(6E,10Z,14E)-16-(tert-Butyl-diphenyl-silanyloxy)-10-cyano-2,6,14-trimethyl-3-oxo-hexadeca-6,10,14-trienoic acid ethyl ester | 202338-77-0

• 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: (6E,10Z,14E)-16-(tert-Butyl-diphenyl-silanyloxy)-10-cyano-2,6,14-trimethyl-3-oxo-hexadeca-6,10,14-trienoic acid ethyl ester
• 英文别名: ethyl (6E,10Z,14E)-16-[tert-butyl(diphenyl)silyl]oxy-10-cyano-2,6,14-trimethyl-3-oxohexadeca-6,10,14-trienoate
• CAS: 202338-77-0
• 化学式: C₃₈H₅₁NO₄Si
• 分子量: 613.913
• InChiKey: DEOHNULUMKQEKQ-KTHCJELGSA-N

物化性质

• 沸点：
  675.9±55.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6E,10Z,14E)-16-(tert-Butyl-diphenyl-silanyloxy)-10-cyano-2,6,14-trimethyl-3-oxo-hexadeca-6,10,14-trienoic acid ethyl ester 在 copper diacetate 、 四丁基氟化铵 、 manganese triacetate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 生成 d,l-(1α,4aα,4bβ,7β,8β,10aβ)-ethyl 8a-cyano-7,7-(epoxymethylene)-8-(hydroxymethyl)-1,4a-dimethyl-2-oxo-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-1-phentharenecarboxylate
  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 (6E,10Z,14E)-16-(tert-Butyl-diphenyl-silanyloxy)-10-cyano-2,6,14-trimethyl-3-oxo-hexadeca-6,10,14-trienoic acid ethyl ester
  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.