ethyl 2-((2-bromophenyl)amino)acetate | 2521-90-6

• 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 2-((2-bromophenyl)amino)acetate
• 英文别名: N-(2-Bromophenyl)glycine ethyl ester；ethyl 2-(2-bromoanilino)acetate
• CAS: 2521-90-6
• 化学式: C₁₀H₁₂BrNO₂
• mdl: MFCD11153108
• 分子量: 258.115
• InChiKey: XNAIKMPZNSDUJS-UHFFFAOYSA-N

物化性质

• 沸点：
  322.0±22.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  ethyl 2-((2-bromophenyl)amino)acetate 在 盐酸 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 N-(2-Phosphonophenyl)glycine
  参考文献：
  名称：

  Exploration of N-phosphonoalkyl-, N-phosphonoalkenyl-, and N-(phosphonoalkyl)phenyl-spaced .alpha.-amino acids as competitive N-methyl-D-aspartic acid antagonists

  摘要：

  A series of N-substituted alpha-amino acids containing terminal phosphonic acid groups has been synthesized as potential N-methyl-D-aspartate (NMDA) receptor antagonists. NMDA receptor affinity was determined by displacement of a known ligand ([H-3]CPP) from crude rat brain synaptic membranes; an antagonist action was demonstrated by the inhibition of glutamate-induced accumulation of [Ca-45(2+)] in cultured rat cortical neurons. Receptor affinity was significantly correlated with antagonist activity (Figure 1). Moderate affinity (IC50 = 1-2-mu-M) was retained for analogues (31 and 32, Table 1; and 59 and 66, Table II) with reduced flexibility in their phosphonate side chains and is consistent with entropy playing a role in determining receptor affinity. Modeling studies suggest a folded conformation that brings the distal phosphonic acid group into close proximity with the alpha-carboxylate is required for binding. Each of the active analogues possess entropy-limiting features (double bonds, phenyl rings) in their side chains that allows the superposition of their key NH2, alpha-COOH, and distal PO3H2 groups with those of known competitive antagonists. Affinity decreased for analogues with alpha-carbon substitution, presumably because the alpha-substituent inhibits the folding of these structures into a bioactive conformation and occupies receptor-excluded volume. A complete description of the NMDA antagonist pharmacophore model is provided in a companion paper. 1

  DOI：

  10.1021/jm00086a005
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 alkali bromide 、 水 、 溴 作用下， 生成 ethyl 2-((2-bromophenyl)amino)acetate
  参考文献：
  名称：

  Schoeller; Schrauth; Goldacker, Chemische Berichte, 1911, vol. 44, p. 1307

  摘要：

  DOI：

文献信息

• Arylamino containing hydroxamic acids as potent urease inhibitors for the treatment of Helicobacter pylori infection
  作者：Qi Liu、Wei-Kang Shi、Shen-Zhen Ren、Wei-Wei Ni、Wei-Yi Li、Hui-Min Chen、Pei Liu、Jing Yuan、Xiao-Su He、Jia-Jia Liu、Peng Cao、Pu-Zhen Yang、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2018.06.065

  日期：2018.8

  evaluated as anti-virulence agents for the treatment of gastritis and gastric ulcer caused by Helicobacter pylori. In vitro enzyme-based screen together with in vivo assays and structure−activity relationship (SAR) studies led to the discovery of three potent urease inhibitors 3-(3,5-dichlorophenylamino)N-hydroxypropanamide (3a), 3-(2-chlorophenylamino)N-hydroxypropanamide (3d) and 3-(2,4-dichlorophenylam

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• Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles
  作者：Jialin Xie、Yuanqiong Huang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.7b02767

  日期：2017.11.17

  An atom-economical method for accessing tetrasubstituted 4,5-biscarbonylimidazoles by reaction between glycine derivatives and 5-alkoxyoxazoles is reported. The method, which involves a copper-catalyzed aerobic oxidative [2 + 3] cyclization/aromatization cascade process, starts from readily available and inexpensive materials, uses molecular oxygen as a co-oxidant, and has a broad substrate scope.

  报道了通过甘氨酸衍生物和5-烷氧基恶唑之间的反应获得四取代的4，5-双羰基咪唑的原子经济方法。该方法涉及铜催化的好氧氧化[2 + 3]环化/芳香化反应级联过程，从容易获得且廉价的材料开始，使用分子氧作为助氧化剂，具有广泛的底物范围。
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  作者：Abdel-Moneim Abu-Elfotoh

  DOI：10.1016/j.tetlet.2017.10.062

  日期：2017.12

  A water-soluble Ru(II)-hm-pheox complex was efficiently catalyzed NH insertion of EDA with a broad class of amine derivatives in water/ether biphasic medium to deliver the biologically active precursors α-aminoester products with excellent yields (up to >99%). The products were separated by decantation and the catalyst was washed and reused several times (at least 8 times) without any specific loss

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• Intramolecular Mizoroki–Heck Reaction of 2-Thiosubstituted Acrylates for the Synthesis of 3-Substituted Benzo[b]thiophene-2-carboxylates
  作者：Young-Dae Gong、Se Kwak、Su-Jeong Lim、Hyun-Jeong Yoo、Ji-Eun Ha

  DOI：10.1055/s-0035-1562613

  日期：——

  condition. 3-Substituted 2-(phenylthio)acrylates prepared from aldol condensation using titanium tetrachloride were employed to synthesize benzo[b]thiophenes. The acrylates containing aryls and alkyls generated the desired benzo[b]thiophenes in reasonable yields under the optimized Heck condition, but acrylates having heteroaryls gave the desired products in poor yields or no products under the condition

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• Exploiting and Engineering Neuroglobin for Catalyzing Carbene N–H Insertions and the Formation of Quinoxalinones
  作者：Li-Juan Sun、Huamin Wang、Jia-Kun Xu、Shu-Qin Gao、Ge-Bo Wen、Ying-Wu Lin

  DOI：10.1021/acs.inorgchem.3c02855

  日期：2023.10.9

  1-aminopyrene. Moreover, for o-phenylenediamine derivatives, they underwent two cycles of N–H insertions, followed by cyclization to form quinoxalinones, as confirmed by the X-ray crystal structures. This study suggests that Ngb can be designed into a functional carbene transferase for efficiently catalyzing carbene N–H insertion reactions with a range of substrates. It also represents the first example of the

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