methyl 3-nitro-N⁴-propylaminobenzoate | 128429-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-nitro-N⁴-propylaminobenzoate
• 英文别名: methyl 3-nitro-4-(propylamino)benzoate
• CAS: 128429-03-8
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: YNIMKYLYDRQUQA-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C
• 沸点：
  384.1±32.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922499990

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 3-nitro-4-(propylamino)benzoate
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 3-nitro-4-(propylamino)benzoate
CAS number: 128429-03-8

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H14N2O4
Molecular weight: 238.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  methyl 3-nitro-N⁴-propylaminobenzoate 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N³-(N-propyl)-acetamido-7-(N-propyl)-formamido-N¹⁰-propylisoalloxazine
  参考文献：
  名称：

  Synthesis of bifunctionalised flavins for incorporation into well defined redox systems

  摘要：

  The syntheses of isoalloxazines functionalised at C-7 and N-3, suitable for two point parallel face attachment to gold in the construction of flavin-gold electrodes, are described.

  DOI：

  10.1016/s0040-4020(01)81374-0
• 作为产物：
  描述：

  4-氟-3-硝基苯甲酸 在 硫酸 作用下， 以 乙腈 为溶剂， 生成 methyl 3-nitro-N⁴-propylaminobenzoate
  参考文献：
  名称：

  A concise synthesis of 2-(2-aminothiophene)-benzimidazoles by one-pot multicomponent reaction

  摘要：

  通过在改进的 Gewald 多组分反应中利用 2-氰甲基苯并咪唑，实现了 2-氨基噻吩连接的苯并咪唑的一锅法合成。该反应的合成策略是在回流条件下用含有活性亚甲基的醛和硫粉处理2-(氰甲基)-苯并咪唑。该多组分反应通过 2-(氰甲基)-苯并咪唑与醛的 Knoevenagel 缩合进行，生成 α,β-不饱和腈，然后在碱性条件下与分子硫环化，得到生物相关的 2-(2-氨基噻吩)-苯并咪唑。产量。

  DOI：

  10.1039/c3ra41545g

文献信息

• 2-aminobenzimidazoles for leishmaniasis: From initial hit discovery to in vivo profiling
  作者：Rafael Augusto Alves Ferreira、Celso de Oliveira Rezende Junior、Pablo David Grigol Martinez、Paul John Koovits、Bruna Miranda Soares、Leonardo L. G. Ferreira、Simone Michelan-Duarte、Rafael Consolin Chelucci、Adriano D. Andricopulo、Mariana K. Galuppo、Silvia R. B. Uliana、An Matheeussen、Guy Caljon、Louis Maes、Simon Campbell、Jadel M. Kratz、Charles E. Mowbray、Luiz Carlos Dias

  DOI：10.1371/journal.pntd.0009196

  日期：——

  treatment regimens. A library of 1.8 million compounds, from which the hits reported here are publicly available, was screened against Leishmania infantum as part of an optimization program; a compound was found with a 2-aminobenzimidazole functionality presenting moderate potency, low metabolic stability and high lipophilicity. Several rounds of synthesis were performed to incorporate chemical groups

  利什曼病是一种主要的传染病，每年有成千上万的新病例，死亡人数超过20,000。当前用于治疗这种威胁生命的感染的药物具有一些缺点，例如毒性和长期的治疗方案。作为优化计划的一部分，针对婴儿利什曼原虫筛选了180万种化合物的库，可以从此处公开报道点击率。发现具有2-氨基苯并咪唑官能度的化合物具有中等效力，低代谢稳定性和高亲脂性。进行了几轮合成以结合能够降低亲脂性和清除率的化学基团，从而鉴定出对不同寄生虫菌株具有活性并具有改进的体外特性的化合物。这项优化计划的结果是，为了预期体内评估，进一步测试了一组化合物。用化合物29（婴儿乳IC50：4.1μM）和39（婴儿乳IC50：0.5μM）在急性婴儿VL小鼠模型中进行了体内测试，结果显示暴露不良且缺乏功效的问题，尽管具有良好的体外效能。
• Copper catalyzed aerobic oxidative cyclization and ketonization: one pot synthesis of benzoimidazo[1,2-a]imidazolones
  作者：Manikandan Selvaraju、Tzuen-Yang Ye、Chia-Hsin Li、Pei-Heng Ho、Chung-Ming Sun

  DOI：10.1039/c6cc01828a

  日期：——

  A highly efficient synthesis of benzoimidazo[1,2-a]imidazolone through a novel oxidative 5-exo-dig cyclization-ketonization cascade of 2-aminobenzimidazole, aldehyde and terminal alkyne has been explored under aerobic conditions.

  在有氧条件下，通过2-氨基苯并咪唑，醛和末端炔的新型5 - exo -dig环化-酮化级联反应，高效合成了苯并咪唑并[1,2- a ]咪唑酮。
• Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization
  作者：Po-Hsin Eric Yao、Sunil Kumar、Yu-Li Liu、Chiu-Ping Fang、Chia-Chen Liu、Chung-Ming Sun

  DOI：10.1021/acscombsci.7b00004

  日期：2017.4.10

  Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine

  N-（2-氨基苯基）-2-氰基乙酰胺通过一锅三步顺序反应以优异的收率实现了香豆素连接的苯并咪唑的多样性导向合成。氰基乙酰胺的原位分子内环化得到苯并咪唑，随后使2-氰基甲基苯并咪唑与三乙胺促进的水杨醛进行Knoevenagel缩合反应以达到目标化合物。的重要中间体，2-（2-亚氨基-2- ħ -苯并吡喃-3-基）-1 ħ -苯并咪唑用X射线分析，并进一步水解为2-（香豆素-3-基）苯并咪唑在酸性条件下。在合成的化合物中，发现有一些是猪肾d-氨基酸氧化酶（pk DAO）。
• Modulating catalytic activity of a modified flavin analogue <i>via</i> judicially positioned metal ion toward aerobic sulphoxidation
  作者：M. S. S. Vinod Mouli、Ashutosh Kumar Mishra

  DOI：10.1039/d1ra06558k

  日期：——

  describes the synthesis, spectroscopic and crystallographic characterization of a cadmium complex of 10-propoylisoalloxazine-7-carboxylic acid (Flc-Cd). Catalytic activity of Flc-Cd towards aerobic sulphoxidation reaction was investigated in the presence of L-ascorbic acid as the reducing agent. Notably the neutral un-metalated flavin analogue did not show any significant catalytic activity. The design

  这份手稿描述了 10-丙酰异恶嗪-7-羧酸 ( Flc-Cd ) 的镉络合物的合成、光谱和晶体学表征。在L-抗坏血酸作为还原剂存在的情况下，研究了Flc-Cd对好氧硫化氧化反应的催化活性。值得注意的是，中性非金属化黄素类似物没有表现出任何显着的催化活性。Flc的设计策略在不损害催化位点的情况下提供金属中心与黄素核心的紧密接近，从而与非金属化 Flc相比有助于产物形成. 在使用不对称硫化物的情况下也观察到较小的对映选择性；表明手性L-抗坏血酸可能参与中间体的形成。
• Synthesis, characterization and photophysical studies of the flavopeptide conjugates as model for the covalently linked flavoenzymes
  作者：M S S Vinod Mouli、Ashutosh Kumar Mishra

  DOI：10.1007/s12039-022-02050-4

  日期：2022.6

  Here, we have demonstrated an easy and efficient synthetic route for the synthesis of the flavo-peptide conjugates as model for the naturally occurring covalently linked flavoenzymes. A judicially functionalized flavin analogue was used for the coupling reaction with the pre-synthesized peptidic motifs using solution-phase chemistry. Representative examples using mono-, di- and tripeptides were reported

  在这里，我们展示了一种简单有效的合成黄素-肽缀合物的合成路线，作为天然存在的共价连接黄素酶的模型。司法功能化的黄素类似物用于使用液相化学与预先合成的肽基序进行偶联反应。据报道，使用单肽、二肽和三肽的代表性例子与黄素部分的 C7 位结合，以展示合成策略的通用性。进一步的光物理研究，包括量子产率测量、浓度依赖性研究和荧光猝灭实验，揭示了在存在酪氨酸的情况下电荷传输过程的分子内性质，类似于在天然对应物中发现的情况。 图形概要 这份手稿讨论了一种简单/有效的合成黄肽缀合物的方法，作为共价类黄素酶的真实模型。设想并进行了适当功能化的黄素部分和预合成的肽实体之间的偶联反应，以证明该方法的普遍性。进一步的光物理研究，包括量子产率测量、浓度依赖性研究和荧光猝灭实验，揭示了在存在酪氨酸的情况下电荷传输过程的分子内性质，类似于在天然对应物中发现的情况。这种合成的黄肽模型可以提供进一步的研究，以深入了解相应的生物学现象。