(+/-)-ethyl 5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5β-<4-methyl-4-<(trimethylsilyl)oxy>-1(E)-octenyl>-4α-<(triethylsilyl)oxy>-1-cyclopenten-1-yl>-2-fluoro-2(E)-pentenoate | 109976-40-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-ethyl 5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5β-<4-methyl-4-<(trimethylsilyl)oxy>-1(E)-octenyl>-4α-<(triethylsilyl)oxy>-1-cyclopenten-1-yl>-2-fluoro-2(E)-pentenoate
• 英文别名: (+/-)-ethyl 5-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-5β-{4-methyl-4-[(trimethylsilyl)oxy]-1(E)-octenyl}-4α-[(triethylsilyl)oxy]-1-cyclopenten-1-yl)-2-fluoro-2(E)-pentenoate；ethyl (E)-5-[(4S,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-[(E)-4-methyl-4-trimethylsilyloxyoct-1-enyl]-4-triethylsilyloxycyclopenten-1-yl]-2-fluoropent-2-enoate
• CAS: 109976-40-1
• 化学式: C₃₆H₆₉FO₅Si₃
• 分子量: 685.196
• InChiKey: FWKOALSLDYJOLG-NJGWCEOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.62
• 重原子数：
  45.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl 5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5β-<4-methyl-4-<(trimethylsilyl)oxy>-1(E)-octenyl>-4α-<(triethylsilyl)oxy>-1-cyclopenten-1-yl>-2-fluoro-2(E)-pentenoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (+/-)-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5β-<4-methyl-4-<(trimethylsilyl)oxy>-1(E)-octenyl>-4α-<(triethylsilyl)oxy>-1-cyclopenten-1-yl>-2-fluoro-2(E)-pentenol
  参考文献：
  名称：

  Synthesis and gastrointestinal pharmacology of the 4-fluoro analog of enisoprost

  摘要：

  A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.

  DOI：

  10.1021/jm00394a004
• 作为产物：
  描述：

  2-<1-hydroxy-3-(1,3-dioxan-2-yl)propyl>furan 在 咪唑 、 1-pentynyl copper 、 盐酸 、 六甲基磷酰三胺 、 正丁基锂 、 sodium hydride 、 zinc(II) chloride 、 三(二甲胺基)膦 作用下， 以 1,4-二氧六环 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 66.0h， 生成 (+/-)-ethyl 5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5β-<4-methyl-4-<(trimethylsilyl)oxy>-1(E)-octenyl>-4α-<(triethylsilyl)oxy>-1-cyclopenten-1-yl>-2-fluoro-2(E)-pentenoate
  参考文献：
  名称：

  Synthesis and gastrointestinal pharmacology of the 4-fluoro analog of enisoprost

  摘要：

  A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.

  DOI：

  10.1021/jm00394a004

文献信息

• COLLINS, PAUL W.;KRAMER, STEVEN W.;GULLIKSON, GARY W., J. MED. CHEM., 30,(1987) N 11, 1952-1955
  作者：COLLINS, PAUL W.、KRAMER, STEVEN W.、GULLIKSON, GARY W.

  DOI：——

  日期：——