| 124832-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• CAS: 124832-51-5；132072-56-1；141435-70-3
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: VPPFLMSFSPBWHR-XXMMRNPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 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：
  0.64
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 camphor-10-sulfonic acid 吡啶 、 titanium(IV) isopropylate 、 sodium periodate 、 四氧化锇 、 碘 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 24.0h， 生成 Acetic acid (2S,3S,5R,6S)-5-acetoxy-6-(2-[1,3]dioxolan-2-yl-ethyl)-2-((S)-3-[1,3]dioxolan-2-yl-1-methanesulfonyloxy-propyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Model studies directed towards microalga polyether toxins. A new approach to the construction of trans, syn, trans-oxotricyclic systems

  摘要：

  Investigations into the synthesis of trans,syn,trans-oxotricyclic systems present in marine polyether toxins are described. Present studies have led to the development of a scheme for procuring an appropriately functionalized C12 oxane-oxane-oxepane subunit. A new synthetic process for the construction of beta-dialkoxyoxanes starting from beta-diiodooxolanes has been investigated, demonstrating the ability of heterocyclic oxygens to act as conventional neighbouring group participators towards adjacent electrophilic sites.

  DOI：

  10.1016/s0040-4039(00)79693-6
• 作为产物：
  描述：

  (1S,2R,5Z,9E,12R)-13-oxabicyclo[10.1.0]trideca-5,9-dien-2-ol 生成
  参考文献：
  名称：

  针对微藻聚醚大环内酯类化合物的模型研究：通往12碳四氢呋喃和四氢吡喃亚基的途径

  摘要：

  研究了杂合取代的四氢呋喃和四氢吡喃系统的区域和立体特异性合成的新合成策略，该合成涉及分子内2,3-环氧-环烯醇的碘醚化。可以从X射线研究获得明确的立体化学分配。

  DOI：

  10.1016/s0040-4039(01)80494-9

文献信息

• 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
  作者：Eleuterio Alvarez、Maria T. Diaz、Ricardo Perez、Jose L. Ravelo、Alicia Regueiro、Jose A. Vera、Dacil Zurita、Julio D. Martin

  DOI：10.1021/jo00089a034

  日期：1994.5

  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.
• Alvarez, Eleuterio; Diaz, Maria Teresa; Zurita, Dacil, Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 9, p. 635 - 645
  作者：Alvarez, Eleuterio、Diaz, Maria Teresa、Zurita, Dacil、Zarraga, Miguel、Martin, Julio D.

  DOI：——

  日期：——