ethyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-oxohex-2-enoate | 1160175-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-oxohex-2-enoate
• 英文别名: ethyl (E,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohex-2-enoate
• CAS: 1160175-56-3
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: GHOXGTQYQMZPQH-FLOXNTQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-oxohex-2-enoate 、 (三氟甲基)三甲基硅烷 在 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.83h， 以24%的产率得到ethyl (4S,5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-4-(trifluoromethyl)hex-2-enoate
  参考文献：
  名称：

  Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation

  摘要：

  A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.

  DOI：

  10.1021/jo9005602
• 作为产物：
  描述：

  乙醛酸乙酯 、 dimethyl (S)-3-[N-(tert-butoxycarbonyl)amino]-2-oxobutylphosphonate 在 三乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以31%的产率得到ethyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-oxohex-2-enoate
  参考文献：
  名称：

  Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation

  摘要：

  A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.

  DOI：

  10.1021/jo9005602

文献信息

• Macrocyclic broad spectrum antibiotics
  申请人：RQX PHARMACEUTICALS, INC.

  公开号：US10392422B2

  公开（公告）日：2019-08-27

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供的是抗菌化合物，其中的化合物在某些实施方案中具有广谱生物活性。在不同的实施方案中，这些化合物通过抑制细菌 1 型信号肽酶（SpsB）发挥作用，SpsB 是细菌中的一种重要蛋白质。还提供了使用本文所述化合物进行治疗的药物组合物和方法。
• MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS
  申请人：RQX PHARMACEUTICALS, INC.

  公开号：US20170088582A1

  公开（公告）日：2017-03-30

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.
• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2015179441A2

  公开（公告）日：2015-11-26

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.
• Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation
  作者：Kazuya Kobayashi、Tetsuo Narumi、Shinya Oishi、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1021/jo9005602

  日期：2009.6.19

  A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.