1,3-diethyl 2-[(4-bromophenyl)formamido]propanedioate | 1153149-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-diethyl 2-[(4-bromophenyl)formamido]propanedioate
• 英文别名: Diethyl 2-[(4-bromobenzoyl)amino]propanedioate
• CAS: 1153149-74-6
• 化学式: C₁₄H₁₆BrNO₅
• 分子量: 358.189
• InChiKey: LWFVVMUGPXLJDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1,3-diethyl 2-[(4-bromophenyl)formamido]propanedioate 在 sodium ethanolate 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 乙醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs

  摘要：

  Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t) ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 mu M in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.077
• 作为产物：
  描述：

  氨基丙二酸二乙酯 、 4-溴苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 1,3-diethyl 2-[(4-bromophenyl)formamido]propanedioate
  参考文献：
  名称：

  Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs

  摘要：

  Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t) ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 mu M in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.077

文献信息

• Reaction of Tetramethyl Ethynyldiphosphonate with Diethyl 2-Amidomalonates
  作者：D. M. Egorov、A. A. Petrosyan、Yu. L. Piterskaya、N. I. Svintsitskaya、A. V. Dogadina

  DOI：10.1134/s1070363218110294

  日期：2018.11

  Stereoselective reaction of tetramethyl ethynyldiphosphonate with diethyl 2-amidomalonates yielded Z-vinyldiphosphonates, namely Z-2-[1,2-bis(dimethoxyphosphoryl)-2-alkyl(aryl)amidovinyl]malonic acid diethyl esters. A possibility of cyclization of the amidomalonate fragment of the obtained alkenes with the formation of an oxazole-substituted Z-vinyldiphosphonate was shown.

  乙炔基二膦酸四甲酯与2-氨基苯甲酸二乙酯的立体选择反应产生Z-乙烯基二膦酸酯，即Z -2- [1,2-双（二甲氧基磷酰基）-2-烷基（芳基）氨基乙烯基]丙二酸二乙酯。显示了形成的恶唑取代的Z-乙烯基二膦酸酯可能环化所获得的烯烃的酰胺基丙二酸酯片段。
• Electrochemical Synthesis of Unnatural Amino Acids via Anodic Decarboxylation of <i>N</i>-Acetylamino Malonic Acid Derivatives
  作者：Olesja Koleda、Katrina Prane、Edgars Suna

  DOI：10.1021/acs.orglett.3c02687

  日期：2023.11.10

  α-disubstituted cyclic amino acid derivatives in medicinal chemistry urges for analogue design with improved pharmacokinetic properties. Herein, we disclose an electrochemical approach toward unnatural THF- and THP-containing amino acid derivatives that relies on anodic decarboxylation-intramolecular etherification of inexpensive and readily available N-acetylamino malonic acid monoesters under Hofer–Moest

  α,α-二取代环状氨基酸衍生物在药物化学中的广泛应用迫切需要具有改进的药代动力学特性的类似物设计。在此，我们公开了一种针对非天然含THF和THP的氨基酸衍生物的电化学方法，该方法依赖于廉价且容易获得的N-乙酰氨基丙二酸单酯在Hofer-Moest反应条件下的阳极脱羧-分子内醚化。脱羧环化在恒定电流条件下在未分裂的细胞中在水性介质中进行，无需添加任何碱。在组织蛋白酶 K 抑制剂 balicatib 中，用含 THP 的氨基酸支架成功生物等排取代 1-氨基环己烷-1-羧酸亚基，有助于降低亲脂性，同时保留低纳摩尔酶抑制效力和相当的微粒体稳定性。
• Structurally Divergent Synthesis of Azetidines, 5,6‐Dihydro‐1,3‐oxazines and 2,3‐Dihydro‐1,4‐oxazines through Palladium‐Catalyzed Tandem Allylic Substitution Reaction
  作者：Ru‐Fang Meng、Yu‐Juan Kong、Xiao‐Yan Wu、Huan Zhang、Wei Wang、Wen‐Jie Liang、Lan Zheng、Chenxiang Lin、Wei Su、Jun‐An Xiao

  DOI：10.1002/cjoc.202400533

  日期：2024.11.15

  A regiodivergent synthesis of azetidines, 5,6-dihydro-1,3-oxazines and 2,3-dihydro-1,4-oxazines has been achieved through palladium-catalyzed tandem allylic substitution reaction. This protocol provides a variety of heterocycles in satisfactory yields with good to excellent regioselectivities under mild reaction conditions.

  氮杂齐胺、5,6-二氢-1,3-恶嗪和 2,3-二氢-1,4-恶嗪的区域差异合成是通过钯催化的串联烯丙基取代反应实现的。该方案以令人满意的产量提供了多种杂环，在温和的反应条件下具有良好到优异的区域选择性。