ethyl 3-acetamido-4-bromo-5-(tert-butoxycarbonylamino)cyclohex-1-ene-1-carboxylate | 891862-22-9

• 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: ethyl 3-acetamido-4-bromo-5-(tert-butoxycarbonylamino)cyclohex-1-ene-1-carboxylate
• 英文别名: ethyl (3S,4S,5S)-3-acetamido-4-bromo-5-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexene-1-carboxylate
• CAS: 891862-22-9
• 化学式: C₁₆H₂₅BrN₂O₅
• 分子量: 405.289
• InChiKey: PXQXOUPBVNNCJE-RWMBFGLXSA-N

物化性质

• 沸点：
  549.2±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-acetamido-4-bromo-5-(tert-butoxycarbonylamino)cyclohex-1-ene-1-carboxylate 在 四丁基溴化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 0.17h， 以82%的产率得到(1S,5S,6R)-ethyl 7-acetyl-5-(tert-butoxycarbonylamino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate
  参考文献：
  名称：

  A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid

  摘要：

  A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; (4) good overall yield (ca. 30%, still not completely optimized); and (5) scalability.

  DOI：

  10.1021/ja0616433
• 作为产物：
  描述：

  (S)-ethyl 5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-dienecarboxylate 、 N-溴代乙酰胺 在 溴化锡 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 以71%的产率得到ethyl 3-acetamido-4-bromo-5-(tert-butoxycarbonylamino)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  A Short Enantioselective Pathway for the Synthesis of the Anti-Influenza Neuramidase Inhibitor Oseltamivir from 1,3-Butadiene and Acrylic Acid

  摘要：

  A short synthetic pathway has been developed for the synthesis of oseltamivir (1) or the enantiomer (ent-1). The intermediates and conditions for this process are summarized in Scheme 1. The synthesis provides a number of advantages: (1) use of inexpensive and abundant starting materials; (2) complete enantio-, regio-, and diastereocontrol; (3) avoidance of explosive, azide-type intermediates; (4) good overall yield (ca. 30%, still not completely optimized); and (5) scalability.

  DOI：

  10.1021/ja0616433

文献信息

• INTERMEDIATE COMPOUNDS OF TAMIFLU, METHODS OF PREPARATION AND USES THEREOF
  申请人：Ma Dawei

  公开号：US20140221662A1

  公开（公告）日：2014-08-07

  Chiral amino compounds, methods of preparation and uses thereof. Tamiflu can be obtained from the said compounds. Multi-substituted chiral tetrahydropyrrolyl amine which can be used as intermediate compounds of medicament can also be produced by the said compounds.

  手性氨基化合物，其制备方法及用途。 好病毒药物达菌素可以从这些化合物中获得。 这些化合物还可以制备用作药物中间体的多取代手性四氢吡咯基胺。
• Compound, Method for Producing the Same, and Method for Producing Oseltamivir Phosphate
  申请人：Microbial Chemistry Research Foundation

  公开号：US20140046087A1

  公开（公告）日：2014-02-13

  A compound represented by the following general formula (1), and a method for producing the compound represented by the general formula (1), the method comprising: reacting together a compound represented by the following general formula (2), a compound represented by the following general formula (3), and a compound represented by the following general formula (4): wherein R 1 represents any of a protective group of a carboxyl group, and a hydrogen atom, R 2 and R 3 each independently represent any of a protective group of an amino group, and a hydrogen atom, and R 4 represents any of a protective group of a carboxyl group, and a hydrogen atom.

  以下为通用公式（1）所代表的化合物，以及制备通用公式（1）所代表的化合物的方法，该方法包括：将以下通用公式（2）所代表的化合物、以下通用公式（3）所代表的化合物和以下通用公式（4）所代表的化合物反应在一起：其中，R1表示羧基的保护基中的任意一种，或氢原子；R2和R3各自独立地表示氨基的保护基中的任意一种，或氢原子；R4表示羧基的保护基中的任意一种，或氢原子。
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