benzyl 2-(tert-butoxycarbonylbutyrylamino)acetate | 827028-64-8

• 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: benzyl 2-(tert-butoxycarbonylbutyrylamino)acetate
• 英文别名: benzyl 2-[butanoyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate
• CAS: 827028-64-8
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: ZCOQBFIYOXOAPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-(tert-butoxycarbonylbutyrylamino)acetate 在 N,N-二甲基丙烯基脲 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以87%的产率得到benzyl 2-tert-butoxycarbonylamino-3-oxohexanoate
  参考文献：
  名称：

  Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids

  摘要：

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.024
• 作为产物：
  描述：

  叔丁氧羰基氨基-乙酸苄酯 、 丁酰氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到benzyl 2-(tert-butoxycarbonylbutyrylamino)acetate
  参考文献：
  名称：

  Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids

  摘要：

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.024

文献信息

• Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids
  作者：Kazuishi Makino、Takayuki Goto、Yasuhiro Hiroki、Yasumasa Hamada

  DOI：10.1016/j.tetasy.2008.12.024

  日期：2008.12

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.