(1S*,2S*,3S*,7S*,8R*)-2,3;7,8-Diepoxycyclodecanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S*,2S*,3S*,7S*,8R*)-2,3;7,8-Diepoxycyclodecanol
• 英文别名: (1R,2S,5R,7S,11S)-6,12-dioxatricyclo[9.1.0.05,7]dodecan-2-ol
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: BQAZUTVYNXESPQ-GENCIFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S*,2S*,3S*,7S*,8R*)-2,3;7,8-Diepoxycyclodecanol 在 titanium(IV) isopropylate 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到(1R*,2R*,3S*,6R*,7R*)-7-Iodo-11-oxabicyclo<4.4.1>undecane-2,3-diol
  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：

  (1Z,6Z)-环癸-1,6-二烯 在 copper(I) chloride 叔丁基过氧化氢 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 异辛烷 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 (1S*,2S*,3S*,7S*,8R*)-2,3;7,8-Diepoxycyclodecanol
  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