Se-phenyl (E,E,E,E,E,E,E)-5,9,13,17,21,25,29-heptamethyl-31-[(tetrahydro-2H-pyran-2-yl)oxy]hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate | 229305-89-9

• 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: Se-phenyl (E,E,E,E,E,E,E)-5,9,13,17,21,25,29-heptamethyl-31-[(tetrahydro-2H-pyran-2-yl)oxy]hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate
• 英文别名: Se-phenyl (5E,9E,13E,17E,21E,25E,29E)-5,9,13,17,21,25,29-heptamethyl-31-(oxan-2-yloxy)hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate
• CAS: 229305-89-9
• 化学式: C₄₉H₇₄O₃Se
• 分子量: 790.085
• InChiKey: KBAMCLPKKWRAJN-VVEYLCCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.56
• 重原子数：
  53
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Se-phenyl (E,E,E,E,E,E,E)-5,9,13,17,21,25,29-heptamethyl-31-[(tetrahydro-2H-pyran-2-yl)oxy]hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以94%的产率得到Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate
  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：

  3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol 在 甲醇 、 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 sodium chlorite 、 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 2-甲基-2-丁烯 、 三丁基膦 、 4-甲基苯磺酸吡啶 、 lithium 、 二异丁基氢化铝 、 potassium carbonate 、 乙胺 、 过碘酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 、 叔丁醇 为溶剂， 反应 92.5h， 生成 Se-phenyl (E,E,E,E,E,E,E)-5,9,13,17,21,25,29-heptamethyl-31-[(tetrahydro-2H-pyran-2-yl)oxy]hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate
  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

文献信息

• Handa, Sandeep; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 843 - 845
  作者：Handa, Sandeep、Pattenden, Gerald

  DOI：——

  日期：——
• Novel Regio- and Stereoselective Cascade 6-endo-trig Cyclisations from Polyene Acyl Radical Intermediates Leading to Steroid-Like Pentacycles and Heptacycles
  作者：Sandeep Handa、Prathap S. Nair、Gerald Pattenden

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

  日期：2000.9.6

  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.