(S,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoic acid isopropyl ester | 1254361-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (S,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoic acid isopropyl ester
• 英文别名: propan-2-yl (E,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-5-hydroxy-3-oxohept-6-enoate
• CAS: 1254361-93-7
• 化学式: C₂₇H₃₀FNO₄
• 分子量: 451.538
• InChiKey: POEMLWFCUAZTLY-QZMUEMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoic acid isopropyl ester 在 sodium tetrahydroborate 、 二乙基甲氧基硼烷 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 以78%的产率得到(3R,5S,E)-7-(3-(4-氟苯基)-1-异丙基-1H-吲哚-2-基)-3,5-二羟基庚-6-烯酸异丙酯
  参考文献：
  名称：

  Facile and Highly Enantioselective Synthesis of (+)- and (−)-Fluvastatin and Their Analogues

  摘要：

  A highly enantioselective synthesis of (+)- and (-)-fluvastatin and their analogues has been facilitated by the reaction of an aldehyde with diketene in the presence of Ti(O-iota-Pr)(4) and a chiral Schiff base ligand Either enantiomer of the Schiff base could be employed to obtain (+)- or (-)-fluvastatin Diastereoselective reductions of the resultant keto moiety of beta-hydroxy ketoesters provided the syn-1,3-diol esters (91% ee), which were subsequently recrystallized and saponified to afford (+)- and (-)-fluvastatin in >99 9% ee

  DOI：

  10.1021/jo101542y
• 作为产物：
  描述：

  双乙烯酮 、 (E)-3-[3-(4-氟苯基)-1-异丙基吲哚-2-基]丙烯醛 、 异丙醇 在 titanium(IV) isopropylate 、 (S)-2-(N-3-叔丁基亚水杨基)氨基-3-甲基-1-丁醇 、 盐酸 作用下， 以 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 52.0h， 以78%的产率得到(S,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoic acid isopropyl ester
  参考文献：
  名称：

  Facile and Highly Enantioselective Synthesis of (+)- and (−)-Fluvastatin and Their Analogues

  摘要：

  A highly enantioselective synthesis of (+)- and (-)-fluvastatin and their analogues has been facilitated by the reaction of an aldehyde with diketene in the presence of Ti(O-iota-Pr)(4) and a chiral Schiff base ligand Either enantiomer of the Schiff base could be employed to obtain (+)- or (-)-fluvastatin Diastereoselective reductions of the resultant keto moiety of beta-hydroxy ketoesters provided the syn-1,3-diol esters (91% ee), which were subsequently recrystallized and saponified to afford (+)- and (-)-fluvastatin in >99 9% ee

  DOI：

  10.1021/jo101542y

文献信息

• Facile and Highly Enantioselective Synthesis of (+)- and (−)-Fluvastatin and Their Analogues
  作者：James T. Zacharia、Takanori Tanaka、Masahiko Hayashi

  DOI：10.1021/jo101542y

  日期：2010.11.19

  A highly enantioselective synthesis of (+)- and (-)-fluvastatin and their analogues has been facilitated by the reaction of an aldehyde with diketene in the presence of Ti(O-iota-Pr)(4) and a chiral Schiff base ligand Either enantiomer of the Schiff base could be employed to obtain (+)- or (-)-fluvastatin Diastereoselective reductions of the resultant keto moiety of beta-hydroxy ketoesters provided the syn-1,3-diol esters (91% ee), which were subsequently recrystallized and saponified to afford (+)- and (-)-fluvastatin in >99 9% ee