(4-chlorophenyl) (2R)-2-[4-(2-methylpropyl)phenyl]propanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4-chlorophenyl) (2R)-2-[4-(2-methylpropyl)phenyl]propanoate
• 化学式: C₁₉H₂₁ClO₂
• 分子量: 316.828
• InChiKey: DOYBYBQAJTUZDN-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-4-异丁基苯 、 4-chlorophenyl 2-bromopropanoate 在 magnesium 、 (4S,4'S)-2,2'-((1S,2R)-3,3-dimethylcyclopropane-1,2-diyl)bis(4-isobutyl-4,5-dihydrooxazole) 、 cobalt(II) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 11.3h， 以74%的产率得到
  参考文献：
  名称：

  Asymmetric cross-coupling of racemic α-bromo esters with aryl Grignard reagents catalyzed by cyclopropane-based bisoxazolines cobalt complexes

  摘要：

  Four new cyclopropane-based bisoxazolines were synthesized and applied to cobalt-catalyzed cross-coupling reactions between racemic alpha-bromo esters and aryl Grignard reagents. The reaction afforded a series of chiral alpha-arylalkanoic esters with high yields and good enantioselectivities (up to 93% yield, 92:8 er). This research focuses on the cross-coupling between racemic alpha-bromopropanoate and p-isobutylphenyl Grignard reagent's which provides ibuprofen ester efficiently. Furthermore, ibuprofen ester 7e was transformed into (S) -ibuprofen (99:1 er) via hydrolysis and recrystallization. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.05.010

文献信息

• Asymmetric cross-coupling of racemic α-bromo esters with aryl Grignard reagents catalyzed by cyclopropane-based bisoxazolines cobalt complexes
  作者：Feipeng Liu、Qinghua Bian、Jianyou Mao、Zidong Gao、Dan Liu、Shikuo Liu、Xueyang Wang、Yu Wang、Min Wang、Jiangchun Zhong

  DOI：10.1016/j.tetasy.2016.05.010

  日期：2016.8

  Four new cyclopropane-based bisoxazolines were synthesized and applied to cobalt-catalyzed cross-coupling reactions between racemic alpha-bromo esters and aryl Grignard reagents. The reaction afforded a series of chiral alpha-arylalkanoic esters with high yields and good enantioselectivities (up to 93% yield, 92:8 er). This research focuses on the cross-coupling between racemic alpha-bromopropanoate and p-isobutylphenyl Grignard reagent's which provides ibuprofen ester efficiently. Furthermore, ibuprofen ester 7e was transformed into (S) -ibuprofen (99:1 er) via hydrolysis and recrystallization. (C) 2016 Elsevier Ltd. All rights reserved.