trans-4-(methoxycarbonyl)-5-(heptafluoropropyl)-5-methyl-2-oxazoline

• 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: trans-4-(methoxycarbonyl)-5-(heptafluoropropyl)-5-methyl-2-oxazoline
• 英文别名: methyl (4R,5R)-5-(1,1,2,2,3,3,3-heptafluoropropyl)-5-methyl-4H-1,3-oxazole-4-carboxylate
• 化学式: C₉H₈F₇NO₃
• 分子量: 311.156
• InChiKey: IZLNXFIWTRHBTR-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,3,4,4,5,5,5-七氟戊-2-酮 、 异腈基乙酸甲酯 在 三乙胺 、 copper(l) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以88%的产率得到trans-4-(methoxycarbonyl)-5-(heptafluoropropyl)-5-methyl-2-oxazoline
  参考文献：
  名称：

  Transition Metal/Base-Catalyzed Aldol Reactions of Isocyanoacetic Acid Derivatives with Prochiral Ketones, a Straightforward Approach to Stereochemically Defined β,β-Disubstituted-β-hydroxy-α-amino Acids.¹ Scope and Limitations

  摘要：

  A systematic study of the transition metal/base-catalyzed aldol reactions of methyl isocyanoacetate with a wide range of prochiral ketones, giving rise to the 4-(methoxycarbonyl)-5,5-disubstituted-2-oxazolines, has been made. The diastereoselectivity of these reactions was found to be influenced by a mix of several factors, including steric characteristic of the substituents, nature of the catalyst, electrostatic, and electron donor-acceptor type interactions. The former factor, a stereochemical discrimination between the substituents at the ketone carbon, was shown to be the most pronounced in controlling of the stereochemical outcome, which could be markedly improved with a proper choice of the catalyst. In particular, for the reactions of methyl isocyanoacetate with polyhaloalkyl aryl(alkyl) ketones, high diastereoselectivity (80-98% de) was achieved, thus allowing for straightforward and generalized access to the corresponding (2R*,3R*)-beta,beta-disubstituted-beta-hydroxy-alpha-amino carboxylic acid.

  DOI：

  10.1021/jo9623402

文献信息

• Transition Metal/Base-Catalyzed Aldol Reactions of Isocyanoacetic Acid Derivatives with Prochiral Ketones, a Straightforward Approach to Stereochemically Defined β,β-Disubstituted-β-hydroxy-α-amino Acids.¹ Scope and Limitations
  作者：Vadim A. Soloshonok、Alexey D. Kacharov、Dimitry V. Avilov、Kohki Ishikawa、Nobuya Nagashima、Tamio Hayashi

  DOI：10.1021/jo9623402

  日期：1997.5.1

  A systematic study of the transition metal/base-catalyzed aldol reactions of methyl isocyanoacetate with a wide range of prochiral ketones, giving rise to the 4-(methoxycarbonyl)-5,5-disubstituted-2-oxazolines, has been made. The diastereoselectivity of these reactions was found to be influenced by a mix of several factors, including steric characteristic of the substituents, nature of the catalyst, electrostatic, and electron donor-acceptor type interactions. The former factor, a stereochemical discrimination between the substituents at the ketone carbon, was shown to be the most pronounced in controlling of the stereochemical outcome, which could be markedly improved with a proper choice of the catalyst. In particular, for the reactions of methyl isocyanoacetate with polyhaloalkyl aryl(alkyl) ketones, high diastereoselectivity (80-98% de) was achieved, thus allowing for straightforward and generalized access to the corresponding (2R*,3R*)-beta,beta-disubstituted-beta-hydroxy-alpha-amino carboxylic acid.