benzyl 4-methylenetetrahydrofuran-2-carboxylate | 1256845-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-methylenetetrahydrofuran-2-carboxylate
• 英文别名: benzyl (2R)-4-methylideneoxolane-2-carboxylate
• CAS: 1256845-31-4
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: YNIXNUFBMKHUNL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl 2-diazo-4-(hydroxymethyl)pent-4-enoate 在 (CuOTf)*toluene 、 C₃₁H₃₈N₂O₂ 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到benzyl 4-methylenetetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Enantioselective Copper-Catalyzed Intramolecular O−H Insertion: An Efficient Approach to Chiral 2-Carboxy Cyclic Ethers

  摘要：

  A copper-catalyzed asymmetric intramolecular O-H insertion of omega-hydroxy-alpha-diazoesters has been accomplished by using chiral spiro bisoxazoline ligands. This highly enantioselective intramolecular O-H insertion reaction provides an efficient approach to a variety of synthetically important chiral 2-carboxy cyclic ethers with different ring sizes as well as substitution patterns.

  DOI：

  10.1021/ja1078464

文献信息

• Enantioselective Copper-Catalyzed Intramolecular O−H Insertion: An Efficient Approach to Chiral 2-Carboxy Cyclic Ethers
  作者：Shou-Fei Zhu、Xiao-Guang Song、Yu Li、Yan Cai、Qi-Lin Zhou

  DOI：10.1021/ja1078464

  日期：2010.11.24

  A copper-catalyzed asymmetric intramolecular O-H insertion of omega-hydroxy-alpha-diazoesters has been accomplished by using chiral spiro bisoxazoline ligands. This highly enantioselective intramolecular O-H insertion reaction provides an efficient approach to a variety of synthetically important chiral 2-carboxy cyclic ethers with different ring sizes as well as substitution patterns.