(3R,5R,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoic acid isopropyl ester | 1254362-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (3R,5R,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoic acid isopropyl ester
• 英文别名: propan-2-yl (E,3R,5R)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate
• CAS: 1254362-03-2
• 化学式: C₂₇H₃₂FNO₄
• 分子量: 453.554
• InChiKey: QXMWVLOVEHOMGZ-KMWGMXNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5R,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoic acid isopropyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 氟伐他汀抗异构体
  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：

  (R,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-5-hydroxy-3-oxohept-6-enoic acid isopropyl ester 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以44%的产率得到(3R,5R,E)-7-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl)-3,5-dihydroxyhept-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