2-(4-甲氧基苯基氨基)乙酸乙酯 | 50845-77-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(4-甲氧基苯基氨基)乙酸乙酯
• 英文名称: N-(4-methoxy)phenylglycine ethyl ester
• 英文别名: ethyl (4-methoxyphenyl)glycinate；ethyl 2-((4-methoxyphenyl)amino)acetate；ethyl N-(4-methoxyphenyl)glycinate；N-ethoxycarbonylmethyl-4-methoxyaniline；DL-4-methoxyphenylglycine ethyl ester；Ethyl 2-[(4-methoxyphenyl)amino]acetate；ethyl 2-(4-methoxyanilino)acetate
• CAS: 50845-77-7
• 化学式: C₁₁H₁₅NO₃
• mdl: MFCD01972639
• 分子量: 209.245
• InChiKey: TZJRPKDPYLAMJZ-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-[(4-methoxyphenyl)amino]acetate
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: Ethyl 2-[(4-methoxyphenyl)amino]acetate
CAS number: 50845-77-7

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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.

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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.

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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.

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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:

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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.

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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: C11H15NO3
Molecular weight: 209.2

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基氨基)乙酸乙酯 在 eosin 、 copper diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以90%的产率得到Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)-
  参考文献：
  名称：

  曙红-Y/Cu(OAc)2催化甘氨酸酯在黑暗中的有氧氧化偶联反应

  摘要：

  甘氨酸酯与 β-酮酸、吲哚、萘酚和吡咯的催化需氧氧化偶联反应已在环境温度下通过在黑暗中在Cu(OAc) 2存在下操纵 eosin-Y 的基态反应性来实现. 该方法在温和的反应条件下提供结构多样的非天然氨基酸衍生物。进行了紫外-可见吸收光谱法、循环伏安法、X 射线光电子能谱法、高分辨率质谱法和对照实验，以制定合理的机理途径。阶梯经济、广泛的底物范围、使用空气作为绿色氧化剂以及操作简单的设置使该协议对学术和工业应用都具有很高的吸引力。

  DOI：

  10.1039/d2ob00678b
• 作为产物：
  描述：

  Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)- 在 [Ru(CO)2(Ph₄C₄CO)]2 异丙醇 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 以95%的产率得到2-(4-甲氧基苯基氨基)乙酸乙酯
  参考文献：
  名称：

  Efficient ruthenium catalyzed transfer hydrogenation of functionalized imines by isopropanol under controlled microwave heating

  摘要：

  采用异丙醇作为氢源，以[Ru(CO)2(Ph4C4CO)]2 (3)为催化剂，研究了各种官能团化的亚胺的转移氢化反应。在甲苯中使用油浴或控制微波加热，实现了高效的过程，具有高转化频率，并且以高收率获得了产物胺。与传统的[Ru2(CO)4(μ-H)(Ph4C4COHOCC4Ph4)] (1)催化剂相比，催化剂3的一个优点是没有诱导期，这使得与1相比，使用3的反应更快。关键词：转移氢化，钌，亚胺，微波。

  DOI：

  10.1139/v05-103
• 作为试剂：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 异丙基硼酸 在 2-(4-甲氧基苯基氨基)乙酸乙酯 、 氧气 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 以70%的产率得到1-isopropoxy-2,2,6,6-tetramethylpiperidine
  参考文献：
  名称：

  Molecular Oxygen-Mediated Radical Alkylation of C(sp³)–H Bonds with Boronic Acids

  摘要：

  DOI：

  10.1021/acs.orglett.1c00948

文献信息

• Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines
  作者：Renate Rohlmann、Tobias Stopka、Heinrich Richter、Olga Garcı́a Mancheño

  DOI：10.1021/jo4007199

  日期：2013.6.21

  formation or C–C bond formation upon homocondensation or reaction with simple olefins, respectively. Cyclization followed by a final oxidation generates these classes of interesting bioactive heterocycles in one synthetic transformation. Additionally, the one-pot multicomponent synthesis of quinolines from anilines, aldehydes, and olefins has also been successfully developed under these mild oxidative conditions

  已经开发了使用TEMPO氧铵盐作为温和，无毒的氧化剂，由N-烷基苯胺直接催化铁催化的二氢喹唑啉和喹啉的发散性串联氧化反应。Fe（OTf）2是形成二氢喹唑啉的首选路易斯酸催化剂，而FeCl 3则可以更好地合成喹啉。这种发散的方法意味着，对于两种合成，N的α-C（sp 3）–H键的直接氧化功能化-烷基苯胺的出现，分别导致它们与均相缩合或与简单烯烃反应时形成C–N键或形成C–C键。环化后再进行最终氧化，可以在一个合成转化中生成这类有趣的生物活性杂环。此外，在这些温和的氧化条件下，还成功地开发了由苯胺，醛和烯烃单锅多组分合成喹啉的方法。
• Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp³ )−H Alkylation of Glycine and Peptides
  作者：Chao Wang、Mengzhun Guo、Rupeng Qi、Qinyu Shang、Qiang Liu、Shan Wang、Long Zhao、Rui Wang、Zhaoqing Xu

  DOI：10.1002/anie.201809400

  日期：2018.11.26

  well‐developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible‐light‐induced Cu‐catalyzed decarboxylative C(sp3)−H alkylation of glycine for preparing α‐alkylated unnatural α‐amino acids. It merits mentioning that the mild conditions and the good functional‐group tolerance allow the modification

  尽管铜催化方面的工作已经发展成熟并且在不断发展，但是铜作为光催化剂的潜力仍未得到开发。本文报道的是第一个可见光诱导的铜催化甘氨酸脱羧C（sp 3）-H烷基化制备甘氨酸α-烷基化非天然α-氨基酸的例子。值得一提的是，温和的条件和良好的官能团耐受性允许使用此方法对肽进行修饰。机理研究表明，该反应涉及自由基-自由基偶联途径。
• A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions
  作者：Chi-Ming Ho、Jun-Long Zhang、Cong-Ying Zhou、On-Yee Chan、Jessie Jing Yan、Fu-Yi Zhang、Jie-Sheng Huang、Chi-Ming Che

  DOI：10.1021/ja9077254

  日期：2010.2.17

  Water-soluble [Ru(II)(4-Glc-TPP)(CO)] (1, 4-Glc-TPP = meso-tetrakis(4-(beta-D-glucosyl)phenyl)porphyrinato dianion) is an active catalyst for the following carbenoid transfer reactions in aqueous media with good selectivities and up to 100% conversions: intermolecular cyclopropanation of styrenes (up to 76% yield), intramolecular cyclopropanation of an allylic diazoacetate (68% yield), intramolecular

  水溶性 [Ru(II)(4-Glc-TPP)(CO)] (1, 4-Glc-TPP = meso-tetrakis(4-(beta-D-glucosyl)phenyl)porphyrinato dianion) 是一种活性催化剂用于水性介质中的以下类卡宾转移反应，具有良好的选择性和高达 100% 的转化率：苯乙烯的分子间环丙烷化（产率高达 76%）、烯丙基重氮乙酸酯的分子内环丙烷化（产率 68%）、分子内铵/锍叶立德的形成/ [2,3]-sigmatroptic 重排反应（产率高达 91%），以及分子间类卡宾插入芳基伯胺的 NH 键（产率高达 83%）。这种钌糖基化卟啉复合物可以选择性地催化肽的 N 端烷基化（8 个例子），并使用荧光连接的重氮化合物（15）介导蛋白质的 N 端修饰（4 个例子）。荧光基团通过 1 催化烯烃环丙烷化与 15 在水溶液中分两步结合到泛素上：（1）通过 N-羟基琥珀酰亚胺酯
• Copper-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with Imides or Amides for Synthesis of α-Substituted α-Amino Acid Esters
  作者：Zhi-Qiang Zhu、Zong-Bo Xie、Zhang-Gao Le、Li-Jin Xiao、Dong Guo、Yue Lu

  DOI：10.1055/s-0036-1591586

  日期：2018.7

  highly efficient cross-dehydrogenative-­coupling (CDC) reaction between N-aryl glycine esters and imides or amides by the catalysis of a copper salt without the requirement of ­peroxide agents is described. The novel reaction provides a facile ­approach for the synthesis of α-substituted α-amino acid esters through C–H/N–H oxidative cross-coupling. A possible mechanism for the CDC reaction by using copper

  描述了 N-芳基甘氨酸酯与酰亚胺或酰胺之间通过铜盐催化的简单高效的交叉脱氢偶联 (CDC) 反应，无需过氧化物试剂。该新反应为通过 C-H/N-H 氧化交叉偶联合成 α-取代的 α-氨基酸酯提供了一种简便的方法。还提出了使用铜作为催化剂和空气作为末端氧化剂进行CDC反应的可能机制。该合成方法具有收率好、操作简单、反应条件温和等优点。
• 一种3,4-二氢喹唑啉衍生物及其制备方法、应用
  申请人：郑州大学

  公开号：CN110003121A

  公开（公告）日：2019-07-12

  本发明属于有机合成技术领域，具体涉及一种3,4‑二氢喹唑啉衍生物及其制备方法、应用。本发明的3,4‑二氢喹唑啉衍生物，其结构式为其中，R1～R4分别选自氢、卤素、烷基、取代烷基、烷氧基、苄基中的一种；R5～R7分别选自氢、卤素、烷氧基、取代烷基中的一种；R8选自羟基、酰胺基、亚磷酸酯基中的一种。本发明提供了一种多取代的3,4‑二氢喹唑啉衍生物，该3,4‑二氢喹唑啉衍生物具有芳香基，是一种用途广泛的有机合成中间体，在医药生产及有机合成领域具有重要的应用价值，可用作T型钙通道阻滞剂、锥虫硫酮还原酶(TryR)抑制剂和抗癌试剂，并表现出抗肿瘤生物活性。