(Z,Z)-2,6-Cyclooctadien-1-yl acetate | 23346-42-1

• 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)-2,6-Cyclooctadien-1-yl acetate
• 英文别名: 2,6-Cyclooctadien-1-yl-acetat；3-Acetoxy-cyclooctadien-(1,5)；2,6-Cyclooctadien-1-ol, acetate；[(2Z,6Z)-cycloocta-2,6-dien-1-yl] acetate
• CAS: 23346-42-1
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: VMVVNNQXNCQADS-NIOMPZRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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)-2,6-Cyclooctadien-1-yl acetate 在 bis(acetylacetonate)oxovanadium 、 tetraphenylporphyrin 咪唑 、 叔丁基过氧化氢 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 草酰氯 、 pyridine-SO3 complex 、 dimethyl sulfide borane 、 四丁基氟化铵 、 双氧水 、 碘 、 氧气 、 potassium carbonate 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 异辛烷 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 121.83h， 生成 meso-2,7-Bis<(tert-butyldimethylsiloxy)methyl>-3,6-epidioxy-4,5-didehydrooxepane
  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-cis,cis-cyclooctadiene 在 叔丁基过氧化氢 、 溶剂黄146 、 copper(l) chloride 作用下， 以 癸烷 为溶剂， 反应 52.0h， 生成 (Z,Z)-2,6-Cyclooctadien-1-yl acetate
  参考文献：
  名称：

  与环状烯丙基醇的羟基定向的一氧化二氮环加成反应。

  摘要：

  报道了一氧化氮与环状烯丙基醇之间的非对映选择性环加成反应。分离出的产物是高密度官能化的构建基块，否则，利用先前为构建无环聚酮化合物建立的现有方法和概念不容易获得这些产物。

  DOI：

  10.1021/ol7017032

文献信息

• Hydroxyl-Directed Nitrile Oxide Cycloaddition Reactions with Cyclic Allylic Alcohols
  作者：Nina Becker、Erick M. Carreira

  DOI：10.1021/ol7017032

  日期：2007.9.1

  Diastereoselective cycloaddition reactions between a nitrile oxide and cyclic allylic alcohols are reported. The products isolated are densely functionalized building blocks that are not otherwise easily accessed with existing methods and concepts previously established for the construction of acyclic polyketides.

  报道了一氧化氮与环状烯丙基醇之间的非对映选择性环加成反应。分离出的产物是高密度官能化的构建基块，否则，利用先前为构建无环聚酮化合物建立的现有方法和概念不容易获得这些产物。
• 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.