N(pMe)phe-OEt

• 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: N(pMe)phe-OEt
• 英文别名: ethyl (4-methylbenzyl)glycinate；Ethyl 2-{[(4-methylphenyl)methyl]amino}acetate；ethyl 2-[(4-methylphenyl)methylamino]acetate
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD00968827
• 分子量: 207.272
• InChiKey: QZLMPLDNZZQWOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N(pMe)phe-OEt 在 4-二甲氨基吡啶 、 乙醇 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 ethyl 1-(4-methylbenzyl)-3-methylene-4-oxoazetidine-2-carboxylate
  参考文献：
  名称：

  PPh 3催化丙环酰胺的Uppolung环化反应合成α-亚甲基-β-内酰胺

  摘要：

  我们在这里报道了α-亚甲基-β-内酰胺的简便合成。因此，在三苯膦的催化下，回流的乙醇中的许多2-丙酰胺基乙酸酯或α-丙酰胺基酮经历了环酚环化反应，从而以高收率得到了相应的4-取代的3-亚甲基氮杂环丁烷-2-酮。

  DOI：

  10.1021/jo502265a
• 作为产物：
  描述：

  溴乙酸乙酯 、 4-甲基苄胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.08h， 以88%的产率得到N(pMe)phe-OEt
  参考文献：
  名称：

  通过肌红蛋白催化卡宾 N-H 插入选择性官能化脂肪胺

  摘要：

  工程化肌红蛋白最近因其催化各种非生物卡宾转移反应的能力而受到关注，包括通过卡宾插入 NH 键来官能化胺。然而，在这种转化的背景下，肌红蛋白和其他基于血红素蛋白的生物催化剂的范围很大程度上限于作为胺底物的苯胺衍生物和作为卡宾供体试剂的重氮乙酸乙酯。在本报告中，我们描述了一种基于工程肌红蛋白的催化剂的开发，该催化剂可用于促进各种取代苄胺和 α-重氮乙酸酯的卡宾 NH 插入反应，具有高效率（82-99% 转化率）、更高的催化转化率（高达至 7,000），并且对所需的单插入产物具有出色的化学选择性（高达 99%）。这种转化的范围可以扩展到环状脂肪胺。这些研究扩展了可用于选择性形成 CN 键的生物催化工具箱，CN 键在许多天然和合成的生物活性化合物中普遍存在。

  DOI：

  10.1055/s-0039-1690007

文献信息

• Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed-Ligand Copper(I) Complex
  作者：Stefano Brenna、G. Attilio Ardizzoia

  DOI：10.1002/ejoc.201800863

  日期：2018.7.6

  An easily prepared low‐cost copper(I) homogeneous catalyst has been investigated in carbene transfer reactions. High yields and selectivities were achieved in olefin cyclopropanation and O–H and N–H insertions.

  在卡宾转移反应中，已经研究了一种易于制备的低成本铜（I）均相催化剂。在烯烃环丙烷化以及OH和NH插入中实现了高收率和选择性。
• Palladium‐Catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of <i>N</i>‐Substituted Glycine Ethyl Esters with <i>α</i>‐(Trifluoromethyl)alkenyl Acetates
  作者：Shuaibo Zhang、Dong Li、Bangzhong Wang、Wuding Sun、Haojun Ma、Kai Di、Luyang Sun、Jinfeng Zhao、Jingping Qu、Yuhan Zhou

  DOI：10.1002/ejoc.202300593

  日期：2023.9.21

  An efficient enantioselective palladium-catalyzed trifluoromethylated allylic alkylation of N-substituted glycine ethyl esters using α-(trifluoromethyl)alkenyl acetates as trifluoromethyl-containing allyl precursors is established. A series of optically active glycine ethyl ester derivatives containing a trifluoromethylated allyl substituent are readily synthesized in good yields with superior enantioselectivities

  使用α- (三氟甲基)链烯基乙酸酯作为含三氟甲基的烯丙基前体，建立了N-取代甘氨酸乙酯的有效对映选择性钯催化三氟甲基化烯丙基烷基化。一系列含有三氟甲基化烯丙基取代基的光学活性甘氨酸乙酯衍生物很容易合成，收率良好，具有优异的对映选择性。
• MODULATORS OF TOLL-LIKE RECEPTORS
  申请人：Gilead Sciences, Inc.

  公开号：EP3210982A1

  公开（公告）日：2017-08-30

  Provided are compounds of Formula Ia: pharmaceutically acceptable salts thereof, compositions containing such compounds, and such compounds for use in the treatment of a hepatitis B viral infection.

  提供的是式 Ia 的化合物： 其药学上可接受的盐、含有此类化合物的组合物以及用于治疗乙型肝炎病毒感染的此类化合物。
• Further Studies on Nociceptin-Related Peptides:  Discovery of a New Chemical Template with Antagonist Activity on the Nociceptin Receptor
  作者：Remo Guerrini、Girolamo Calo'、Raffaella Bigoni、Anna Rizzi、Katia Varani、Geza Toth、Stefania Gessi、Eiji Hashiba、Yoshio Hashimoto、David G. Lambert、Pier Andrea Borea、Roberto Tomatis、Severo Salvadori、Domenico Regoli

  DOI：10.1021/jm990075h

  日期：2000.7.1

  Three series of nociceptin (NC)-related peptides were synthesized and their abilities (i) to bind to the NC sites expressed in mouse forebrain membranes, (ii) to inhibit the electrically evoked contraction of the mouse vas deferens, and (iii) to inhibit forskolin-stimulated cAMP accumulation in Chinese hamster ovary cells expressing the human recombinant NC receptor (CHONCR) were investigated. The compounds of the first series (a series) have an ordinary Xaa(1)-Gly(2) bond, those of the second series (b series) have a Xaa(1)Psi(CH2-NH)Gly(2) pseudopeptide bond, and those of the third series (c series) have a peptoid (Nxaa(1)-Gly(2)) structure. The affinity values measured in the binding assay and in the two functional assays with the compounds of the three series showed high levels of correlation. Thus, (I) the compounds of the a series in which Phe(1) was substituted with Tyr, Cha, or Leu acted as potent NC receptor agonists; (II) the b series compounds behaved as NC receptor antagonists in the mouse vas deferens and as full agonists in CHONCR cells with different potencies depending on the first amino acid residue, [Phe(1)Psi(CH2-NH)Gly(2)]NC(1-17)NH2 and [Phe(1)Psi(CH2-NH)Gly(2)]NC(1-13)NH2 being the most potent compounds; (III) the compounds of the third series were all inactive both as agonists and as antagonists with the exception of [Nphe(1)]NC(1-17)NH2 and [Nphe(1)]NC(1-13)NH2, which behaved as NC receptor antagonists both in the isolated tissue and in CHONCR cells (pK(B) 6.1-6.4). In conclusion, this study demonstrates that chemical requirements for NC receptor agonists are different from those of antagonists. Moreover, modifications of the steric orientation of the aromatic residue Phe(1) in the NC sequence as obtained with the pseudopeptide bond between Phe(1) and Gly(2) or with the displacement of the benzyl side chain by one atom, as in Nphe(1), lead respectively to reduction or elimination of efficacy. Indeed, in contrast to [Phe(1)Psi(CH2-NH)Gly(2)]NC(1-13)NH2 which has been reported to exhibit agonist activity in several assays involving either central or recombinant NC receptors, [Nphe(1)]NC(1-13)NH2 antagonizes the effect of NC at human recombinant NC receptors and in the mouse tail withdrawal assay.
• Intermediates for the preparation of modulators of toll-like receptors
  申请人：GILEAD SCIENCES, INC.

  公开号：EP2818469B1

  公开（公告）日：2017-02-15