(E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trienenitrile | 314739-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trienenitrile
• CAS: 314739-76-9
• 化学式: C₂₃H₃₇NO₂
• 分子量: 359.552
• InChiKey: NKPBVKOHAIEODB-FFVKMRADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  26.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trienenitrile 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以81%的产率得到(E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trienal
  参考文献：
  名称：

  Novel Regio- and Stereoselective Cascade 6-endo-trig Cyclisations from Polyene Acyl Radical Intermediates Leading to Steroid-Like Pentacycles and Heptacycles

  摘要：

  In a quite remarkable regio- and stereoselective manner, each of the (all-E)-polyene selenoates 5a-c is shown to undergo cascade radical-mediated polycyclisations via consecutive 6-endo-trig reactions, leading to the corresponding all-trans, anti, tri-, penta- and heptacycles, i.e., 20, 23, and 25, in good yields. The configurations of these 'steroid-like' polycycles followed from detailed examination and correlation of chemical shift data in their C-13-NMR spectra.

  DOI：

  10.1002/1522-2675(20000906)83:9<2629::aid-hlca2629>3.0.co;2-w
• 作为产物：
  描述：

  geranylgeranyl acetate 在 甲醇 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 过碘酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 68.0h， 生成 (E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trienenitrile
  参考文献：
  名称：

  Novel Regio- and Stereoselective Cascade 6-endo-trig Cyclisations from Polyene Acyl Radical Intermediates Leading to Steroid-Like Pentacycles and Heptacycles

  摘要：

  In a quite remarkable regio- and stereoselective manner, each of the (all-E)-polyene selenoates 5a-c is shown to undergo cascade radical-mediated polycyclisations via consecutive 6-endo-trig reactions, leading to the corresponding all-trans, anti, tri-, penta- and heptacycles, i.e., 20, 23, and 25, in good yields. The configurations of these 'steroid-like' polycycles followed from detailed examination and correlation of chemical shift data in their C-13-NMR spectra.

  DOI：

  10.1002/1522-2675(20000906)83:9<2629::aid-hlca2629>3.0.co;2-w