ethyl (1'R,4'S)-2-(4'-hydroxy-4'-methyl-2'-cyclopenten-1'-yl)-3-oxobutanoate | 926920-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (1'R,4'S)-2-(4'-hydroxy-4'-methyl-2'-cyclopenten-1'-yl)-3-oxobutanoate
• 英文别名: ethyl 2-[(1R,4S)-4-hydroxy-4-methylcyclopent-2-en-1-yl]-3-oxobutanoate
• CAS: 926920-66-3
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: OHTREVWGNLECAH-VXFCFVAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1'R,4'S)-2-(4'-hydroxy-4'-methyl-2'-cyclopenten-1'-yl)-3-oxobutanoate 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)-4-(ethoxycarbonyl)-3,7-dimethyl-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：

  4-Cyclopentene-1,3-diol, 1-methyl-, (1S,3R)- 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'-methyl-2'-cyclopenten-1'-yl)-3-oxobutanoate
  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

文献信息

• Pd(0) catalyzed intramolecular alkylation: stereoselective synthesis of furan and isoxazoline-2-oxide analogs
  作者：Pasha M. Khan、Ruizhi Wu、Kirpal S. Bisht

  DOI：10.1016/j.tet.2006.11.066

  日期：2007.1

  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.