ethyl (2S)-2-(dibenzylamino)-4-methylpentanoate | 171815-90-0

• 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: ethyl (2S)-2-(dibenzylamino)-4-methylpentanoate
• CAS: 171815-90-0
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: ZKWHADVTQSRXAQ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-2-(dibenzylamino)-4-methylpentanoate 在 lithium aluminium tetrahydride 、 甲基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.5h， 生成 (2R,1'S)-2-[1-(dibenzylamino)-3-methylbutyl]oxirane
  参考文献：
  名称：

  High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from .alpha.-Amino Acids

  摘要：

  alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.

  DOI：

  10.1021/jo00126a019
• 作为产物：
  描述：

  L-亮氨酸乙酯 、 溴甲苯 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 ethyl (2S)-2-(dibenzylamino)-4-methylpentanoate
  参考文献：
  名称：

  High Diastereoselective Synthesis of Threo or Erythro Aminoalkyl Epoxides from .alpha.-Amino Acids

  摘要：

  alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.

  DOI：

  10.1021/jo00126a019

文献信息

• Synthesis of Enantiopure α‘-Amino α,β-Epoxy Ketones from α‘-Amino Bromomethyl Ketones
  作者：José Barluenga、Beatriz Baragaña、José M. Concellón、Alejandro Piñera-Nicolás、M. Rosario Díaz、Santiago García-Granda

  DOI：10.1021/jo982435z

  日期：1999.7.1

  Preparation of enantiomerically pure α'-amino α,β-epoxy ketones 2 in an efficient synthesis starting from α'-amino bromomethyl ketones 5 and the obtention of amino diepoxido 10a as synthetic application of 2 are described. We also report the generalization of the synthesis of 1-aminoalkyl halomethyl ketones to their bromo derivatives.

  描述了从 α'-氨基溴甲基酮 5 开始的有效合成中制备对映体纯 α'-氨基 α,β-环氧酮 2 和获得氨基二环氧化物 10a 作为 2 的合成应用。我们还报告了 1-氨基烷基卤代甲基酮合成到它们的溴衍生物的泛化。
• ——
  作者：I. L. Lysenko、O. G. Kulinkovich

  DOI：10.1023/a:1013158900003

  日期：——

  The reaction of N-benzyl alpha-amino acid ethyl esters with ethylmagnesium bromide in the presence of a catalytic amount of titanium tetraisopropoxide leads to formation of the corresponding 1-aminoalkyl-1-cyclopropanols in high yields. Hydrogenation of the latter over palladium catalyst ensures selective removal of one or two protecting benzyl groups from the nitrogen atom.