trans-5,6-epoxy-cis-cyclodecene | 24639-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: trans-5,6-epoxy-cis-cyclodecene
• 英文别名: trans-1,2-Epoxy-cis-cyclododecen-(5)
• CAS: 24639-32-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ZNDXMXPLDKMKRO-CVLTWBRKSA-N

物化性质

• 沸点：
  38 °C(Press: 0.1 Torr)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.53
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trans-5,6-epoxy-cis-cyclodecene 生成 环癸醇
  参考文献：
  名称：

  Schank,K.; Eistert,B., Chemische Berichte, 1966, vol. 99, p. 1414 - 1430

  摘要：

  DOI：
• 作为产物：
  描述：

  1,5-二烯环十烷 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以93%的产率得到trans-5,6-epoxy-cis-cyclodecene
  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

• Friedel-Crafts cyclialkylations of some epoxides. 2. Stereospecificity, substituent, product, and kinetic studies
  作者：Stephen K. Taylor、Mark E. Davisson、B. Rolf Hissom、Sandra L. Brown、Holle A. Pristach、Scott B. Schramm、Suzanne M. Harvey

  DOI：10.1021/jo00379a021

  日期：1987.2
• Highly stereoselective Friedel-Crafts alkylations via epoxide transannular reactions
  作者：Stephen K. Taylor、Gay L. Lilley、Kevin J. Lilley、Patricia A. McCoy

  DOI：10.1021/jo00326a021

  日期：1981.6
• Schank,K.; Eistert,B., Chemische Berichte, 1966, vol. 99, p. 1414 - 1430
  作者：Schank,K.、Eistert,B.

  DOI：——

  日期：——
• 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.