(E)-2-undec-3-en-5-ynyl-1,3-dioxolane | 624735-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (E)-2-undec-3-en-5-ynyl-1,3-dioxolane
• CAS: 624735-66-6
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: SIZMGKSVDVANPW-CMDGGOBGSA-N

物化性质

• 沸点：
  316.5±17.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-undec-3-en-5-ynyl-1,3-dioxolane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (E)-dodec-4-en-6-ynal
  参考文献：
  名称：

  Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs

  摘要：

  To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-C-14]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,12Z)-1-bromoheptadeca-5.9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO2 furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydropyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-C-14]-analogs were obtained from the bromides by carbonation with (CO2)-C-14. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00049-5
• 作为产物：
  描述：

  1-庚炔 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 6.0h， 生成 (E)-2-undec-3-en-5-ynyl-1,3-dioxolane
  参考文献：
  名称：

  Stereoselective synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-14C]-radiolabeled analogs

  摘要：

  To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne, (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid, (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid, and their [1-C-14]-analogs. In the case of (6Z,10E,12Z)-octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1-heptyne and (E)-1,2-dichloro-ethene, a coupling reaction with a Grignard reagent and cleavage of the dioxolane gave (E)-dodec-4-en-6-ynal 3. Stereoselective Wittig reaction between aldehyde 3 and triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium provided a dienyne. Stereocontrolled reduction of the triple bond and replacement of the tetrahydropyranyl group by a bromine gave (5Z,9E,12Z)-1-bromoheptadeca-5.9,11-triene 10. Formation of the alkenyl lithium derivative and carbonation with CO2 furnished (6Z,10E,12Z)-octadecatrienoic acid. (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid was obtained by the same route but using triphenyl-[5-(tetrahydropyran-2-yloxy)-heptyl]-phosphonium iodide for the Wittig reaction. [1-C-14]-analogs were obtained from the bromides by carbonation with (CO2)-C-14. In all cases, chemical or radiochemical purities were found to be better than 95% after purification by flash chromatography on silica gel (>99% after additional purification by RP-HPLC). Metabolism studies in animals are in progress. (C) 2003 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00049-5