[(4S)-3-methyl-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]acetic acid | 261943-09-3

• 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: [(4S)-3-methyl-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]acetic acid
• 英文别名: 2-[(4S)-3-methyl-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]acetic acid
• CAS: 261943-09-3
• 化学式: C₈H₇F₆NO₄
• 分子量: 295.138
• InChiKey: VEXIXQDCQSTLRT-VKHMYHEASA-N

物化性质

• 沸点：
  336.9±42.0 °C(Predicted)
• 密度：
  1.603±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(4S)-3-methyl-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]acetic acid 在 sulfur tetrafluoride 作用下， 反应 24.0h， 以44%的产率得到(4S)-3-methyl-4-(2,2,2-trifluoroethyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one
  参考文献：
  名称：

  New Stereoconservative Syntheses of β,β,β- and γ,γ,γ-Trifluoro-α-amino, α-Hydroxy, and α-Mercapto Acids and Their Incorporation into a Peptide and Depsipeptide Fragment

  摘要：

  描述了使用六氟丙酮作为保护和活化试剂合成β、β、β-和γ、γ、γ-三氟-α-氨基、α-羟基和α-巯基酸。合成的关键步骤是用四氟化硫处理将β-羧基转化为三氟甲基。获得的羧基活化物质适合直接掺入肽和缩酚肽片段中。 RP-HPLC 实验和 Mosher 的 TMPA 方法（1H 和 19F）证明反应序列的发生没有外消旋作用。

  DOI：

  10.1055/s-2000-8198
• 作为产物：
  描述：

  [(4S)-3-methyl-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]acetyl chloride 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以74%的产率得到[(4S)-3-methyl-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]acetic acid
  参考文献：
  名称：

  A New Approach toN-Methylaspartic,N-Methylglutamic, andN-Methyl-α-aminoadipic Acid Derivatives

  摘要：

  N-Methylaspartic acid derivatives and its homologues are obtained by a stereoconservative one-pot procedure from hexafluoroacetone-protected aspartic and glutamic acid, 2a and 2b, respectively. alpha-Aminoadipic acid (5c) and its derivative 6c are accessible from the corresponding glutamic acid derivative 9b by a Wolff rearrangement. A variety of homochiral N-methylamino acids, 5 and 12, and their derivatives, 6 and 8-11, become readily available by the new synthetic concept.

  DOI：

  10.1002/(sici)1099-0690(200001)2000:1<199::aid-ejoc199>3.0.co;2-8

文献信息

• A New Approach toN-Methylaspartic,N-Methylglutamic, andN-Methyl-α-aminoadipic Acid Derivatives
  作者：Klaus Burger、Jan Spengler

  DOI：10.1002/(sici)1099-0690(200001)2000:1<199::aid-ejoc199>3.0.co;2-8

  日期：2000.1

  N-Methylaspartic acid derivatives and its homologues are obtained by a stereoconservative one-pot procedure from hexafluoroacetone-protected aspartic and glutamic acid, 2a and 2b, respectively. alpha-Aminoadipic acid (5c) and its derivative 6c are accessible from the corresponding glutamic acid derivative 9b by a Wolff rearrangement. A variety of homochiral N-methylamino acids, 5 and 12, and their derivatives, 6 and 8-11, become readily available by the new synthetic concept.
• New Stereoconservative Syntheses of β,β,β- and γ,γ,γ-Trifluoro-α-amino, α-Hydroxy, and α-Mercapto Acids and Their Incorporation into a Peptide and Depsipeptide Fragment
  作者：Hartmut Schedel、Wojciech Dmowski、Klaus Burger

  DOI：10.1055/s-2000-8198

  日期：——

  Syntheses of β,β,β- and γ,γ,γ-trifluoro-α-amino, α-hydroxy and α-mercapto acids using hexafluoroacetone as protecting and activating reagent are described. The key step of the syntheses is the transformation of an ω-carboxy group into a trifluoromethyl group on treatment with sulfur tetrafluoride. The carboxy activated species obtained are suitable for direct incorporation into peptide and depsipeptide fragments. RP-HPLC experiments and Mosher's TMPA method (1H and 19F) demonstrate that the reaction sequence occurs without racemization.

  描述了使用六氟丙酮作为保护和活化试剂合成β、β、β-和γ、γ、γ-三氟-α-氨基、α-羟基和α-巯基酸。合成的关键步骤是用四氟化硫处理将β-羧基转化为三氟甲基。获得的羧基活化物质适合直接掺入肽和缩酚肽片段中。 RP-HPLC 实验和 Mosher 的 TMPA 方法（1H 和 19F）证明反应序列的发生没有外消旋作用。