(Z)-8-hydroxy-oct-2-enoic acid ethyl ester | 105214-04-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-8-hydroxy-oct-2-enoic acid ethyl ester
• 英文别名: Z-ethyl 8-hydroxy-2-octenate
• CAS: 105214-04-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: COLUEOOWVQELHN-VURMDHGXSA-N

物化性质

• 沸点：
  273.7±23.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  6-己内酯 、 ethyl diethylphosphonoacetate lithium salt 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-8-hydroxy-oct-2-enoic acid ethyl ester 、 ethyl (E)-8-hydroxyoct-2-enoate
  参考文献：
  名称：

  Diastereoselective Synthesis of Cycloalkylamines by Samarium Diiodide-Promoted Cyclizations of α-Amino Radicals Derived from α-Benzotriazolylalkenylamines

  摘要：

  The condensation of omega-unsaturated aldehydes with benzotriazole and secondary amines affords alpha-benzotriazolylalkenylamines that exist in solution as mixtures of the corresponding benzotriazol-1-yl and benzotriazol-2-yl isomers resulting from their rapid dissociation into iminium cations and the benzotriazolyl anion. The reduction of these adducts with samarium diiodide (SmI2) takes place with formation of the benzotriazolyl anion and alpha-amino alkenyl radicals that undergo 5- or 6-exo-trig cyclizations leading to substituted cycloalkyl- or cycloheteroalkylamines. The presence of an electron-withdrawing substituent in the alkene subunit is required for efficient cyclizations. The formation of cyclopentylamines takes place with unusually high 1,5-cis selectivity (hex-5-enyl radical numbering), and the presence of a 2- or 4-Me substituent also imparts high 1,2- or 1,4-trans stereoinduction, respectively. The corresponding six-membered rings, however, are formed with low diastereoselectivity. Semiempirical calculations performed on model systems suggest that a stabilizing secondary orbital interaction between the amino group and the electron-deficient alkene might in part account for the enhanced cis-selectivity encountered.

  DOI：

  10.1021/jo960957d

文献信息

• Diol desymmetrization as an approach to the synthesis of unsymmetrical dienyl diesters
  作者：David J. Phillips、Kathryn S. Pillinger、Wei Li、Angela E. Taylor、Andrew E. Graham

  DOI：10.1016/j.tet.2007.07.089

  日期：2007.10

  The tandem oxidation/Wittig olefination of unactivated diols utilizing manganese dioxide produces α,β-unsaturated hydroxy esters in high yields in a highly effective desymmetrization process. The formation of small quantities of the corresponding lactones suggests that the reaction may proceed through a lactol intermediate in some cases. The α,β-unsaturated hydroxy esters are transformed into symmetrical

  利用二氧化锰对未活化的二醇进行串联氧化/维蒂希烯化反应，可在高效的不对称化过程中以高收率产生α，β-不饱和羟基酯。少量相应内酯的形成表明，在某些情况下，反应可能会通过内酯中间体进行。使用PCC介导的第二次氧化/维蒂希烯化序列，将α，β-不饱和羟基酯转化为对称或不对称的二烯基二酯。
• An improved procedure for the two carbon homologation of esters to α, β-unsaturated esters
  作者：James M. Takacs、Mark A. Helle、Franklin L. Seely

  DOI：10.1016/s0040-4039(00)84232-x

  日期：1986.1