4-(甲氧基羰基)-2-硝基苯乙酸甲酯 | 334952-07-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 4-(甲氧基羰基)-2-硝基苯乙酸甲酯
• 中文别名: 2-(4-甲氧基羰基-2-硝基苯基)乙酸甲酯；4-(2-甲氧基-2-氧代乙基)-3-硝基苯甲酸甲酯
• 英文名称: methyl 2-[4-(methyloxycarbonyl)-2-nitrophenyl]-acetate
• 英文别名: 4-methoxycarbonylmethyl-3-nitrobenzoic acid methyl ester；methyl 4-(methyl acetate-2-yl)-3-nitrobenzoate；(4-methoxycarbonyl-2-nitro-phenyl)-acetic acid methyl ester；(4-Methoxycarbonyl-2-nitro-phenyl)-essigsaeure-methylester；methyl 4-methoxycarbonylmethyl-3-nitro-benzoate；Methyl 4-(2-methoxy-2-oxoethyl)-3-nitrobenzoate
• CAS: 334952-07-7
• 化学式: C₁₁H₁₁NO₆
• 分子量: 253.211
• InChiKey: DCDSLKRPXTVJSA-UHFFFAOYSA-N

物化性质

• 熔点：
  77℃
• 沸点：
  370℃
• 密度：
  1.318
• 闪点：
  163℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8°C，密封，干燥。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 2-(4-methoxycarbonyl-2-nitrophenyl)acetate
Synonyms: Methyl 4-(2-methoxy-2-oxoethyl)-3-nitrobenzoate

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2-(4-methoxycarbonyl-2-nitrophenyl)acetate
CAS number: 334952-07-7

---

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: C11H11NO6
Molecular weight: 253.2

---

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：

  4-(甲氧基羰基)-2-硝基苯乙酸甲酯 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~110.0 ℃ 、344.75 kPa 条件下， 反应 5.5h， 生成 尼达尼布
  参考文献：
  名称：

  OXINDOLE INHIBITORS OF TYROSINE KINASE

  摘要：

  本发明涉及新的酪氨酸激酶的氧吲哚抑制剂，其药物组成物以及使用方法。

  公开号：

  US20150284327A1
• 作为产物：
  描述：

  间硝基苯甲酸 在 硫酸 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(甲氧基羰基)-2-硝基苯乙酸甲酯
  参考文献：
  名称：

  用于改善药代动力学特性的氘代尼达尼布的设计、合成和生物学评价

  摘要：

  尼达尼布是一种新型三联血管激酶抑制剂，可同时抑制三种生长因子。在体外和体内制备和评估了某些代谢活性位点的尼达尼布氘代衍生物。特别是，与尼达尼布相比，氘代化合物 SKLB-C2202 具有显着改善的药代动力学特性。这些努力为进一步研究 SKLB-C2202 的成药性奠定了基础。

  DOI：

  10.1002/jlcr.3299

文献信息

• Substituted indolines which inhibit receptor tyrosine kinases
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US06762180B1

  公开（公告）日：2004-07-13

  Indolinones of the formula having an inhibitory effect on receptor tyrosine kinases and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumor cells. Exemplary are: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone, and (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-metboxycarbonyl-2-indolinone.

  公式为的吲哚酮对受体酪氨酸激酶和细胞周期蛋白/CDK复合物，以及内皮细胞和各种肿瘤细胞的增殖具有抑制作用。示例包括： (a) 3-Z-[1-(4-(哌啶-1-基甲基)-苯胺基)-1-苯基亚甲基]-6-乙氧羰基-2-吲哚酮， (b) 3-Z-(1-(4-(哌啶-1-基甲基)-苯胺基)-1-苯基亚甲基)-6-氨基甲酰基-2-吲哚酮，以及 (c) 3-Z-[1-(4-(哌啶-1-基甲基)-苯胺基)-1-苯基亚甲基]-6-甲氧羰基-2-吲哚酮。
• [EN] PROCESS FOR THE MANUFACTURE OF AN INDOLINONE DERIVATIVE<br/>[FR] PROCÉDÉ DE FABRICATION D'UN DÉRIVÉ D'INDOLINONE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009071523A1

  公开（公告）日：2009-06-11

  The present invention relates to a process for the manufacture of a specific indolinone derivative and a pharmaceutically acceptable salt thereof, namely 3-Z-[1-(4-(N-((4-methyl-piperazin-1-yl)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone and its monoethanesulfonate, to new manufacturing steps and to new intermediates of this process.

  本发明涉及一种制备特定吲哚酮衍生物及其药用可接受盐的方法，即3-Z-[1-(4-(N-((4-甲基哌嗪-1-基)-甲酰基)-N-甲基氨基)-苯胺基)-1-苯基亚甲基]-6-甲氧羰基-2-吲哚酮及其单乙磺酸盐，以及该方法的新制造步骤和新中间体。
• Synthesis and Photophysical Characterization of a New, Highly Hydrophilic Caging Group
  作者：Klaus Schaper、S. Abdollah Madani Mobarekeh、Christof Grewer

  DOI：10.1002/1099-0690(200203)2002:6<1037::aid-ejoc1037>3.0.co;2-4

  日期：2002.3

  system), their photochemical properties (quantum yield and kinetics of the photorelease), and their physical properties (high hydrophilicity) are not satisfactory. In order to address the last problem, we examined means to increase the hydrophilicity of caged compounds based on the o-nitrobenzyl moiety. Here, we report the synthesis and the photochemical and biological characterization of a new caged D-aspartate

  邻硝基苄基保护的生物活性化合物是生物物理学中的有用工具，允许以高时间和空间精度控制生物活性化合物的光释放。因此，可以比以前更详细地研究生物过程，例如神经递质-受体相互作用和许多其他过程。在这方面，这些笼状化合物已成为非常有用的工具。然而，在某些情况下，它们的生物特性（笼状化合物不应与生物系统相互作用）、它们的光化学特性（光释放的量子产率和动力学）和它们的物理特性（高亲水性）并不令人满意。为了解决最后一个问题，我们研究了增加基于邻硝基苄基部分的笼状化合物亲水性的方法。这里，我们报告了一种新的笼状 D-天冬氨酸衍生物的合成以及光化学和生物表征，与之前报道的衍生物相比，该衍生物具有极大的改善的亲水性，并且具有令人满意的光物理特性。因此，具有这种改进的邻硝基苄基的笼状化合物可能代表了用于不同类型生物物理研究的有价值的新工具。(© Wiley-VCH Verlag GmbH, 69451 Weinheim
• Room-Temperature, Ligand- and Base-Free Heck Reactions of Aryl Diazonium Salts at Low Palladium Loading: Sustainable Preparation of Substituted Stilbene Derivatives
  作者：François-Xavier Felpin、Karinne Miqueu、Jean-Marc Sotiropoulos、Eric Fouquet、Oier Ibarguren、Julia Laudien

  DOI：10.1002/chem.200903050

  日期：——

  excellent stereoselectivity. The environmentally friendly protocol developed in this work features low palladium loading in technical‐grade methanol at room temperature under base‐, additive‐, and ligand‐free conditions. The same protocol applied to simple Heck coupling of aryl diazonium salts with methyl acrylate allows astonishingly low palladium loading, down to 0.005 mol %. The stereoselectivity experimentally

  芳基重氮盐与2-芳基丙烯酸酯的Pd（OAc）2催化的Heck反应导致顺式-苯乙烯基苯甲酸酯具有良好的至优异的立体选择性。这项工作开发的环保协议的特点是，在室温下，在无碱，无添加剂和无配体的条件下，钯在工业级甲醇中的负载量较低。应用于芳基重氮盐与丙烯酸甲酯的简单Heck偶联的相同方案可实现低至0.005 mol％的低钯负载量。通过DFT计算合理化了实验观察到的合成顺式-苯乙烯衍生物的立体选择性。此外，通过计算研究已经清楚了甲醇在促进反应中的作用。
• 吲哚酮衍生物及其制药用途
  申请人：成都大学

  公开号：CN112574094B

  公开（公告）日：2022-07-01

  本发明提供了一种吲哚酮衍生物及其制药用途。该吲哚酮衍生物的结构如式(A)所示。实验结果表明，本发明提供的化合物具有比BIBF1120明显提高的药代动力学性质，同时对VEGFR、FGFR和PDGFR均具有优异的抑制效果，可以作为VEGFR、FGFR和/或PDGFR抑制剂，作为血管生成抑制剂，作为预防和/或治疗包括咽鳞癌在内的多种肿瘤的药物，具有广阔的应用前景。