[[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]methyl]dimethylamine | 205647-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]methyl]dimethylamine
• 英文别名: 1-[4-(4-fluorophenyl)-5-methyl-2-propan-2-yl-1H-pyrrol-3-yl]-N,N-dimethylmethanamine
• CAS: 205647-18-3
• 化学式: C₁₇H₂₃FN₂
• 分子量: 274.381
• InChiKey: QWKTVNDNVNWKBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]methyl]dimethylamine 在 sodium hydroxide 、 二乙基甲氧基硼烷 、 氢氟酸 、 potassium tert-butylate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 15.08h， 生成 (3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salt
  参考文献：
  名称：

  Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor

  摘要：

  Useful chiral synthons, (3R)- and (3S)-[(tert-butyldimethylsilyl)oxy]penta acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from(S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and(S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.

  DOI：

  10.1021/jo9722156
• 作为产物：
  描述：

  n,n-二甲基亚甲基碘化胺 、 3-(4-fluorophenyl)-2-methyl-5-propan-2-yl-1H-pyrrole 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]methyl]dimethylamine
  参考文献：
  名称：

  Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor

  摘要：

  Useful chiral synthons, (3R)- and (3S)-[(tert-butyldimethylsilyl)oxy]penta acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from(S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and(S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.

  DOI：

  10.1021/jo9722156

文献信息

• Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor
  作者：Toshiro Konoike、Tetsuo Okada、Yoshitaka Araki

  DOI：10.1021/jo9722156

  日期：1998.5.1

  Useful chiral synthons, (3R)- and (3S)-[(tert-butyldimethylsilyl)oxy]penta acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from(S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and(S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.