[R-(R*,R*)]-2-(2,2-二氯乙酰氨基)-3-羟基-3-(4-硝基苯基)乙基苯甲酸酯 | 492-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [R-(R*,R*)]-2-(2,2-二氯乙酰氨基)-3-羟基-3-(4-硝基苯基)乙基苯甲酸酯
• 英文名称: (2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl benzoate
• 英文别名: (2'R,3'R)-chloramphenicol 3'-benzoate；(1R,2R)-3-benzoyloxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol；(1R,2R)-3-Benzoyloxy-2-(2,2-dichlor-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol；[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] benzoate
• CAS: 492-79-5
• 化学式: C₁₈H₁₆Cl₂N₂O₆
• 分子量: 427.241
• InChiKey: DZMRHMRHPZEMEV-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [R-(R*,R*)]-2-(2,2-二氯乙酰氨基)-3-羟基-3-(4-硝基苯基)乙基苯甲酸酯 在 吡啶 、 氯化亚砜 作用下， 生成 (1S,2R)-3-benzoyloxy-1-chloro-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propane
  参考文献：
  名称：

  Diastereoisomeric propane derivatives and process for their manufacture

  摘要：

  公开号：

  US02663727A1
• 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 、 immobilised Pseudomonas cepacia lipase PSL-C I 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 72.0h， 生成 [R-(R*,R*)]-2-(2,2-二氯乙酰氨基)-3-羟基-3-(4-硝基苯基)乙基苯甲酸酯
  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

• Feitelson et al., Journal of Pharmacy and Pharmacology, 1951, vol. 3, p. 149,155
  作者：Feitelson et al.

  DOI：——

  日期：——
• Farkas; Sicher, Collection of Czechoslovak Chemical Communications, 1953, vol. 18, p. 469,477
  作者：Farkas、Sicher

  DOI：——

  日期：——
• 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.
• Diastereoisomeric propane derivatives and process for their manufacture
  申请人：PARKE DAVIS &

  公开号：US02663727A1

  公开（公告）日：1953-12-22