(1S,2R,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid monoisopropyl ester | 173541-02-1

• 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: (1S,2R,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid monoisopropyl ester
• 英文别名: (1R,2S,3R,4S)-3-propan-2-yloxycarbonylbicyclo[2.2.2]oct-5-ene-2-carboxylic acid
• CAS: 173541-02-1
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: QDHWBASRYOMROR-ZRUFSTJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (1S,2R,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid monoisopropyl ester 在 磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 (1S,2R,3S,4R)-3-((S)-1-Phenyl-ethylcarbamoyl)-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid isopropyl ester
  参考文献：
  名称：

  Highly Enantioselective Ring Opening of Cyclic Meso-Anhydrides to Isopropyl Hemiesters with Ti−TADDOLates:  An Alternative to Hydrolytic Enzymes?

  摘要：

  The Lewis acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLate (1) to cyclic meso anhydrides to afford the corresponding hemiesters is described. By using this method a variety of structurally different anhydrides can be converted to isopropyl hemiesters with high enantioselectivities (enantiomer ratios up to 99:1). We have also investigated Lewis acidic titanium complexes, which differ from 1 in the chiral ligand or the alkoxide ligand that is transferred. Finally, a catalytic version, which allows the substoichiometric use of Ti-TADDOLate in the presence of stoichiometric amounts of Al(Oi-Pr)(3), is presented.

  DOI：

  10.1021/jo971731t
• 作为产物：
  描述：

  、 meso-endo-tetrahydro-4,7-ethanoisobenzofuran-1,3-dione 以 乙醚 为溶剂， 反应 120.0h， 生成 (1S,2R,3S,4R)-Bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid monoisopropyl ester
  参考文献：
  名称：

  Highly Enantioselective Ring Opening of Cyclic Meso-Anhydrides to Isopropyl Hemiesters with Ti−TADDOLates:  An Alternative to Hydrolytic Enzymes?

  摘要：

  The Lewis acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLate (1) to cyclic meso anhydrides to afford the corresponding hemiesters is described. By using this method a variety of structurally different anhydrides can be converted to isopropyl hemiesters with high enantioselectivities (enantiomer ratios up to 99:1). We have also investigated Lewis acidic titanium complexes, which differ from 1 in the chiral ligand or the alkoxide ligand that is transferred. Finally, a catalytic version, which allows the substoichiometric use of Ti-TADDOLate in the presence of stoichiometric amounts of Al(Oi-Pr)(3), is presented.

  DOI：

  10.1021/jo971731t

文献信息

• Highly Enantioselective Ring Opening of Cyclic <i>Meso</i>-Anhydrides to Isopropyl Hemiesters with Ti−TADDOLates:  An Alternative to Hydrolytic Enzymes?
  作者：Georg Jaeschke、Dieter Seebach

  DOI：10.1021/jo971731t

  日期：1998.2.1

  The Lewis acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLate (1) to cyclic meso anhydrides to afford the corresponding hemiesters is described. By using this method a variety of structurally different anhydrides can be converted to isopropyl hemiesters with high enantioselectivities (enantiomer ratios up to 99:1). We have also investigated Lewis acidic titanium complexes, which differ from 1 in the chiral ligand or the alkoxide ligand that is transferred. Finally, a catalytic version, which allows the substoichiometric use of Ti-TADDOLate in the presence of stoichiometric amounts of Al(Oi-Pr)(3), is presented.