(2S,3R)-O-(n-octanoyl)-L-threonine | 1256239-23-2

• 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,3R)-O-(n-octanoyl)-L-threonine
• 英文别名: (2S,3R)-2-amino-3-octanoyloxybutanoic acid
• CAS: 1256239-23-2
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: PKPGKPNJYQGBST-KOLCDFICSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  377.7±37.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-苏氨酸 、 辛酰氯 在 三氟乙酸 、 三乙胺 作用下， 以 水 为溶剂， 反应 12.5h， 以95%的产率得到(2S,3R)-O-(n-octanoyl)-L-threonine
  参考文献：
  名称：

  Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone

  摘要：

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.022
• 作为试剂：
  描述：

  间硝基苯甲醛 、 甲氧苯胺 、 羟基丙酮 在 (2S,3R)-O-(n-octanoyl)-L-threonine 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 生成 (3R,4R)-3-hydroxy-4-(4-methoxyanilino)-4-(3-nitrophenyl)butan-2-one 、 3-hydroxy-4-(4-methoxyanilino)-4-(3-nitrophenyl)butan-2-one
  参考文献：
  名称：

  Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone

  摘要：

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.022

文献信息

• Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone
  作者：Chuanlong Wu、Xiangkai Fu、Shi Li

  DOI：10.1016/j.tetasy.2011.06.022

  日期：2011.5

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.