3-甲基-5-苯基-1,2,4-噁二唑 | 1199-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-甲基-5-苯基-1,2,4-噁二唑
• 中文别名: 3-甲基-5-苯基-1,2,4-恶二唑
• 英文名称: 3-methyl-5-phenyl-[1,2,4]oxadiazole
• 英文别名: 3-Methyl-5-phenyl-[1,2,4]oxadiazol；3-Methyl-5-phenyl-1,2,4-oxdiazol；3-Methyl-5-phenyl-1,2,4-oxadiazole
• CAS: 1199-00-4
• 化学式: C₉H₈N₂O
• mdl: MFCD00464109
• 分子量: 160.175
• InChiKey: ZTWRWSTUMWZTAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Methyl-5-phenyl-1,2,4-oxadiazole
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: 3-Methyl-5-phenyl-1,2,4-oxadiazole
CAS number: 1199-00-4

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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: C9H8N2O
Molecular weight: 160.2

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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：

  3-甲基-5-苯基-1,2,4-噁二唑 生成 1,1,1-trifluoro-3-(5-phenyl-1,2,4-oxadiazol-3-yl)propan-2-one
  参考文献：
  名称：

  SUMIMOTO, SHINZABURO;ISHIZUKA, ICHIRO;KAI, HIROYUKI;UEDA, SHIRO;TAKASE, A+

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenyl-1,2-propanedione dioxime 在 四碘化二磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到3-甲基-5-苯基-1,2,4-噁二唑
  参考文献：
  名称：

  α-二酮肟与四碘化二磷反应制备恶二唑和腈

  摘要：

  摘要 描述了四碘化二磷作为一种新的、温和的缩合剂用于合成恶二唑的用途。这些数据表明肟简单脱水为 1,2,5-恶二唑，以及肟重排为正常贝克曼产物 1,2,4-恶二唑。然而，苯甲醛的单肟经历了异常的贝克曼重排，以苯甲醛为主要产物。所描述的方法对于恶二唑和腈的合成来说既简单又重要。图形概要

  DOI：

  10.1080/00397911.2011.595035

文献信息

• Iron-Catalyzed Highly para-Selective Difluoromethylation of Arenes
  作者：Wei-Tai Fan、Yuting Li、Dongjie Wang、Shun-Jun Ji、Yingsheng Zhao

  DOI：10.1021/jacs.0c09545

  日期：2020.12.9

  bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe(TPP)Cl]-enabled, selective, C-H difluoromethylation of arenes using BrCF2CO2Et as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only

  仅通过改变催化剂体系在间位或对位直接官能化 CH 键是一项重大挑战。我们在此报告了使用 BrCF2CO2Et 作为二氟甲基化源的 [Fe(TPP)Cl] 启用的、选择性的、CH 二氟甲基化芳烃，这成功地改变了从间位到对位的选择性。初步的机理研究表明，铁卟啉配合物不仅激活了芳环，而且由于配体空间的影响，还诱导了对位选择性。
• [EN] NEW INDANYLOXYDIHYDROBENZOFURANYLACETIC ACIDS<br/>[FR] NOUVEAUX ACIDES INDANYLOXYDIHYDROBENZOFURANYLACÉTIQUES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014086712A1

  公开（公告）日：2014-06-12

  The present invention relates to compounds of general formula I, wherein the groups (Het)Ar and R1 are defined as in claim 1, which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及一般式I的化合物，其中基团(Het)Ar和R1的定义如权利要求1中所述，具有有价值的药理特性，特别是与GPR40受体结合并调节其活性。这些化合物适用于治疗和预防可以受到该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。
• Lithiation of five-membered heteroaromatic compounds. The methyl substituted 1,2-azoles, oxadiazoles, and thiadiazoles
  作者：R. G. Micetich

  DOI：10.1139/v70-334

  日期：1970.7.1

  The lithiation of various methyl substituted isoxazoles, isothiazoles, pyrazoles, oxadiazoles, and thiadiazoles using n-butyllithium has been studied. Three types of reactions, namely, lateral lithiation, ring cleavage, and addition of butyllithium to the ring, have been found. 3,5-Dimethylisoxazole, 3-phenyl-5-methylisoxazole, 3,4-dimethyl-1,2,5-oxadiazole, 2,5-dimethyl-1,3,4-thiadiazole, 3-phenyl-5-methyl-1,2,4-oxadiazole, and 3,5-dimethyl-1,2,4-thiadiazole all undergo lateral lithiation to give the respective acetic acids after carboxylation. 1-Methyl-3,5-disubstituted pyrazoles form the 1-lithiomethyl derivatives, while 1-phenyl-3,5-disubstituted pyrazoles are converted to the 1-ortholithiophenyl-3,5-disubstituted pyrazoles. 4-Methylisothiazole is lithiated mainly at C-5, but also suffers ring cleavage to form 1-n-butylthio-2-cyanoprop-1-ene. Heteroaromatic compounds containing an N—S bond, such as 3,4-dimeth yl-1,2,5-thiadiazole, 4-methyl-5-phenyl-1,2,3-thiadiazole, and 3,5-dimethylisothiazole, undergo nucleophilic attack at sulfur with resulting ring cleavage. 3,5-Dimethylisothiazole produces 2-n-butylthiopent-2-en-4-one. 3-Methyl-5-phenyl-1,2,4-oxadiazole gave 3-methyl-5-phenyl-5-n-butyl-1,2,4-dihydroöxadiazole by addition to the azomethine bond. The results of these lithiations are discussed. 3-Methyl-5-lithiomethylisoxazole was converted to various derivatives. Nuclear magnetic resonance spectral analysis was used to establish the identity of the products.

  各种甲基取代异噁唑、异硫唑、吡唑、噁二唑和噻二唑的锂化反应已经被研究。发现了三种类型的反应，即侧链锂化、环裂解和丁基锂加入环中。3,5-二甲基异噁唑、3-苯基-5-甲基异噁唑、3,4-二甲基-1,2,5-噁二唑、2,5-二甲基-1,3,4-噻二唑、3-苯基-5-甲基-1,2,4-噁二唑和3,5-二甲基-1,2,4-噻二唑都经历侧链锂化，在羧化后生成相应的乙酸。1-甲基-3,5-二取代吡唑形成1-锂甲基衍生物，而1-苯基-3,5-二取代吡唑转化为1-邻锂苯基-3,5-二取代吡唑。4-甲基异硫唑主要在C-5处发生锂化，但也发生环裂解形成1-正丁硫基-2-氰基丙-1-烯。含有N—S键的杂环化合物，如3,4-二甲基-1,2,5-噻二唑、4-甲基-5-苯基-1,2,3-噻二唑和3,5-二甲基异硫唑，在硫原子上发生亲核攻击，导致环裂解。3,5-二甲基异硫唑产生2-正丁硫代戊-2-烯-4-酮。3-甲基-5-苯基-1,2,4-噁二唑通过加成到偶氮亚胺键生成3-甲基-5-苯基-5-正丁基-1,2,4-二氢噁二唑。讨论了这些锂化的结果。3-甲基-5-锂甲基异噁唑被转化为各种衍生物。核磁共振光谱分析用于确定产物的身份。
• [EN] PYRIDO (4,3-B) INDOLES CONTAINING RIGID MOIETIES<br/>[FR] PYRIDO[4,3-B]INDOLES CONTENANT DES FRAGMENTS RIGIDES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2010051501A1

  公开（公告）日：2010-05-06

  This disclosure is directed to pyrido[4,3-b]indoles having rigid moieties. The compounds in one embodiment are pyrido[4,3-b]indoles having an unsaturated hydrocarbon moiety. The compounds in another embodiment are pyrido[4,3-b]indoles having a cycloalkyl, cycloalkenyl or heterocyclyl moiety. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及具有刚性基团的吡啶并[4,3-b]吲哚化合物。在一个实施例中，这些化合物是具有不饱和碳氢基团的吡啶并[4,3-b]吲哚化合物。在另一个实施例中，这些化合物是具有环烷基、环烯基或杂环基团的吡啶并[4,3-b]吲哚化合物。还提供了包括这些化合物的药物组合物，以及使用这些化合物在各种治疗应用中的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst
  作者：Anthony R Gangloff、Joane Litvak、Emma J Shelton、David Sperandio、Vivian R Wang、Kenneth D Rice

  DOI：10.1016/s0040-4039(00)02288-7

  日期：2001.2

  Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1–1.0 equivalents of TBAF in THF for 1–24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.

  发现四丁基氟化铵（TBAF）是合成3,5-二取代-1,2,4-恶二唑的温和而有效的催化剂。在室温下，使用THF中的0.1–1.0当量的TBAF，在室温下放置1–24小时，可以将烷酰基-和芳酰氧基am以高收率转化为相应的3,5-二取代-1,2,4-恶二唑。研究了各种R和R'取代基。

表征谱图