(R)-isopropyl 7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-pheny1-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxoheptanoate | 1426655-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (R)-isopropyl 7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-pheny1-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxoheptanoate
• 英文别名: (R)-isopropyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-5-hydroxy-3-oxoheptanoate；propan-2-yl (5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-5-hydroxy-3-oxoheptanoate
• CAS: 1426655-65-3
• 化学式: C₃₆H₃₉FN₂O₅
• 分子量: 598.714
• InChiKey: ZWBPZSUCUWWFHW-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-isopropyl 7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-pheny1-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxoheptanoate 在 二乙基甲氧基硼烷 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以83%的产率得到阿托伐他汀酸异丙酯
  参考文献：
  名称：

  用于钛介导的α，β-不饱和醛与双烯酮的不对称羟醛羟醛反应的新型氯霉素席夫碱配体：阿托伐他汀钙的短合成†

  摘要：

  从可商购的氯霉素碱制备了几种新颖的手性席夫碱配体，并将其应用于双烯酮与各种α，β-不饱和醛的钛介导的不对称醛醇缩合反应。该反应以高收率和高对映选择性进行。这种方法的合成效用在阿托伐他汀钙的短时合成中得到了证明。

  DOI：

  10.1039/c6ra15304f
• 作为产物：
  描述：

  1-(3,3-diethoxypropyl)-5-(4-fluoropheny)-2-(1-methylethy)-N,4-diphenyl-1H-pyrrole-3-carboxamide 在 盐酸 、 (S)-2-(N-3-叔丁基亚水杨基)氨基-3-甲基-1-丁醇 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 (R)-isopropyl 7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-pheny1-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxoheptanoate
  参考文献：
  名称：

  Synthetic studies on statins. Part 1: a short and cyanide-free synthesis of atorvastatin calcium via an enantioselective aldol strategy

  摘要：

  A short and cyanide-free enantioselective synthesis of atorvastatin calcium has been achieved starting from a commercially available highly substituted 1,4-diketone in an overall yield of 40%. The key step in this approach is the asymmetric aldol reaction of an aldehyde with diketene in the presence of Ti(O-i-Pr)(4)-Schiff base complex to create the (5R)-stereochemistry of atorvastatin calcium. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.009

文献信息

• Synthetic studies on statins. Part 1: a short and cyanide-free synthesis of atorvastatin calcium via an enantioselective aldol strategy
  作者：Lemeng Hu、Fangjun Xiong、Xiaofei Chen、Wenxue Chen、Qiuqin He、Fener Chen

  DOI：10.1016/j.tetasy.2012.12.009

  日期：2013.2

  A short and cyanide-free enantioselective synthesis of atorvastatin calcium has been achieved starting from a commercially available highly substituted 1,4-diketone in an overall yield of 40%. The key step in this approach is the asymmetric aldol reaction of an aldehyde with diketene in the presence of Ti(O-i-Pr)(4)-Schiff base complex to create the (5R)-stereochemistry of atorvastatin calcium. (C) 2013 Elsevier Ltd. All rights reserved.
• New chloramphenicol Schiff base ligands for the titanium-mediated asymmetric aldol reaction of α,β-unsaturated aldehydes with diketene: a short synthesis of atorvastatin calcium
  作者：Haifeng Wang、Linjie Yan、Fangjun Xiong、Yan Wu、Fener Chen

  DOI：10.1039/c6ra15304f

  日期：——

  Several novel chiral Schiff base ligands were prepared from a commercially available chloramphenicol base and applied to the titanium-mediated asymmetric aldol reaction of diketene with various α,β-unsaturated aldehydes. This reaction proceeded in good yield with high enantioselectivity. The synthetic utility of this methodology was demonstrated in the short synthesis of atorvastatin calcium.

  从可商购的氯霉素碱制备了几种新颖的手性席夫碱配体，并将其应用于双烯酮与各种α，β-不饱和醛的钛介导的不对称醛醇缩合反应。该反应以高收率和高对映选择性进行。这种方法的合成效用在阿托伐他汀钙的短时合成中得到了证明。