ethyl 2-amino-2-(naphthalen-2-yl)acetate | 110470-27-4

• 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-amino-2-(naphthalen-2-yl)acetate
• 英文别名: ethyl 2-amino-2-naphthalen-2-ylacetate
• CAS: 110470-27-4；110470-41-2；110470-42-3
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD02662791
• 分子量: 229.279
• InChiKey: UTEANATWINVRDV-UHFFFAOYSA-N

物化性质

• 沸点：
  360.7±22.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-2-(naphthalen-2-yl)acetate 在 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 2-(Boc-氨基)-2-(2-萘)乙酸
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002
• 作为产物：
  描述：

  氨基(萘-2-基)乙酸 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以93%的产率得到ethyl 2-amino-2-(naphthalen-2-yl)acetate
  参考文献：
  名称：

  催化瞬态导向基团促进的游离氨基酯的位点选择性γ-C（sp3）-H和γ-C（sp2）-H芳基化

  摘要：

  首次使用选择性Pd II催化的游离氨基酯的γ-C（sp 3）-H和γ-C（sp 2）-H芳基化反应，使用市售的催化瞬态导向基团。各种游离的氨基酯，包括α-氨基酯和β-氨基酯，氨基单酯和氨基双酯，都可以与多种简单的碘化芳基和杂芳基试剂反应。

  DOI：

  10.1002/chem.201802465

文献信息

• A Versatile Approach to CF₃-Containing 2-Pyrrolidones by Tandem Michael Addition-Cyclization: Exemplification in the Synthesis of Amidine Class BACE1 Inhibitors
  作者：Natalia Mateu、Myriam Ciordia、Oscar Delgado、María Sánchez-Roselló、Andrés A. Trabanco、Michiel Van Gool、Gary Tresadern、Laura Pérez-Benito、Santos Fustero

  DOI：10.1002/chem.201501662

  日期：2015.8.10

  The synthesis of new fluorinated pyrrolidones starting from unprotected amino esters and amino nitriles through a Michael addition–lactamization sequence is described. The resulting CF3‐containing building blocks, bearing a quaternary stereogenic center adjacent to the fluorinated group, have been converted into amino pyrrolidines that display potent β‐secretase 1 (BACE1) inhibitory activity. This

  描述了通过未加保护的氨基酯和氨基腈通过迈克尔加成-内酰胺化序列合成新的氟化吡咯烷酮。所得的含CF 3的结构单元带有一个与氟化基团相邻的四级立体异构中心，已被转化为氨基吡咯烷，具有强大的β-分泌酶1（BACE1）抑制活性。这项工作构成了选择性氟化的一个实例，作为在药物发现中调节先导化合物的物理化学和生物学特性的有效策略。
• 2-Aryl-2-nitroacetates as Central Precursors to Aryl Nitromethanes, α-Ketoesters, and α-Amino Acids
  作者：Alison E. Metz、Marisa C. Kozlowski

  DOI：10.1021/jo302071s

  日期：2013.1.18

  Nitroarylacetates are useful small molecular building blocks that act as precursors to alpha-ketoesters and aryl nitromethanes as well as alpha-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions for decarboxylation are discussed for substrates with neutral and electron-poor aryl groups versus electron-rich aryl groups. For formation of the alpha-ketoesters, new mild conditions for the Nef disproportionation were identified.
• Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides
  作者：Pranjal K. Baruah、Jason Dinsmore、Amber M. King、Christophe Salomé、Marc De Ryck、Rafal Kaminski、Laurent Provins、Harold Kohn

  DOI：10.1016/j.bmc.2012.04.002

  日期：2012.6

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.
• Site-Selective γ-C(sp³)−H and γ-C(sp²)−H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group
  作者：Hua Lin、Chao Wang、Thomas D. Bannister、Theodore M. Kamenecka

  DOI：10.1002/chem.201802465

  日期：2018.7.5

  The first selective PdII‐catalysed γ‐C(sp3)−H and γ‐C(sp2)−H arylation of free amino esters using a commercially available catalytic transient directing group. A variety of free amino esters, including α‐amino esters and β‐amino esters, amino monoesters and amino bis‐esters, are shown to react with a diverse range of simple aryl and heteroaryl iodide reagents.

  首次使用选择性Pd II催化的游离氨基酯的γ-C（sp 3）-H和γ-C（sp 2）-H芳基化反应，使用市售的催化瞬态导向基团。各种游离的氨基酯，包括α-氨基酯和β-氨基酯，氨基单酯和氨基双酯，都可以与多种简单的碘化芳基和杂芳基试剂反应。