronapyrrole C
  参考文献：
  名称：

  Total Synthesis of Heronapyrrole C

  摘要：

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.

  DOI：

  10.1021/ol403246j
• 作为产物：
  描述：

  苯甲酸氯甲基 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-碘代丁二酰亚胺 、 硫酸 、 potassium carbonate 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2-nitro-4-(2-oxoethyl)-1H-pyrrol-1-yl)methyl benzoate
  参考文献：
  名称：

  Total Synthesis of Heronapyrrole C

  摘要：

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.

  DOI：

  10.1021/ol403246j

文献信息

• Total Synthesis of Heronapyrrole C
  作者：Xiao-Bo Ding、Daniel P. Furkert、Robert J. Capon、Margaret A. Brimble

  DOI：10.1021/ol403246j

  日期：2014.1.17

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.