ethyl (1'R,4'S)-2-(4'-hydroxy-4'-trimethylsilanylethynyl-2'-cyclopenten-1'-yl)-2-nitroacetate | 926920-62-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (1'R,4'S)-2-(4'-hydroxy-4'-trimethylsilanylethynyl-2'-cyclopenten-1'-yl)-2-nitroacetate
• CAS: 926920-62-9
• 化学式: C₁₄H₂₁NO₅Si
• 分子量: 311.41
• InChiKey: GQPWXYRICYIMJK-PSIKVXPXSA-N

物化性质

• 沸点：
  388.1±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (1'R,4'S)-2-(4'-hydroxy-4'-trimethylsilanylethynyl-2'-cyclopenten-1'-yl)-2-nitroacetate 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (1S,5S)-3-aza-4-(ethoxycarbonyl)-7-trimethylsilanylethynyl-2-oxabicyclo[3.3.0]octa-3,7-diene-3-oxide
  参考文献：
  名称：

  Pd(0) catalyzed intramolecular alkylation: stereoselective synthesis of furan and isoxazoline-2-oxide analogs

  摘要：

  New optically pure isoxazoline-2-oxide and furan analogs have been synthesized using Pd(0) catalyzed intramolecular cyclizations. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (> 99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereoselective nature of the palladium catalyzed transformations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.066
• 作为产物：
  描述：

  (1S,4R)-1-trimethylsilanylethynyl-cyclopent-2-ene-1,4-diol 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 ethyl (1'R,4'S)-2-(4'-hydroxy-4'-trimethylsilanylethynyl-2'-cyclopenten-1'-yl)-2-nitroacetate
  参考文献：
  名称：

  Pd(0) catalyzed intramolecular alkylation: stereoselective synthesis of furan and isoxazoline-2-oxide analogs

  摘要：

  New optically pure isoxazoline-2-oxide and furan analogs have been synthesized using Pd(0) catalyzed intramolecular cyclizations. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (> 99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereoselective nature of the palladium catalyzed transformations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.066