2-(1-nitronaphthalen-2-yl)acetic acid | 89278-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-nitronaphthalen-2-yl)acetic acid
• 英文别名: (1-nitro-[2]naphthyl)-acetic acid；(1-Nitro-[2]naphthyl)-essigsaeure
• CAS: 89278-24-0
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: RVNRTHUGIFJSEH-UHFFFAOYSA-N

物化性质

• 熔点：
  206-207 °C(Solv: methanol (67-56-1))
• 沸点：
  436.2±25.0 °C(Predicted)
• 密度：
  1.419±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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-nitronaphthalen-2-yl)acetic acid 在 sodium hydroxide 、 镍 作用下， 生成 (1-氨基-2-萘基)乙酸
  参考文献：
  名称：

  Water-soluble Compounds with Antihemorrhagic Activity

  摘要：

  DOI：

  10.1021/ja01263a038
• 作为产物：
  描述：

  硝基萘 在 盐酸 、 sodium hydroxide 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 2-(1-nitronaphthalen-2-yl)acetic acid
  参考文献：
  名称：

  Reactions of organic anions. Part 110. Vicarious nucleophilic substitution of hydrogen in nitroarenes with .alpha.-substituted nitriles and esters. Direct .alpha.-cyanoalkylation and .alpha.-carbalkoxyalkylation of nitroarenes

  摘要：

  DOI：

  10.1021/jo00183a004

文献信息

• Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution
  作者：Michał Achmatowicz、Oliver R. Thiel、Gilles Gorins、Corinne Goldstein、Caroline Affouard、Randy Jensen、Robert D. Larsen

  DOI：10.1021/jo801131z

  日期：2008.9.1

  one-pot approach to 6-methyl-5-nitroisoquinoline (1) from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds. Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction

  描述了一种有效且可扩展的三步一锅法，该方法利用替代的亲核取代（VNS）作为关键步骤，从廉价的5-硝基异喹啉制得6-甲基-5-硝基异喹啉（1）。优化的反应条件可以应用于有限数量的其他芳族和杂芳族硝基化合物。试图了解在VNS步骤中观察到的选择性的尝试导致在VNS条件下发现了两个新的反应途径，一个导致异恶唑，另一个导致芳族硝基化合物的正式环丙烷化。
• Novel Benzoxazole 2,4-Thiazolidinediones as Potent Hypoglycemic Agents. Synthesis and Structure-Activity Relationships.
  作者：Kenji ARAKAWA、Masanori INAMASU、Mamoru MATSUMOTO、Kunihito OKUMURA、Kosuke YASUDA、Hidenori AKATSUKA、Saburo KAWANAMI、Akishige WATANABE、Koichi HOMMA、Yutaka SAIGA、Masakatsu OZEKI、Ikuo IIJIMA

  DOI：10.1248/cpb.45.1984

  日期：——

  benzoxazole 2,4-thiazolidinediones was synthesized and evaluated for hypoglycemic activity in genetically obese and diabetic yellow KK mice. 2-Arylmethyl- and 2-(heteroarylmethyl)benzoxazole derivatives showed far more potent activity than known 2,4-thiazolidinedione derivatives such as ciglitazone, troglitazone and pioglitazone. A facile synthesis of benzoxazole 2,4-thiazolidinediones was also established using

  合成了一系列新的苯并恶唑2，4-噻唑烷二酮，并评估了遗传性肥胖和糖尿病黄色KK小鼠的降血糖活性。2-芳基甲基-和2-（杂芳基甲基）苯并恶唑衍生物显示出比已知的2,4-噻唑烷二酮衍生物例如西格列酮，曲格列酮和吡格列酮强得多的活性。还使用氨基苯酚2,4-噻唑烷二酮（11）作为关键中间体，建立了苯并恶唑2,4-噻唑烷二酮的简便合成方法。描述了该系列的合成和构效关系的细节。
• Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives
  作者：Joachim Schlosser、Eugen Johannes、Melanie Zindler、Jan Lemmerhirt、Benjamin Sommer、Martin Schütt、Christian Peifer

  DOI：10.1016/j.tetlet.2014.11.015

  日期：2015.1

  We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzofuran-2-yl-methanamines. Accordingly, for the synthesis of indoles the nitro-group was first reduced and reaming these intermediates in HCl gave the corresponding indol-2-yl-methanamines. The method worked well with electron donating substituents. Limitations regarding electron withdrawing substituents are discussed. This straightforward synthetic procedure can be a useful approach to generate a variety of substituted benzofuran-2-yl-methanamine and indol-2-yl-methanamine compounds by starting from readily available phenylacetic acid derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• Mayer,F.; Oppenheimer, Chemische Berichte, 1916, vol. 49, p. 2140
  作者：Mayer,F.、Oppenheimer

  DOI：——

  日期：——
• Wislicenus; Mundinger, Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 68
  作者：Wislicenus、Mundinger

  DOI：——

  日期：——