(-)-(2S,4R)-γ-hydroxynorvaline | 21704-88-1

• 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: (-)-(2S,4R)-γ-hydroxynorvaline
• 英文别名: (2S,4R)-2-Amino-4-hydroxypentanoic acid
• CAS: 21704-88-1
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: SBRVJFMQKPUAGQ-DMTCNVIQSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  343.3±32.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium hydroxide 、 2-羟基-1-萘甲醛 、 (-)-(2S,4R)-γ-hydroxynorvaline 、 manganese(II) acetate dihydrate 以 甲醇 、 乙醇 为溶剂， 以20%的产率得到
  参考文献：
  名称：

  SYNTHESIS AND CHARACTERIZATION OF MANGANESE(III) COMPLEXES OF SCHIFF BASES DERIVED FROM AMINO ACIDS AND 2-HYDROXY-1-NAPHTHALDEHYDE

  摘要：

  New complexes of Mn(III) with Schiff bases obtained by the condensation of 2-hydroxy-1-naphthaldehyde with glycine, L-alanine, L-phenylalanine, L-histidine, L-tryptophan and L-threonine have been synthesized and characterized by elemental analyses, UV, IR, magnetic susceptibility, thermogravimetry and non-aqueous titration. These complexes are coordinated through the ONO donor set derived from the carboxyl, imino and phenoxy groups of the ligands. Furthermore, the Schiff bases were obtained as solids and their structures were determined by IR, UV, H-1 NMR to compare with those of the complexes.

  DOI：

  10.1081/sim-100106856
• 作为产物：
  描述：

  (2R)-4-amino-2-methyl-2H-furan-5-one 在 Ra-Ni (W₂) sulphonic Dowex resin 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 (-)-(2S,4R)-γ-hydroxynorvaline
  参考文献：
  名称：

  Enantioselective synthesis of hydroxy α-amino acids. (-)-- and (-) --γ-hydroxynorvalines

  摘要：

  DOI：

  10.1016/s0040-4020(01)89761-1

文献信息

• Stereocontrol of palladium(ii)-catalysed aza-Claisen rearrangements using a combination of 1,3-allylic strain and a solvent mediated directing effect
  作者：Michael D. Swift、Andrew Sutherland

  DOI：10.1039/b613271e

  日期：——

  The use of a non-coordinating solvent for the aza-Claisen rearrangement of delta,epsilon-disubstituted acetimidates switches on a substrate directing effect that gives excellent stereoselectivity.

  使用非配位溶剂进行δ，ε-二取代的乙酰胺基的氮杂-克莱森重排会改变底物导向效果，从而产生出色的立体选择性。
• Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes
  作者：Carsten Schmeck、Louis S. Hegedus

  DOI：10.1021/ja00101a014

  日期：1994.11

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.
• ARIZA, JESUS;FONT, JOSEP;ORTUNO, ROSA M., TETRAHEDRON, 46,(1990) N, C. 1931-1942
  作者：ARIZA, JESUS、FONT, JOSEP、ORTUNO, ROSA M.

  DOI：——

  日期：——
• HARDING, KENN E.;MARMAN, THOMAS H.;NAM, DO-HYUN, TETRAHEDRON LETT., 29,(1988) N 14, 1627-1630
  作者：HARDING, KENN E.、MARMAN, THOMAS H.、NAM, DO-HYUN

  DOI：——

  日期：——
• SYNTHESIS AND CHARACTERIZATION OF MANGANESE(III) COMPLEXES OF SCHIFF BASES DERIVED FROM AMINO ACIDS AND 2-HYDROXY-1-NAPHTHALDEHYDE
  作者：İffet Şakiyan、Necla Gündüz、Turgut Gündüz

  DOI：10.1081/sim-100106856

  日期：2001.8.31

  New complexes of Mn(III) with Schiff bases obtained by the condensation of 2-hydroxy-1-naphthaldehyde with glycine, L-alanine, L-phenylalanine, L-histidine, L-tryptophan and L-threonine have been synthesized and characterized by elemental analyses, UV, IR, magnetic susceptibility, thermogravimetry and non-aqueous titration. These complexes are coordinated through the ONO donor set derived from the carboxyl, imino and phenoxy groups of the ligands. Furthermore, the Schiff bases were obtained as solids and their structures were determined by IR, UV, H-1 NMR to compare with those of the complexes.