2-甲氧基羰基氨基-5-硝基苯甲酸甲酯 | 377725-39-8

• 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-甲氧基羰基氨基-5-硝基苯甲酸甲酯
• 英文名称: 2-methoxycarbonylamino-5-nitrobenzoic acid methyl ester
• 英文别名: methyl 2-(methoxycarbonylamino)-5-nitrobenzoate
• CAS: 377725-39-8
• 化学式: C₁₀H₁₀N₂O₆
• 分子量: 254.199
• InChiKey: FRTNUFIURVPYFU-UHFFFAOYSA-N

物化性质

• 沸点：
  359.1±32.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-甲氧基羰基氨基-5-硝基苯甲酸甲酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以100%的产率得到5-amino-2-methoxycarbonylaminobenzoic acid methyl ester
  参考文献：
  名称：

  [EN] SMALL MOLECULES FOR INHIBITING MALE FERTILITY
  [FR] PETITES MOLÉCULES POUR INHIBER LA FERTILITÉ MÂLE

  摘要：

  提供适用于提供男性避孕的化合物，用于识别此类化合物的测定方法，以及使用这些化合物提供避孕的方法。在一个实施例中，这里描述的化合物模拟抗EPPIN抗体与EPPIN的结合，从而抑制人类和其他灵长类动物的精子前向运动。在另一个实施例中，这里描述的化合物抑制或增强EPPIN-精浆蛋白结合，并抑制精子的前向运动。这里描述的测定方法识别抑制精子运动的化合物，并可以通过使用标记的重组EPPIN和精浆蛋白以高通量方式进行。这些化合物可以用于口服或经皮组合物，以暂时和可逆地抑制男性生育能力。它们也可以用于与避孕套、避孕膜和杀精子凝胶等杀精子组合物一起使用，或替代它们。

  公开号：

  WO2015138919A1
• 作为产物：
  描述：

  2-氨基-5-硝基苯甲酸 在 硫酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 7.5h， 生成 2-甲氧基羰基氨基-5-硝基苯甲酸甲酯
  参考文献：
  名称：

  Effect of the amino versus the acylamino substituent on the product isomer distribution in the methanolysis of 5-(substituted)-2-[(methylsulfonyl)oxy]isoindole-1,3-diones

  摘要：

  The effect of the NH2 versus the CH3CONH and PhCH2CONH substituents at the 5-position in 5-(substituted)-2-[(methylsulfonyl)oxy]isoindole- 1,3-diones, on the product isomer distribution resulting from methanolysis, was investigated both experimentally and at the RHF/3-2 1 G(*), RHF/6-31 + G(*) and B3LYP/6-31 + G(*) levels of theory. The influence of solvent on the transition structure was investigated using the Onsager SCRF model. The influence of these substituents on the transition state (TS) leading to tetrahedral intermediate was studied. The 5-amino (para to C-1) function makes the C-1 carbonyl carbon more electron-rich and less reactive toward nucleophilic attack. A predominance of the isomer formed from initial nucleophilic attack at C-3 is observed for the NH2 substituent, whereas this selectivity is greatly reduced for the acylamino substituents. Examination of the LUMO from ab initio calculations performed on the starting materials at the RBF/6-31G(*) level give a good qualitative description of the regio selectivity observed from experiment. Calculated AE, values of this initial reaction step give a qualitative description of the experimentally observed regioselectivity in agreement with the LUMO model and resonance argument. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00827-4

文献信息

• Hofmann-Type Rearrangement of Imides by in Situ Generation of Imide-Hypervalent Iodines(III) from Iodoarenes
  作者：Katsuhiko Moriyama、Kazuma Ishida、Hideo Togo

  DOI：10.1021/ol300028j

  日期：2012.2.3

  The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted

  使用由PhI，m -CPBA和TsOH·H 2 O原位生成的高价碘（III）试剂对芳族和脂族酰亚胺进行霍夫曼型重排，可在醇中存在碱的情况下进行，以提供邻氨基苯甲酸衍生物和氨基酸衍生物分别高收率。这通过经由醇解之后是霍夫曼一个串联反应反应进行重排由酰亚胺-λ的形成促进了3 -iodane中间。
• Effect of catalytic alkali metal bromide on Hofmann-type rearrangement of imides
  作者：Katsuhiko Moriyama、Kazuma Ishida、Hideo Togo

  DOI：10.1039/c2cc33914e

  日期：——

  The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.

  使用KBr作为催化剂的芳族和脂族酰亚胺的霍夫曼型重排进行以提供芳族和脂族氨基酸衍生物。我们还开发了这种方法合成加巴喷丁的新合成途径。
• Oxidative Cleavage of C2–C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates
  作者：Nandkishor Karade、Amit Kalbandhe、Ashish Kavale、Prerana Thorat

  DOI：10.1055/s-0035-1560990

  日期：——

  On reaction with (diacetoxyiodo)benzene, isatin and N-acetyl isatin undergo the oxidative C2-C3 bond cleavage to form carbamates of alkyl anthranilates and alkyl 2-acetamidobenzoate, respectively.
• SMALL MOLECULES FOR INHIBITING MALE FERTILITY
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20170057934A1

  公开（公告）日：2017-03-02

  Compounds suitable for use in providing male contraception, an assay method for identifying such compounds, and methods of providing contraception using the compounds, are provided. In one embodiment, the compounds described herein mimic the binding of anti-EPPIN antibodies to EPPIN, and thus inhibit the forward motility of sperm in humans and other primates. In another embodiment, the compounds described herein inhibit or enhance EPPIN-semenogelin binding, and inhibit forward motility of sperm. The assays described herein identify compounds which inhibit sperm motility, and can be carried out in a high throughput manner, using labeled recombinant EPPIN and semenogelin. The compounds can be used in oral or transdermal compositions to temporarily and reversibly inhibit male fertility. They can also be used in addition to, or in place of, spermicides in spermicidal compositions, such as those used in conjunction with condoms, diaphragms, and spermicidal jellies.