(S)-isopropyl 2-bromopropanoate | 114443-26-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-isopropyl 2-bromopropanoate
• 英文别名: propan-2-yl (2S)-2-bromopropanoate
• CAS: 114443-26-4
• 化学式: C₆H₁₁BrO₂
• 分子量: 195.056
• InChiKey: ODCLWDCSAGRHKS-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-isopropyl 2-bromopropanoate 、 4,10-二氮杂-12-冠4-醚 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 生成 (2R,2'S)-di-tert-butyl 2,2'-(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)dipropanoate 、 (+/-)-(2R,2'R)-di-tert-butyl 2,2'-(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)dipropanoate 、 (2R,2'R)-di-tert-butyl 2,2'-(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)dipropanoate
  参考文献：
  名称：

  A New Class of Ligands for Aqueous, Lanthanide-Catalyzed, Enantioselective Mukaiyama Aldol Reactions

  摘要：

  The development of aqueous methods for generating enantiopure beta-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral beta-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded beta-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.

  DOI：

  10.1021/ja107197p
• 作为产物：
  描述：

  (S)-2-bromopropionyl chloride 、 异丙醇 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以99%的产率得到(S)-isopropyl 2-bromopropanoate
  参考文献：
  名称：

  A New Class of Ligands for Aqueous, Lanthanide-Catalyzed, Enantioselective Mukaiyama Aldol Reactions

  摘要：

  The development of aqueous methods for generating enantiopure beta-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral beta-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded beta-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.

  DOI：

  10.1021/ja107197p

文献信息

• A New Class of Ligands for Aqueous, Lanthanide-Catalyzed, Enantioselective Mukaiyama Aldol Reactions
  作者：Yujiang Mei、Prabani Dissanayake、Matthew J. Allen

  DOI：10.1021/ja107197p

  日期：2010.9.22

  The development of aqueous methods for generating enantiopure beta-hydroxy carbonyl compounds is an important goal because these subunits compose many bioactive compounds and the ability to synthesize these groups in water has environmental and cost benefits. In this communication, we report a new class of ligands for aqueous, lanthanide-catalyzed, asymmetric Mukaiyama aldol reactions for the synthesis of chiral beta-hydroxy ketones. Furthermore, we have used luminescence-decay measurements to unveil mechanistic information regarding the catalytic reaction via changes in water-coordination number. The precatalysts presented here yielded beta-hydroxy carbonyls from aliphatic and aryl substrates with outstanding syn:anti ratios and enantiometric excesses of up to 49:1 and 97%, respectively.