cyclobutane-1,2-dicarboxylic acid mono-i-propyl ester

• 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: cyclobutane-1,2-dicarboxylic acid mono-i-propyl ester
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: BHCIARWEVLAOPB-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cyclobutane-1,2-dicarboxylic acid mono-i-propyl ester 在 盐酸 、 三乙基硼氢化锂 作用下， 生成 (+)-(1S,5R)-3-oxabicyclo<3,2,0>heptan-2-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：

  cis-1,2-cyclobutane dicarboxylic anhydride 、 异丙醇 在 C₄₁H₂₁F₁₂N₂O₂PS 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以91%的产率得到cyclobutane-1,2-dicarboxylic acid mono-i-propyl ester
  参考文献：
  名称：

  双功能布朗斯台德酸/碱有机催化的新结构主题。

  摘要：

  自然合成的：酸/碱催化剂（小号） - 1可在高度对映选择性alcoholytic desymmetrizations使用内消旋酸酐。例如，环丁烷酸酐衍生物2的甲醇化反应可在99：1 er的条件下生成半酯3（参见方案）。酯3用于（+）-格兰迪索的短对映选择性合成。

  DOI：

  10.1002/anie.201000637

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.
• A New Structural Motif for Bifunctional Brønsted Acid/Base Organocatalysis
  作者：Vijay N. Wakchaure、Benjamin List

  DOI：10.1002/anie.201000637

  日期：2010.6.1

  Naturally synthetic: Acid/base catalyst (S)‐1 can be used in highly enantioselective alcoholytic desymmetrizations of meso anhydrides. For example, the methanolysis of cyclobutane anhydride derivative 2 gave hemiester 3 in 99:1 e.r. (see scheme). Ester 3 was used in a short enantioselective synthesis of (+)‐grandisol.

  自然合成的：酸/碱催化剂（小号） - 1可在高度对映选择性alcoholytic desymmetrizations使用内消旋酸酐。例如，环丁烷酸酐衍生物2的甲醇化反应可在99：1 er的条件下生成半酯3（参见方案）。酯3用于（+）-格兰迪索的短对映选择性合成。