(1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monoisopropyl ester | 201815-23-8

• 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: (1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monoisopropyl ester
• CAS: 201815-23-8
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: YKOGKWGGMISKRS-UYXSQOIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monoisopropyl ester 在 盐酸 、 三乙基硼氢化锂 作用下， 生成 (1S,2R,6R,7R)-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-one
  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：

  exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 反应 144.0h， 以63%的产率得到(1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monoisopropyl ester
  参考文献：
  名称：

  Seebach, Dieter; Jaeschke, Georg; Wang, Yan Ming, Angewandte Chemie, 1995, vol. 107, # 21, p. 2605 - 2606

  摘要：

  DOI：