(Z,Z)-1-acetoxy-cyclodeca-2,7-diene | 118620-19-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z,Z)-1-acetoxy-cyclodeca-2,7-diene
• 英文别名: (Z,Z)-1-Acetoxy-2,7-cyclodecadiene；[(2Z,7Z)-cyclodeca-2,7-dien-1-yl] acetate
• CAS: 118620-19-2
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: WFMWRVQALSTVIV-PGNVZPTMSA-N

物化性质

• 沸点：
  261.8±40.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z,Z)-1-acetoxy-cyclodeca-2,7-diene 在 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 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
• 作为产物：
  描述：

  1,5-二烯环十烷 在 copper(I) chloride 、 aluminum oxide 、 sodium 叔丁基过氧化氢 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 (Z,Z)-1-acetoxy-cyclodeca-2,7-diene
  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

文献信息

• Model studies directed towards microalga polyether toxins. A stereoselective entry into C10 cis and trans fused oxane-oxepane subunits
  作者：Eleuterio Alvarez、Dácil Zurita、Julio D. Martín

  DOI：10.1016/s0040-4039(00)79692-4

  日期：1991.5

  A new synthetic process for the construction of cis- and trans-fused oxane-oxepane systems starting from (Z,Z)-cyclodeca-2,7-dien-1-ol is described. The Ti(OiPr)4-catalysed transannular oxirane rig expansion is invoked to explain the chemoselective formation of the 11-oxobicyclo[4.4.1] undecane intermediate.

  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。
• Tricyclic oxonium-directed addition: Regiochemistry and stereochemistry of the electrophilic additions to epoxy cycloalkenols.
  作者：Eleuterio Alvarez、Eduardo Manta、Julio D Martin、Matias L Rodriguez、Catalina Ruiz-Perez、Dacil Zurita

  DOI：10.1016/s0040-4039(00)87844-2

  日期：——

  The regio- and stereochemistry of electrophile-promoted transannular ring expansion of cyclo 1,5- and 1,6-epoxyalkenes and cyclo trans-1,5-bisepoxides were studied. The results are rationalized in terms of tricyclic oxonium intermediates showing the directing ability of oxygen substituents in the regio- and stereocontrol observed.

  研究了亲电子试剂促进的环1,5-和1,6-环氧烯烃和环反1,5-双环氧化物的亲电促进的跨环扩环的区域和立体化学。就三环氧鎓中间体而言，该结果是合理的，该中间体显示了在所观察到的区域和立体控制中氧取代基的定向能力。
• ALVAREZ, ELEUTERIO;MANTA, EDUARDO;MARTIN, JULIO D.;RODRIQUEZ, MATIAS L.;R+, TETRAHEDRON LETT., 29,(1988) N 17, 2097-2100
  作者：ALVAREZ, ELEUTERIO、MANTA, EDUARDO、MARTIN, JULIO D.、RODRIQUEZ, MATIAS L.、R+

  DOI：——

  日期：——