(R)-(-)-2-N-formylamino-butyric acid | 783357-29-9

• 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: (R)-(-)-2-N-formylamino-butyric acid
• 英文别名: (2R)-2-formamidobutanoic acid
• CAS: 783357-29-9
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: QAISXTKWTBOYAA-SCSAIBSYSA-N

物化性质

• 熔点：
  153-155 °C(Solv: water (7732-18-5))
• 沸点：
  367.6±25.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-N-formylamino-butyric acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(R)-(-)-2-N-Methylamino-1-butanol
  参考文献：
  名称：

  Synthesis of chiral pentacyclo-undecane ligands and their use in the enantioselective alkylation of benzaldehyde with diethylzinc

  摘要：

  The synthesis of a new class of chiral pentacycloundecane cage annulated bidentate ligands is reported. This class of ligands can be used in many reactions that are catalysed by amino alcohol ligands. The ability of the chiral ligands to asymmetrically catalyse the reaction between diethylzinc and benzaldehyde was investigated. The cage annulated bidentate ligands have C, symmetry and showed poor to good enantioselectivity with high yields compared to previous systems reported using other amino alcohol ligands. An important conclusion from the results is that both ligands should be involved in the mechanism as the bidentate ligands gives much improved enantioselectivity when compared with a single chiral source molecule. This system could be utilised as a versatile probe for examining the reaction mechanism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.038
• 作为产物：
  描述：

  甲酸 、 D-2-氨基丁酸 在 乙酸酐 作用下， 以63%的产率得到(R)-(-)-2-N-formylamino-butyric acid
  参考文献：
  名称：

  Synthesis of chiral pentacyclo-undecane ligands and their use in the enantioselective alkylation of benzaldehyde with diethylzinc

  摘要：

  The synthesis of a new class of chiral pentacycloundecane cage annulated bidentate ligands is reported. This class of ligands can be used in many reactions that are catalysed by amino alcohol ligands. The ability of the chiral ligands to asymmetrically catalyse the reaction between diethylzinc and benzaldehyde was investigated. The cage annulated bidentate ligands have C, symmetry and showed poor to good enantioselectivity with high yields compared to previous systems reported using other amino alcohol ligands. An important conclusion from the results is that both ligands should be involved in the mechanism as the bidentate ligands gives much improved enantioselectivity when compared with a single chiral source molecule. This system could be utilised as a versatile probe for examining the reaction mechanism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.038

文献信息

• Synthesis of chiral pentacyclo-undecane ligands and their use in the enantioselective alkylation of benzaldehyde with diethylzinc
  作者：Grant A. Boyle、Thavendran Govender、Hendrik G. Kruger、Glenn E.M. Maguire

  DOI：10.1016/j.tetasy.2004.07.038

  日期：2004.9

  The synthesis of a new class of chiral pentacycloundecane cage annulated bidentate ligands is reported. This class of ligands can be used in many reactions that are catalysed by amino alcohol ligands. The ability of the chiral ligands to asymmetrically catalyse the reaction between diethylzinc and benzaldehyde was investigated. The cage annulated bidentate ligands have C, symmetry and showed poor to good enantioselectivity with high yields compared to previous systems reported using other amino alcohol ligands. An important conclusion from the results is that both ligands should be involved in the mechanism as the bidentate ligands gives much improved enantioselectivity when compared with a single chiral source molecule. This system could be utilised as a versatile probe for examining the reaction mechanism. (C) 2004 Elsevier Ltd. All rights reserved.