(1R,2R)-3-(decanoyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl decanoate | 1303598-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-3-(decanoyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl decanoate
• 英文别名: (2'R,3'R)-chloramphenicol 1',3'-didecanoate；[(2R,3R)-3-decanoyloxy-2-[(2,2-dichloroacetyl)amino]-3-(4-nitrophenyl)propyl] decanoate
• CAS: 1303598-17-5
• 化学式: C₃₁H₄₈Cl₂N₂O₇
• 分子量: 631.637
• InChiKey: GIIUCTCAGKRUFB-GGXMVOPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  42
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R)-3-(decanoyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl decanoate 在 Novozym 435 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以10%的产率得到(1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl decanoate
  参考文献：
  名称：

  Enzymatic regioselective production of chloramphenicol esters

  摘要：

  An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.070
• 作为产物：
  描述：

  [(2R,3R)-3-乙酰氧基-2-[(2,2-二氯乙酰基)氨基]-3-(4-硝基苯基)丙基]乙酸酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 (1R,2R)-3-(decanoyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl decanoate
  参考文献：
  名称：

  Enzymatic regioselective production of chloramphenicol esters

  摘要：

  An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.070