(5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate | 1396317-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate
• 英文别名: ethyl (5S)-5-[bis(prop-2-enyl)amino]-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 1396317-78-4
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: FNKCTJYFOYRERN-PZORYLMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.67h， 生成
  参考文献：
  名称：

  Chromatography-free synthesis of Corey's intermediate for Tamiflu

  摘要：

  Column chromatography-free stereoselective synthesis of Corey's intermediate for Tamiflu (oseltamivir phosphate) was achieved, starting from L-glutamic acid gamma-ethyl ester. The reagents and solvents used in the reaction scheme are industrially tractable, rendering the synthesis a potential starting point for process research. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.081
• 作为产物：
  描述：

  L-谷氨酸5乙脂 在 sodium tetrahydroborate 、 甲酸 、 高氯酸 、 18-冠醚-6 、 三氧化硫吡啶 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 75.0h， 生成 (5S)-ethyl 5-(diallylamino)-2-oxocyclohex-3-ene carboxylate
  参考文献：
  名称：

  Two Approaches toward the Formal Total Synthesis of Oseltamivir Phosphate (Tamiflu): Catalytic Enantioselective Three-Component Reaction Strategy and l-Glutamic Acid Strategy

  摘要：

  Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized L-glutamic acid gamma-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to construct a six-membered ring core, after which manipulation of the functional groups and protecting groups accessed Corey's intermediate for the synthesis of oseltamivir phosphate. While the first synthesis was accomplished via four purification steps in 25.7% overall yield, albeit with moderate optical purity (76% ee), the second strategy achieved the synthesis via six purification steps in 19.8% overall yield with perfect enantiocontrol.

  DOI：

  10.1021/jo400360j

文献信息

• 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。
• COMPOUND AND METHOD FOR PRODUCING SAME, AS WELL AS METHOD FOR PRODUCING OSELTAMIVIR PHOSPHATE
  申请人：Microbial Chemistry Research Foundation

  公开号：EP3235797A1

  公开（公告）日：2017-10-25

  A compound represented by the following general formula (6), a method for producing it, and its use in the preparation of oseltamivir phosphate.

  一种由以下通式（6）表示的化合物、其制备方法以及其在制备奥司他韦磷酸盐中的用途。
• Two Approaches toward the Formal Total Synthesis of Oseltamivir Phosphate (Tamiflu): Catalytic Enantioselective Three-Component Reaction Strategy and <scp>l</scp>-Glutamic Acid Strategy
  作者：Kaliyamoorthy Alagiri、Makoto Furutachi、Kenzo Yamatsugu、Naoya Kumagai、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1021/jo400360j

  日期：2013.4.19

  Two independent formal total syntheses of oseltamivir phosphate were successfully achieved: the first utilized a copper-catalyzed asymmetric three-component reaction strategy, and the second utilized L-glutamic acid gamma-ester as a chiral source to install the correct stereochemistry. Both strategies used Dieckmann condensation to construct a six-membered ring core, after which manipulation of the functional groups and protecting groups accessed Corey's intermediate for the synthesis of oseltamivir phosphate. While the first synthesis was accomplished via four purification steps in 25.7% overall yield, albeit with moderate optical purity (76% ee), the second strategy achieved the synthesis via six purification steps in 19.8% overall yield with perfect enantiocontrol.
• JP6106452
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• EP2684866
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