2-氰基-5-甲氧基苯甲酸甲酯 | 127510-95-6

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-5-甲氧基苯甲酸甲酯
• 英文名称: 2-cyano-5-methoxybenzoic acid methyl ester
• 英文别名: methyl 2-cyano-5-methoxybenzoate
• CAS: 127510-95-6
• 化学式: C₁₀H₉NO₃
• mdl: MFCD09800435
• 分子量: 191.186
• InChiKey: YIRZMMZVHCFIAK-UHFFFAOYSA-N

物化性质

• 熔点：
  74-77 °C
• 沸点：
  340.2±27.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  2-氰基-5-甲氧基苯甲酸甲酯 在 氨 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.17h， 生成 Ethyl 2-cyano-2-(1-cyano-5-methoxy-2-methyl-3-oxoisoindol-1-yl)acetate
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲酸甲酯 、 氰化锌 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 2-氰基-5-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  WO2007/56210

  摘要：

  公开号：

文献信息

• Synthesis of methyl-, fluoro-, and chloro-substituted 6-hydroxyisoindolin-1-ones
  作者：James J. Powers、David A. Favor、Trent Rankin、Rashmi Sharma、Chetan Pandit、Azhwarsamy Jeganathan、Samarendra N. Maiti

  DOI：10.1016/j.tetlet.2008.12.099

  日期：2009.3

  The synthesis of a series of methyl-, fluoro-, and chloro-substituted 6-hydroxyisoindolin-1-ones is described.

  描述了一系列甲基，氟和氯取代的6-羟基异吲哚啉-1-酮的合成。
• <i>Cine</i>-Substitutions at Five-Membered Hetarenes Enabled by Sulfonium Salts
  作者：Florian Berger、Eva Maria Alvarez、Nils Frank、Kostiantyn Bohdan、Mykhailo Kondratiuk、Luca Torkowski、Pascal S. Engl、Joana Barletta、Tobias Ritter

  DOI：10.1021/acs.orglett.0c02067

  日期：2020.7.17

  We report a nucleophilic substitution reaction of five-membered hetarylsulfonium salts that results in a change of the substitution pattern on the arene. The products of these cine-substitutions are hard to access synthetically otherwise. The sulfonium salts that serve as starting materials are generated by a highly site-selective C–H functionalization reaction.

  我们报告了五元杂芳基salts盐的亲核取代反应，导致芳烃上的取代模式的变化。这些电影替代品的产品很难通过其他方式综合获得。用作起始原料的sulf盐是通过高度位点选择性的CH官能化反应生成的。
• Diphenylmethane Derivatives as Inhibitors of Leukotriene Biosynthesis
  申请人：Armstrong Helen M.

  公开号：US20090258885A1

  公开（公告）日：2009-10-15

  The instant invention provides compounds of Formula I which are 5-lipoxygenase activating protein inhibitors. Compounds of Formula I are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.

  本发明提供了公式I的化合物，这些化合物是5-脂氧合酶活化蛋白抑制剂。公式I的化合物可用作抗动脉粥样硬化、抗哮喘、抗过敏、抗炎和细胞保护剂。
• Ethyl Cyanoacetate: A New Cyanating Agent for the Palladium-Catalyzed Cyanation of Aryl Halides
  作者：Shuyan Zheng、Chunhui Yu、Zhengwu Shen

  DOI：10.1021/ol3014914

  日期：2012.7.20

  A new Pd-catalyzed cyanation reaction has been discovered using ethyl cyanoacetate as the cyanating reagent. A variety of electron-rich and electron-deficient aryl halides were efficiently converted into their corresponding nitriles in good to excellent yields.
• WO2008/20306
  申请人：——

  公开号：——

  公开（公告）日：——