2-苯基噁唑-4-羧酸甲酯 | 59171-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基噁唑-4-羧酸甲酯
• 中文别名: 2-苯基恶唑-4-羧酸甲酯
• 英文名称: 2-phenyl-oxazole-4-carboxylic acid methyl ester
• 英文别名: methyl 2-phenyloxazole-4-carboxylate；methyl 2-phenyl-1,3-oxazole-4-carboxylate
• CAS: 59171-72-1
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00522084
• 分子量: 203.197
• InChiKey: JHITWPKHNTXGOB-UHFFFAOYSA-N

物化性质

• 熔点：
  85.5-87 °C
• 沸点：
  327.1±34.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-phenyloxazole-4-carboxylate
Synonyms: 2-Phenyl-oxazole-4-carboxylic acid methyl ester

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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: Methyl 2-phenyloxazole-4-carboxylate
CAS number: 59171-72-1

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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, refrigerated.
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: C11H9NO3
Molecular weight: 203.2

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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-苯基噁唑-4-羧酸甲酯 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到2-苯基-4-噁唑羧酸
  参考文献：
  名称：

  迈向新的三环基序：分子内C–H芳基化是正式[3 + 3]环缩策略的关键步骤

  摘要：

  建立了一种通用的收敛性[3 + 3]环缩合方法，该方法可使用四个异构体[1,3]恶唑并[4,5 - c ] -1-萘啶-4（5 H）-。这种方法的关键合成步骤是：（1）连接两个外围杂环的具有挑战性的酰胺连接基的构建；（2）钯催化的分子内C–H芳基化反应形成关键的杂环。

  DOI：

  10.1002/ejoc.201700020
• 作为产物：
  描述：

  methyl 2-phenyl-2-oxazoline-4-carboxylate 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-苯基噁唑-4-羧酸甲酯
  参考文献：
  名称：

  用DAST和Deoxo-Fluor合成功能化的恶唑啉和恶唑。

  摘要：

  [公式：见正文]使用DAST和Deoxo-Fluor试剂描述了将β-羟基酰胺温和高效环化为恶唑啉的方法。还提出了一种由一锅法从β-羟基酰胺合成恶唑的方案。

  DOI：

  10.1021/ol005777b

文献信息

• Metal-free C–H amination of arene with <i>N</i>-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature
  作者：Qi Miao、Zhong Shao、Cuiying Shi、Lifang Ma、Fang Wang、Ruoqi Fu、Haochen Gao、Ziyuan Li

  DOI：10.1039/c9cc02739d

  日期：——

  amination of arene through C–H bond cleavage employing N-fluorobenzenesulfonimide (NFSI) as the amination reagent in good to excellent yields with broad arene scope in the absence of any metal, ligand or additive is reported. Unlike previous transition metal-catalysed aminations in which high reaction temperatures are usually necessary, this novel reaction at room temperature is the first example of C–H

  据报道，在不使用任何金属，配体或添加剂的情况下，使用N-氟苯磺酰亚胺（NFSI）作为胺化试剂，通过TEMP键催化的芳烃通过C–H键断裂的直接胺化反应具有良好的收率和优异的收率。与以前通常需要高反应温度的过渡金属催化胺化反应不同，这种在室温下的新颖反应是通过有机催化实现的NFSI的C–H胺化反应的第一个例子。还提出了这种简洁胺化的可能机理。
• Chemical Manganese Dioxide (CMD), an Efficient Activated Manganese Dioxide. Application to Oxidation of Benzylic and Allylic Alcohols
  作者：Toyohiko Aoyama、Naoko Sonoda、Mariko Yamauchi、Kyoko Toriyama、Masahiro Anzai、Akira Ando、Takayuki Shioiri

  DOI：10.1055/s-1998-1583

  日期：1998.1

  Oxidation of benzylic and allylic alcohols with chemical manganese dioxide smoothly proceeded under mild reaction conditions to give the corresponding aldehydes and ketones, respectively, in high yields. It is well-known that activated manganese dioxide (MnO2) is a useful reagent both for selective oxidation of benzylic and allylic alcohols to aldehydes and ketones, respectively, and for dehydrogenation

  苯甲醇和烯丙醇与化学二氧化锰的氧化在温和的反应条件下顺利进行，分别以高产率得到相应的醛和酮。众所周知，活化的二氧化锰 (MnO2) 是一种有用的试剂，可分别用于将苯甲醇和烯丙醇选择性氧化成醛和酮，以及将杂环脱氢成杂芳烃。1 虽然已经报道了几种制备活化 的方法，但 2 制备非常繁琐，有时氧化效率缺乏重现性。也可以使用市售的活化MnO 2 ，​​但其活性也有很大差异。我们已经报道了化学二氧化锰 (CMD), 3 用于干电池制造，可有效用于某些烯丙醇 4 的氧化和杂环的脱氢，例如噻唑啉、5 2,3-二氢呋喃、6 3-吡咯啉、7 和 2-吡咯啉。8 沿着这条路线的进一步研究表明，CMD 广泛适用于将苄醇和烯丙醇 1 分别选择性氧化为醛和酮 2，如方案 1 所示。
• Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch−Sosnovsky Reaction
  作者：A. I. Meyers、Francis X. Tavares

  DOI：10.1021/jo9613491

  日期：1996.11.15

  Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative

  使用Kharasch-Sosnovsky反应的改进，将带有各种2-烷基取代基（手性和非手性）的恶唑啉和噻唑啉的氧化分别平滑地氧化为相应的恶唑和噻唑。成功实施此重要氧化反应的关键特征是使用Cu（I）和Cu（II）盐的混合物来增强中间俘虏性自由基的氧化作用24。氧化失败的原因是在C-4处缺少碳烷氧基的恶唑啉/噻唑啉。
• Cobalt-Catalyzed Cross-Dehydrogenative C(sp² )−C(sp³ ) Coupling of Oxazole/Thiazole with Ether or Cycloalkane
  作者：Xiaojiao Wang、Bowen Lei、Lifang Ma、Lisi Zhu、Xinyue Zhang、Hao Zuo、Dailin Zhuang、Ziyuan Li

  DOI：10.1002/asia.201701258

  日期：2017.11.2

  Direct C5‐alkylation of oxazole/thiazole with ether or cycloalkane has been achieved through a cobalt‐catalyzed cross‐dehydrogenative coupling (CDC) process in moderate to good yields. This transformation represents the first C(sp2)−C(sp3) cross‐coupling at the C5‐position of the oxazole/thiazole via double C−H bond cleavages. Various functional groups on oxazole/thiazole substrates, as well as water

  通过钴催化的交叉脱氢偶联（CDC）工艺，恶唑/噻唑与醚或环烷烃直接进行C5-烷基化反应，产率中等至良好。这种转变代表通过双CH键断裂在恶唑/噻唑的C5位上的第一个C（sp 2）-C（sp 3）交叉偶联。简明实用的方案很好地耐受了恶唑/噻唑底物上的各种官能团，以及水和空气，构成了直接进入具有重要医学意义的杂环的方法。还提出了涉及激进过程的初步机制。
• [EN] SUBSTITUTED HYDANTOINAMIDES AS ADAMTS7 ANTAGONISTS<br/>[FR] HYDANTOINAMIDES SUBSTITUÉS EN TANT QU'ANTAGONISTES D'ADAMTS7
  申请人：BAYER AG

  公开号：WO2021094434A1

  公开（公告）日：2021-05-20

  The application relates to substituted hydantoinamides of formula (I) as ADAMTS7 antagonists, to processes for their preparation, their use alone or in combination for the treatment or prophylaxis of diseases, in particular of cardiovascular diseases, including atherosclerosis, coronary artery disease (CAD), peripheral vascular disease (PAD), arterial occlusive disease or restenosis after angioplasty. R1 is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, 5- to 6-membered heteroaryl or phenyl; R2 is hydrogen or alkyl; A is 5-membered heteroaryl; Z is 6- to 10-membered aryl or 5- to 10-membered heteroaryl; all groups being optionally substituted.

  该申请涉及公式（I）的替代咪唑酰脲作为ADAMTS7拮抗剂，以及它们的制备方法，它们单独或与其他药物联合用于治疗或预防疾病，特别是心血管疾病，包括动脉粥样硬化、冠状动脉疾病（CAD）、外周血管疾病（PAD）、动脉闭塞病或血管成形术后再狭窄。R1为氢、烷基、环烷基、杂环烷基、5-至6-成员杂芳基或苯基；R2为氢或烷基；A为5-成员杂芳基；Z为6-至10-成员芳基或5-至10-成员杂芳基；所有基团均可选择性地被取代。