(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl decanoate | 1303598-13-1

• 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: (2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl decanoate
• 英文别名: (2'R,3'R)-chloramphenicol 3'-decanoate；[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] decanoate
• CAS: 1303598-13-1
• 化学式: C₂₁H₃₀Cl₂N₂O₆
• 分子量: 477.385
• InChiKey: DBSQTMJIFNHMON-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 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 Novozym 435 、 Candida antarctica lipase A preparation 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 72.0h， 生成 (2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(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

文献信息

• Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
  作者：Fengying Dong、Lingmeng Li、Lin Lin、Dannong He、Jingwen Chen、Wei Wei、Dongzhi Wei

  DOI：10.3390/molecules22091523

  日期：——

  reaction time, enzyme loading and water content on the synthesis of the chloramphenicol esters were studied. The synthesis of chloramphenicol propionate (0.25 M) with 4.0 g L−1 of LipBA loading gave a conversion of ~98% and a purity of ~99% within 8 h at 50 °C in 1,4-dioxane as solvent. The optimum mole ratio of vinyl propionate to chloramphenicol was increased to 5:1. This is the first report of B.

  这项工作提出了一种利用脂肪酶的高对映选择性和区域选择性来生产氯霉素酯的合成路线。使用氯霉素、不同碳链长度的酰基供体和脂肪酶LipBA（从解淀粉芽孢杆菌克隆的脂肪酶）合成了一系列氯霉素酯。在具有不同碳链长度的酰基供体中，发现丙酸乙烯酯是最好的。研究了不同有机溶剂、反应温度、反应时间、酶载量和含水量对氯霉素酯合成的影响。使用 4.0 g L-1 LipBA 负载合成氯霉素丙酸酯 (0.25 M)，在 1,4-二恶烷作为溶剂中，50 °C 下，8 小时内转化率约为 98%，纯度约为 99%。丙酸乙烯酯与氯霉素的最佳摩尔比提高到5:1。这是首次报道解淀粉芽孢杆菌脂肪酶用于氯霉素酯合成，并详细研究了使用该反应合成丙酸氯霉素。高酶活性和选择性使脂肪酶 LipBA 成为具有复杂结构的分子的绿色化学合成的有吸引力的催化剂。
• Enzymatic regioselective production of chloramphenicol esters
  作者：Ayla M.C. Bizerra、Tasso G.C. Montenegro、Telma L.G. Lemos、Maria C.F. de Oliveira、Marcos C. de Mattos、Iván Lavandera、Vicente Gotor-Fernández、Gonzalo de Gonzalo、Vicente Gotor

  DOI：10.1016/j.tet.2011.02.070

  日期：2011.4

  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.