4-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)butyl acetate | 14739-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)butyl acetate
• 英文别名: 4-(2,2-Dimethyl-1,3-dioxolan-4-yl)butyl acetate
• CAS: 14739-13-0
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: FLMXMCDJRRHMHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)butyl acetate 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.0h， 以96%的产率得到4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034
• 作为产物：
  描述：

  5-烯己酯 在 四氧化锇 、 camphor-10-sulfonic acid 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.25h， 生成 4-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)butyl acetate
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034

文献信息

• Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations
  作者：Lana M. Grubb、Katherine A. Brown、Bruce P. Branchaud

  DOI：10.1016/s0040-4039(98)00601-7

  日期：1998.5

  reported on the cyclization of (ω-hydroxy-β-hydroxyalkyl)cobaloximes (1, 2 and 3) to form 5, 6 and 7-membered ring cyclic ethers (4, 5 and 6). Reversible cyclization and eventual irreversible alkene decomplexation (to form 7, 8 and 9) varied as a function of ring size. The practical consequence is that cyclizations to form 5 and 6 membered rings are feasible whereas formation of a 7 membered ring is not.

  关于（ω-羟基-β-羟基烷基）钴肟（1、2和3）的环化以形成5、6和7元环醚（4、5和6）的研究已有报道。可逆环化和最终不可逆烯烃分解（形成7、8和9）随环大小的变化而变化。实际的结果是形成5和6元环的环化是可行的，而形成7元环的环化是不可行的。