2,11-Diiodo-9-acetoxy-13-oxabicyclo<8.2.1>tridec-5-ene | 124832-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 2,11-Diiodo-9-acetoxy-13-oxabicyclo<8.2.1>tridec-5-ene
• 英文别名: [(1S,2R,5Z,9S,10R,12R)-9,12-diiodo-13-oxabicyclo[8.2.1]tridec-5-en-2-yl] acetate
• CAS: 124832-52-6；132072-58-3
• 化学式: C₁₄H₂₀I₂O₃
• 分子量: 490.12
• InChiKey: WLZGITWILGUDBZ-UBTCCDKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,11-Diiodo-9-acetoxy-13-oxabicyclo<8.2.1>tridec-5-ene 在 吡啶 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 生成 Acetic acid (Z)-(1S,8S,9R,10R,12R)-8,12-diacetoxy-13-oxa-bicyclo[7.3.1]tridec-4-en-10-yl ester
  参考文献：
  名称：

  海洋转熔聚醚毒素四氢吡喃亚基的合成方法

  摘要：

  2,3-环氧环烷基-5-烯-1-醇的环化/溶剂化反应具有完全的区域选择性和立体选择性，生成顺式2,6-二烷基-3,5-氧化的四氢吡喃，因此分两步组装关键结构存在于海洋顺反融合聚醚毒素中的单元。

  DOI：

  10.1016/0040-4039(90)80036-l
• 作为产物：
  描述：

  在 titanium(IV) isopropylate 碘 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以66%的产率得到2,11-Diiodo-9-acetoxy-13-oxabicyclo<8.2.1>tridec-5-ene
  参考文献：
  名称：

  海洋转熔聚醚毒素四氢吡喃亚基的合成方法

  摘要：

  2,3-环氧环烷基-5-烯-1-醇的环化/溶剂化反应具有完全的区域选择性和立体选择性，生成顺式2,6-二烷基-3,5-氧化的四氢吡喃，因此分两步组装关键结构存在于海洋顺反融合聚醚毒素中的单元。

  DOI：

  10.1016/0040-4039(90)80036-l

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。
• 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：——
• 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：——