ethyl (E)-4-hydroxyoct-2-en-7-ynoate | 517893-69-5

• 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: ethyl (E)-4-hydroxyoct-2-en-7-ynoate
• CAS: 517893-69-5
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: HZCYXFQTZHCHQL-BQYQJAHWSA-N

物化性质

• 沸点：
  292.8±40.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-hydroxyoct-2-en-7-ynoate 在 2,6-二甲基吡啶 、 dicobalt octacarbonyl 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 (3aR,4R,5R,8aR)-2-Methyl-1,3-dioxo-5-triisopropylsilanyloxy-1,2,3,3a,4,5,6,7,8,8a-decahydro-cyclopenta[f]isoindole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Intramolecular Pauson−Khand Reactions of α,β-Unsaturated Esters and Related Electron-Deficient Olefins

  摘要：

  The intramolecular Pauson-Khand (PK) reaction of a variety of electron-poor enynes having an ester, cyano, or phosphonate group at the olefin terminus is described. Depending on the reaction conditions and substitution at the enyne, their dicobalthexacarbonyl complexes led preferentially to the exocyclic 1,3-diene or to the PK cyclopentenone product. In general, the 1,3-diene was obtained as the major product under N-oxide-promoted conditions, while the PK product was selectively formed in refluxing acetonitrile.

  DOI：

  10.1021/jo026828g
• 作为产物：
  描述：

  5-己炔醛 、 ethyl p-tolylsulfinylacetate 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以83%的产率得到ethyl (E)-4-hydroxyoct-2-en-7-ynoate
  参考文献：
  名称：

  Intramolecular Pauson−Khand Reactions of α,β-Unsaturated Esters and Related Electron-Deficient Olefins

  摘要：

  The intramolecular Pauson-Khand (PK) reaction of a variety of electron-poor enynes having an ester, cyano, or phosphonate group at the olefin terminus is described. Depending on the reaction conditions and substitution at the enyne, their dicobalthexacarbonyl complexes led preferentially to the exocyclic 1,3-diene or to the PK cyclopentenone product. In general, the 1,3-diene was obtained as the major product under N-oxide-promoted conditions, while the PK product was selectively formed in refluxing acetonitrile.

  DOI：

  10.1021/jo026828g

文献信息

• Mild and Efficient Molybdenum-Mediated Pauson−Khand-Type Reaction
  作者：Javier Adrio、Marta Rodríguez Rivero、Juan Carlos Carretero

  DOI：10.1021/ol047678u

  日期：2005.2.1

  Pauson-Khand reaction promoted by Mo(CO)3(DMF)3 takes place under very mild conditions in the absence of any promoter. High yields in Pauson-Khand adducts are obtained in the cyclization of a wide variety of functionalized 1,6- and 1,7-enynes. Enynes bearing electron withdrawing groups at the alkene terminus are particularly good substrates.

  [反应：见正文]由Mo（CO）3（DMF）3促进的钼介导的Pauson-Khand反应在非常温和的条件下发生，没有任何启动子。在多种功能化的1,6-和1,7-烯炔的环化反应中，Pauson-Khand加合物的收率很高。在烯烃末端带有吸电子基团的烯炔是特别好的底物。