tert-butyl (3R)-3-ethyl-2-oxooxolane-3-carboxylate | 1566606-47-0

• 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: tert-butyl (3R)-3-ethyl-2-oxooxolane-3-carboxylate
• CAS: 1566606-47-0
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: QQDBDFSUDJZZGR-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  丙二酸二叔丁酯 在 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 72.0h， 生成 tert-butyl (3R)-3-ethyl-2-oxooxolane-3-carboxylate
  参考文献：
  名称：

  Enantioselective Desymmetrization of Diesters

  摘要：

  The desymmetrization of prochiral diesters with a chiral phosphoric acid catalyst to produce highly enantioenriched lactones in excellent yield is reported. The process is easily scaled and accommodates a variety of substitution patterns, many of which result in the generation of an enantioenriched all-carbon quaternary center. Manipulation of lactone product to useful small building blocks is also described.

  DOI：

  10.1021/jo402853v

文献信息

• Enantioselective Synthesis of α,α-Disubstituted Lactones via a Chiral Brønsted Acid Catalyzed Intramolecular Cyclization
  作者：Jennifer Wilent

  DOI：10.15227/orgsyn.093.0075

  日期：——
• Enantioselective Desymmetrization of Diesters
  作者：Jennifer Wilent、Kimberly S. Petersen

  DOI：10.1021/jo402853v

  日期：2014.3.7

  The desymmetrization of prochiral diesters with a chiral phosphoric acid catalyst to produce highly enantioenriched lactones in excellent yield is reported. The process is easily scaled and accommodates a variety of substitution patterns, many of which result in the generation of an enantioenriched all-carbon quaternary center. Manipulation of lactone product to useful small building blocks is also described.