ethyl 5-(tert-butoxycarbonylamino)-cyclohexa-1,3-diene-1-carboxylate | 72431-26-6

• 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 5-(tert-butoxycarbonylamino)-cyclohexa-1,3-diene-1-carboxylate
• 英文别名: ethyl (5S)-5-{[(tert-butoxy)carbonyl]amino}cyclohexa-1,3-diene-1-carboxylate；ethyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexa-1,3-diene-1-carboxylate
• CAS: 72431-26-6
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: UJCYEFNBDQEBSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-(tert-butoxycarbonylamino)-cyclohexa-1,3-diene-1-carboxylate 在 copper(II) bis(trifluoromethanesulfonate) 吡啶 、 sodium azide 、 氯化铵 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 ethyl 4-acetylamino-5-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-cyclohexa-1-ene-1-carboxylate
  参考文献：
  名称：

  An iron carbonyl approach to the influenza neuraminidase inhibitor oseltamivir

  摘要：

  一种新的合成路线已成功实现，用于制备奥司他韦（一种流感神经氨酸酶抑制剂），该路线采用了阳离子铁碳基复合物，提供了一条可访问多样化类似物的替代途径。

  DOI：

  10.1039/b703295a
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 cerium(III) chloride 、 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 6.0h， 生成 ethyl 5-(tert-butoxycarbonylamino)-cyclohexa-1,3-diene-1-carboxylate
  参考文献：
  名称：

  Efficient Short Step Synthesis of Corey's Tamiflu Intermediate

  摘要：

  Corey's tamiflu intermediate was synthesized from a bicyclolactam adduct obtained by base-catalyzed Diels-Alder reaction of N-nosyl-3-hydroxy-2-pyridone with ethyl acrylate. A compound that has the same array of functional groups with the Corey's intermediate was obtained in four steps from the DA adduct in 47% overall yield. The intermediate itself was also prepared efficiently by simply changing the protective group.

  DOI：

  10.1021/ol7029646

文献信息

• Efficient Preparation of the Key Intermediate in Corey's Tamiflu Synthesis
  作者：Zhangyong Hong、Qi Cui、Jiannan Peng、Huan Hu、Zeming Chen

  DOI：10.1002/cjoc.201190025

  日期：2010.12

  A very efficient two‐step synthesis was developed to prepare the key intermediate in Corey's Tamiflu synthesis. DBU (1,8‐diazabicyclo[5.4.0] undec‐7‐ene) was used as a multifunctional catalyst for a series of reactions in a one pot procedure. The new synthesis was featured by the good availability of the starting material and the ease of the synthetic steps. This method might be practical for large

  开发了一种非常有效的两步合成法，以制备Corey的达菲合成中的关键中间体。DBU（1,8-二氮杂双环[5.4.0] undec-7-ene）被用作多功能催化剂，可在一个反应​​釜中进行一系列反应。新合成的特征是原料的良好可用性和合成步骤的简便性。该方法对于大规模制备可能是实用的。
• 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。
• An iron carbonyl approach to the influenza neuraminidase inhibitor oseltamivir
  作者：Karen M. Bromfield、Henrik Gradén、Daniel P. Hagberg、Thomas Olsson、Nina Kann

  DOI：10.1039/b703295a

  日期：——

  A novel synthetic route towards oseltamivir, an influenza neuraminidase inhibitor, has been achieved employing a cationic iron carbonyl complex, providing an alternate pathway with the potential to access diverse analogues.

  一种新的合成路线已成功实现，用于制备奥司他韦（一种流感神经氨酸酶抑制剂），该路线采用了阳离子铁碳基复合物，提供了一条可访问多样化类似物的替代途径。
• Efficient Short Step Synthesis of Corey's Tamiflu Intermediate
  作者：Nsiama Tienabe Kipassa、Hiroaki Okamura、Kengo Kina、Toshiyuki Hamada、Tetsuo Iwagawa

  DOI：10.1021/ol7029646

  日期：2008.3.1

  Corey's tamiflu intermediate was synthesized from a bicyclolactam adduct obtained by base-catalyzed Diels-Alder reaction of N-nosyl-3-hydroxy-2-pyridone with ethyl acrylate. A compound that has the same array of functional groups with the Corey's intermediate was obtained in four steps from the DA adduct in 47% overall yield. The intermediate itself was also prepared efficiently by simply changing the protective group.