(1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(palmitoyloxy)propyl palmitate | 17709-53-4

• 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)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(palmitoyloxy)propyl palmitate
• 英文别名: (2'R,3'R)-chloramphenicol 1',3'-dipalmitate；Chloramphenicol dipalmitate；[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hexadecanoyloxy-3-(4-nitrophenyl)propyl] hexadecanoate
• CAS: 17709-53-4
• 化学式: C₄₃H₇₂Cl₂N₂O₇
• 分子量: 799.96
• InChiKey: IQJVTOSDGMGHCK-XQUWYEIYSA-N

物化性质

• 沸点：
  836.0±65.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  54
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

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 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)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(palmitoyloxy)propyl palmitate
  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

• Substrate imprinted lipase nanogel for one-step synthesis of chloramphenicol palmitate
  作者：Rui Wang、Yifei Zhang、Jinhai Huang、Diannan Lu、Jun Ge、Zheng Liu

  DOI：10.1039/c3gc40465j

  日期：——

  activity by 2-fold in catalyzing the transesterification reaction between para-nitrophenyl palmitate and ethanol. The effects of solvent and temperature on the yield and selectivity of the enzymatic synthesis of chloramphenicol palmitate were examined, respectively. One-step synthesis of chloramphenicol palmitate with the imprinted lipase nanogel gave a yield of ∼99% and a purity of ∼99% within 12 hours

  具有高对映体和区域选择性的酶催化对绿色化学合成法具有吸引力，但在用作反应介质的有机溶剂中活性通常较低。在这里，我们描述了一种在有机溶剂中表现出高活性的“基质印迹”脂肪酶纳米凝胶。第一步是通过水性原位聚合将脂肪酶包囊在聚丙烯酰胺纳米凝胶中。然后，在棕榈酸（一种脂肪酶的底物）存在下将脂肪酶纳米凝胶冻干，然后用石油醚萃取以从冻干的脂肪酶纳米凝胶中去除棕榈酸。压印处理了2.9倍和表观活性增加的棕榈酸的吸附能力通过在催化之间的酯交换反应的2倍对-硝基苯甲酸棕榈酸酯和乙醇。分别考察了溶剂和温度对棕榈酸氯霉素酶促合成产率和选择性的影响。用印迹脂肪酶纳米凝胶一步合成棕榈酸氯霉素，在20°C下的12小时内产率约为99％，纯度约为99％，而印迹游离脂肪酶在20小时内产率低于60％。高活性和选择性使底物印迹酶纳米凝胶成为绿色合成具有复杂结构的化学药品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.