Acetic acid (1S,4R)-4-(1-benzenesulfonyl-2-oxo-2-phenyl-ethyl)-1-trimethylsilanylethynyl-cyclopent-2-enyl ester | 934976-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1S,4R)-4-(1-benzenesulfonyl-2-oxo-2-phenyl-ethyl)-1-trimethylsilanylethynyl-cyclopent-2-enyl ester
• 英文别名: [(1S,4R)-4-[1-(benzenesulfonyl)-2-oxo-2-phenylethyl]-1-(2-trimethylsilylethynyl)cyclopent-2-en-1-yl] acetate
• CAS: 934976-74-6
• 化学式: C₂₆H₂₈O₅SSi
• 分子量: 480.657
• InChiKey: RNEHTCXVDQWMOU-VOUYXJAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,4R)-4-(1-benzenesulfonyl-2-oxo-2-phenyl-ethyl)-1-trimethylsilanylethynyl-cyclopent-2-enyl ester 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以64%的产率得到(1S,5S)-3-phenyl-4-(phenylsulfonyl)-7-trimethylsilanylethynyl-2-oxabicyclo[3.3.0]octa-3,7-diene
  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 18.0h， 生成 Acetic acid (1S,4R)-4-(1-benzenesulfonyl-2-oxo-2-phenyl-ethyl)-1-trimethylsilanylethynyl-cyclopent-2-enyl ester
  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