Acetic acid (1S,2R,6S,7R,8S)-7,8-dihydroxy-11-oxa-bicyclo[4.4.1]undec-2-yl ester | 135158-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Acetic acid (1S,2R,6S,7R,8S)-7,8-dihydroxy-11-oxa-bicyclo[4.4.1]undec-2-yl ester
• CAS: 135158-93-9
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: XWVNNUPHUVQAKR-KZZRWZIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R,6S,7R,8S)-7,8-dihydroxy-11-oxa-bicyclo[4.4.1]undec-2-yl ester 在 sodium periodate 、 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 31.0h， 生成 (2R,4aR,6R,9aR)-6-[1,3]Dioxolan-2-yl-2-phenylsulfanyl-octahydro-1,5-dioxa-benzocycloheptene
  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：

  silver(I) acetate 、 (1R*,2R*,3S*,6R*,7R*)-7-Iodo-11-oxabicyclo<4.4.1>undecane-2,3-diol 以 氯仿 、 溶剂黄146 为溶剂， 反应 5.0h， 以83%的产率得到Acetic acid (1S,2R,6S,7R,8S)-7,8-dihydroxy-11-oxa-bicyclo[4.4.1]undec-2-yl ester
  参考文献：
  名称：

  针对微藻聚醚毒素的模型研究。立体选择性进入C 10顺式和反式融合的恶烷-环氧庚烷亚基

  摘要：

  描述了一种新的合成方法，用于从（Z，Z）-cyclodeca-2,7-dien-1-ol开始构建顺式和反式融合的恶烷-环氧庚烷体系。调用Ti（O i Pr）4催化的跨环环氧乙烷装置扩展来解释11-氧代双环[4.4.1]十一烷中间体的化学选择性形成。

  DOI：

  10.1016/s0040-4039(00)79692-4