(1S,2R,5Z,9S,10R,12R)-9,12-diiodo-13-oxabicyclo[8.2.1]tridec-5-en-2-ol | 124832-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,2R,5Z,9S,10R,12R)-9,12-diiodo-13-oxabicyclo[8.2.1]tridec-5-en-2-ol
• CAS: 124832-46-8；124986-38-5；132072-57-2；132072-64-1
• 化学式: C₁₂H₁₈I₂O₂
• 分子量: 448.083
• InChiKey: GGGMTNKPKDXTGX-LJHNPFQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5Z,9S,10R,12R)-9,12-diiodo-13-oxabicyclo[8.2.1]tridec-5-en-2-ol 在 camphor-10-sulfonic acid 吡啶 、 sodium periodate 、 四氧化锇 、 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 8.0h， 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：

  在 titanium(IV) isopropylate 、 碘 、 potassium carbonate 作用下， 生成 (1S,2R,5Z,9S,10R,12R)-9,12-diiodo-13-oxabicyclo[8.2.1]tridec-5-en-2-ol
  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

文献信息

• Model studies directed toward microalga polyether macrolides: A route to 12-carbon tetrahydrofuran and tetrahydropyran subunits
  作者：Miguel Zárraga、Matias L Rodríguez、Catalina Ruiz-Pérez、Julio D Martín

  DOI：10.1016/s0040-4039(01)80494-9

  日期：1989.1

  A new synthetic strategy for the regio- and stereo-specific synthesis of heterosubstituted tetrahydrofuran and tetrahydropyran systems involving intramolecular iodoetherification of 2,3-epoxy-cycloalkenols were studied. Unambiguous stereochemical assignments are available from X-ray studies.

  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。
• 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：——
• ZARRAGA, MIGUEL;RODRIGUEZ, MATIAS L.;RUIZ-PEREZ, CATALINA;MARTIN, JULIO D+, TETRAHEDRON LETT., 30,(1989) N8, C. 3725-3728
  作者：ZARRAGA, MIGUEL、RODRIGUEZ, MATIAS L.、RUIZ-PEREZ, CATALINA、MARTIN, JULIO D+

  DOI：——

  日期：——