4-O-butyl 1-O-ethyl but-2-enedioate | 7397-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-O-butyl 1-O-ethyl but-2-enedioate
• CAS: 7397-58-2
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: FGGPJCOTXDEUMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 4-hydroxy-2-butenyl carbonate 、 正丁醇 在 manganese(IV) oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-甲氧基-3-硝基三氟甲苯 作用下， 以85%的产率得到4-O-butyl 1-O-ethyl but-2-enedioate
  参考文献：
  名称：

  N-Heterocyclic carbene-catalyzed oxidations

  摘要：

  N-Hererocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized,, protected carboxylates. The oxidation proceeds Under mild conditions, with low loadings of including a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.

  DOI：

  10.1016/j.tet.2008.10.033

文献信息

• N-Heterocyclic carbene-catalyzed oxidations
  作者：Brooks E. Maki、Audrey Chan、Eric M. Phillips、Karl A. Scheidt

  DOI：10.1016/j.tet.2008.10.033

  日期：2009.4

  N-Hererocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized,, protected carboxylates. The oxidation proceeds Under mild conditions, with low loadings of including a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.