(E,E,E,E,E,E,E)-4,8,12,16,20,24,28-heptamethyl-30-[(tetrahydro-2H-pyran-2-yl)oxy]triaconta-4,8,12,16,20,24,28-heptaen-1-ol | 229305-85-5

• 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,E,E,E,E)-4,8,12,16,20,24,28-heptamethyl-30-[(tetrahydro-2H-pyran-2-yl)oxy]triaconta-4,8,12,16,20,24,28-heptaen-1-ol
• 英文别名: (4E,8E,12E,16E,20E,24E,28E)-4,8,12,16,20,24,28-heptamethyl-30-(oxan-2-yloxy)triaconta-4,8,12,16,20,24,28-heptaen-1-ol
• CAS: 229305-85-5
• 化学式: C₄₂H₇₀O₃
• 分子量: 623.016
• InChiKey: JCEGMXXQCZHHMZ-FXLRUNKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  45
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,E,E,E,E,E,E)-4,8,12,16,20,24,28-heptamethyl-30-[(tetrahydro-2H-pyran-2-yl)oxy]triaconta-4,8,12,16,20,24,28-heptaen-1-ol 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 (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-heptaenenitrile
  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 tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 lithium 、 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 为溶剂， 反应 66.0h， 生成 (E,E,E,E,E,E,E)-4,8,12,16,20,24,28-heptamethyl-30-[(tetrahydro-2H-pyran-2-yl)oxy]triaconta-4,8,12,16,20,24,28-heptaen-1-ol
  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.