(2Z,6E)-8-(tert-Butyl-diphenyl-silanyloxy)-2-((E)-5-hydroxy-4-methyl-pent-3-enyl)-6-methyl-octa-2,6-dienenitrile | 202339-01-3

• 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: (2Z,6E)-8-(tert-Butyl-diphenyl-silanyloxy)-2-((E)-5-hydroxy-4-methyl-pent-3-enyl)-6-methyl-octa-2,6-dienenitrile
• 英文别名: (2Z,6E)-8-[tert-butyl(diphenyl)silyl]oxy-2-[(E)-5-hydroxy-4-methylpent-3-enyl]-6-methylocta-2,6-dienenitrile
• CAS: 202339-01-3
• 化学式: C₃₁H₄₁NO₂Si
• 分子量: 487.758
• InChiKey: RLPWHOOMPJYABR-HTXNCDABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z,6E)-8-(tert-Butyl-diphenyl-silanyloxy)-2-((E)-5-hydroxy-4-methyl-pent-3-enyl)-6-methyl-octa-2,6-dienenitrile 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 copper diacetate 、 四丁基氟化铵 、 sodium acetate 、 manganese triacetate 、 dipyridine chromium trioxide 、 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 42.25h， 生成 (3bS,5aR,6S,9aS,9bR)-6-Hydroxymethyl-6,9a-dimethyl-5,5a,6,9,9a,9b,10,11-octahydro-4H-phenanthro[1,2-c]furan-3b-carbaldehyde
  参考文献：
  名称：

  Advanced Tetracycles in a Stereoselective Approach to d,l-Spongiatriol and Related Metabolites:  The Use of Radicals in the Synthesis of Angular Electrophores

  摘要：

  A stereoselective radical cascade cyclization of polyene 6, containing an alpha,beta-unsaturated cyano group, was employed to control six contiguous chiral centers and to introduce a C-8 angular CN group in tricycle 7, The cyano group was ultimately utilized as an entry to a C-8 angular hydroxymethyl group, Compound 7 was converted inter two key tetracycles 22 and 25, respectively, each possessing an intact D-furan ring system and containing the necessary functionality for further chemical elaboration to the highly oxygenated spongians 1-5.

  DOI：

  10.1021/jo971632f
• 作为产物：
  描述：

  (E)-6-((tert-butyldiphenylsilyl)oxy-4methylhex-4-enal) 在 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 生成 (2Z,6E)-8-(tert-Butyl-diphenyl-silanyloxy)-2-((E)-5-hydroxy-4-methyl-pent-3-enyl)-6-methyl-octa-2,6-dienenitrile
  参考文献：
  名称：

  Advanced Tetracycles in a Stereoselective Approach to d,l-Spongiatriol and Related Metabolites:  The Use of Radicals in the Synthesis of Angular Electrophores

  摘要：

  A stereoselective radical cascade cyclization of polyene 6, containing an alpha,beta-unsaturated cyano group, was employed to control six contiguous chiral centers and to introduce a C-8 angular CN group in tricycle 7, The cyano group was ultimately utilized as an entry to a C-8 angular hydroxymethyl group, Compound 7 was converted inter two key tetracycles 22 and 25, respectively, each possessing an intact D-furan ring system and containing the necessary functionality for further chemical elaboration to the highly oxygenated spongians 1-5.

  DOI：

  10.1021/jo971632f

文献信息

• Advanced Tetracycles in a Stereoselective Approach to <i>d,l</i>-Spongiatriol and Related Metabolites:  The Use of Radicals in the Synthesis of Angular Electrophores
  作者：Phillip A. Zoretic、Yongzheng Zhang、Haiquan Fang、Anthony A. Ribeiro、George Dubay

  DOI：10.1021/jo971632f

  日期：1998.2.1

  A stereoselective radical cascade cyclization of polyene 6, containing an alpha,beta-unsaturated cyano group, was employed to control six contiguous chiral centers and to introduce a C-8 angular CN group in tricycle 7, The cyano group was ultimately utilized as an entry to a C-8 angular hydroxymethyl group, Compound 7 was converted inter two key tetracycles 22 and 25, respectively, each possessing an intact D-furan ring system and containing the necessary functionality for further chemical elaboration to the highly oxygenated spongians 1-5.