2-(3-甲氧基苯基)-2-甲基丙腈 | 17653-93-9

• 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: 2-(3-甲氧基苯基)-2-甲基丙腈
• 英文名称: 2-(3'-Methoxyphenyl)-2-methylpropionitrile
• 英文别名: 2-(3-methoxyphenyl)-2-methylpropanenitrile；2-(3-methoxy-phenyl)-2-methyl-propionitrile；2-(3-Methoxy-phenyl)-2-methyl-propionitril；2-(3-Methoxyphenyl)-2-methylpropionitrile；m-<2-(2-Cyanopropyl)>-anisol
• CAS: 17653-93-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: YMUMJIHZRRIBPK-UHFFFAOYSA-N

物化性质

• 沸点：
  139.5-144.5 °C(Press: 13.5 Torr)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  存储条件：2-8°C，干燥

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-(3-Methoxyphenyl)-2-methylpropanenitrile
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-(3-Methoxyphenyl)-2-methylpropanenitrile
CAS number: 17653-93-9

---

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: C11H13NO
Molecular weight: 175.2

---

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：

  2-(3-甲氧基苯基)-2-甲基丙腈 在 盐酸 、 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 丙酮 、 二乙二醇 为溶剂， 反应 122.0h， 生成 1,1,4,4-tetramethyl-6-methoxy-3,4-dihydro-1H-2-benzopyran
  参考文献：
  名称：

  Heteroarotinoids Inhibit Head and Neck Cancer Cell Lines in Vitro and in Vivo Through Both RAR and RXR Retinoic Acid Receptors

  摘要：

  A class of less toxic retinoids, called heteroarotinoids, was evaluated for their molecular mechanism of growth inhibition of two head and neck squamous cell carcinoma (HNSCC) cell lines SCC-2 and SCC-38. A series of 14 heteroarotinoids were screened for growth inhibition activity in vitro. The two most active compounds, one that contained an oxygen heteroatom (6) and the other a sulfur heteroatom (16), were evaluated in a xenograph model of tumor establishment in nude mice. Five days after subcutaneous injection of 10(7) SCC-38 cells, groups of 5 nu / nu mice were gavaged daily (5 days/week for 4 weeks) with 20 mg/kg/day of all-trans-retinoic acid (t-RA, 1), 10 mg/kg/day of 6, 10 mg/kg/day of 16, or sesame oil. After a few days, the dose of t-RA (1) was decreased to 10 mg/kg/day to alleviate the side effects of eczema and bone fracture. No significant toxic effects were observed in the heteroarotinoid groups. All three retinoids caused a statistically significant reduction in tumor size as determined by the Student t-test (P < 0.05). Complete tumor regression was noted in 3 of 5 mice treated with t-RA (1), 4 of 5 mice treated with 16, 1 of 5 mice treated with 6, and 1 of 5 mice treated with sesame oil. Reverse transcriptase polymerase chain reaction (RT-PCR) was used to determine that the expression levels of RAR alpha, RXR alpha, and RXR beta were similar in the two cell lines, while RAR beta expression was higher in SCC-2 over SCC-38, and RAR gamma expression was higher in SCC-38 over SCC-2. Receptor cotransfection assays in CV-1 cells demonstrated that 16 was a potent activator of both RAR and RXR receptors, while 6 was selective for the RXR receptors. Transient cotransfection assays in CV-1 cells using an AP-1 responsive reporter plasmid demonstrated that t-RA (1), 6, and 16 each inhibited AP-1-driven transcription in this cell line. In conclusion, the growth inhibition activity of the RXR-selective 6 and the more potent growth inhibition activity of the RAR/RXR pan-agonist 16 implicate both RARs and RXRs in the molecular mechanism of retinoid growth inhibition. Moreover, the chemoprevention activity and the lack of toxicity of heteroarotinoids demonstrate their clinical potential in head and neck cancer chemoprevention.

  DOI：

  10.1021/jm990292i
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 C₇₆H₆₀O₁₀P₂ 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 2-(3-甲氧基苯基)-2-甲基丙腈
  参考文献：
  名称：

  镍催化的α-取代的苯乙烯的Markovnikov氢氰化反应合成叔苄腈。

  摘要：

  α-取代的苯乙烯的马尔科夫尼科夫氢氰化能够在镍催化下合成叔苄腈。无路易斯酸的转化具有前所未有的官能团耐受性，包括-OH和-NH2基团。以良好至优异的产率获得了广泛的叔苄腈。另外，初步研究了该反应的不对称形式。

  DOI：

  10.1021/acs.orglett.9b04554

文献信息

• Palladium-Catalyzed Distal <i>m</i>-C–H Functionalization of Arylacetic Acid Derivatives
  作者：Dasari Srinivas、Gedu Satyanarayana

  DOI：10.1021/acs.orglett.1c02460

  日期：2021.10.1

  Herein, we present m-C–H olefination on derivatives of phenylacetic acids by tethering with a simple nitrile-based template through palladium catalysis. Notably, the versatility of the method is evaluated with a wide range of phenylacetic acid derivatives for obtaining the meta-olefination products in fair to excellent yields with outstanding selectivities under mild conditions. Significantly, the

  在此，我们通过钯催化与简单的腈基模板连接，在苯乙酸衍生物上进行m -C-H 烯化。值得注意的是，该方法的多功能性是用范围广泛的苯乙酸衍生物来评估的，以便在温和的条件下以中等至极好的收率和出色的选择性获得间烯烃化产物。重要的是，本策略成功地用于合成药物/天然产物类似物（萘普生、布洛芬、扑热息痛和胆固醇）。
• [DE] TETRAHYDRONAPHTHALINDERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ENTZÜNDUNGSHEMMER<br/>[EN] 1-AMINO-2-OXY-SUBSTITUTED TETRAHYDRONAPHTALENE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, AND THEIR USE AS ANTIPHLOGISTICS<br/>[FR] DERIVES DE TETRAHYDRONAPHTALENE A SUBSTITUTION 1-AMINO-2-OXY, PROCEDES POUR LEUR PRODUCTION ET LEUR UTILISATION EN TANT QU'ANTI-INFLAMMATOIRES
  申请人：SCHERING AG

  公开号：WO2005034939A1

  公开（公告）日：2005-04-21

  Die Erfindung betrifft mehrfach substituierte Tetrahydronaphthalinderivate der Formel (I), Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer.

  这项发明涉及公式（I）的多取代四氢萘衍生物，其制备方法以及它们作为抗炎药物的用途。
• [EN] CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] DERIVES DE CHROMENE A TITRE D'AGENTS ANTI-INFLAMMATOIRES
  申请人：PHARMACIA CORP

  公开号：WO2004087687A1

  公开（公告）日：2004-10-14

  The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.

  该发明涉及在治疗与环氧合酶-2介导的疾病相关的情况中具有效用的方法和化合物。特别感兴趣的化合物是由式(I)定义的苯并吡喃和它们的类似物。其中Z、X、R1、R2、R3和R4如规范中所述。
• Design, Synthesis, and <i>in Vitro</i> Evaluation of Cyclic Nitrones as Free Radical Traps for the Treatment of Stroke
  作者：Thomas L. Fevig、S. Marc Bowen、David A. Janowick、Bryan K. Jones、H. Randall Munson、David F. Ohlweiler、Craig E. Thomas

  DOI：10.1021/jm960243v

  日期：1996.1.1

  Analogs of the cyclic nitrone free radical trap 1 (3,3-dimethyl-3,4-dihydroisoquinoline N-oxide, a cyclic analog of phenyl-tert-butylnitrone (PBN)) were prepared in which (1) the fused phenyl ring was replaced with a naphthalene ring, an electron rich heterocycle, or a dimethylphenol, (2) the nitrone-containing ring comprised five, six, or seven atoms, and (3) the gem-dimethyl group was replaced with

  制备环状硝酮自由基阱1的类似物（3,3-二甲基-3,4-二氢异喹啉N-氧化物，苯基叔丁基硝酮（PBN）的环状类似物），其中（1）为稠合的苯环（2）含氮原子的环包含五个，六个或七个原子，并且（3）宝石二甲基被螺环基团取代；最具活性的抗氧化剂，带有与7元环硝酮（化合物6h）融合的二甲基苯酚，在体外抑制脂质过氧化，IC5​​0为22 microM，比1的IC50改善75倍。先前观察到的亲脂性之间的相关性这项研究进一步证实和完善了活性与脂质过氧化的关系。此外，某些类别的化合物（即，
• Novel, potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors as potential therapeutics for osteoporosis with dual human and mouse activities
  作者：Enrico Perspicace、Liliana Cozzoli、Emanuele M. Gargano、Nina Hanke、Angelo Carotti、Rolf W. Hartmann、Sandrine Marchais-Oberwinkler

  DOI：10.1016/j.ejmech.2014.06.036

  日期：2014.8

  osteoporosis. Herein, we describe the design, the synthesis and the biological evaluation of 24 new 17β-HSD2 inhibitors in the 5-substituted thiophene-2-carboxamide class. Structure–activity and structure–selectivity relationships have been explored by variation of the sulfur atom position in the central core, exchange of the thiophene by a thiazole, substitution of the amide group with a larger moiety, exchange

  17β羟基类固醇脱氢酶2型（17β-HSD2）负责将高活性的雌二醇（E2）和睾酮（T）的氧化到更弱的雌酮（E1）和Δ 4雄甾烯-3,17-二酮（Δ 4-AD）。由于17β-HSD2存在于骨骼中，并且由于雌二醇和睾丸激素能够诱导骨骼形成并抑制骨骼吸收，因此抑制这种酶可能是治疗骨质疏松症的一种新的有希望的方法。在本文中，我们描述了24种新型的5取代噻吩-2-羧酰胺类17β-HSD2抑制剂的设计，合成和生物学评估。通过改变中心核中硫原子的位置，噻唑被噻唑交换，酰胺基被较大部分取代，N-甲基酰胺基与生物等排物交换，探索了结构-活性和结构-选择性之间的关系。像N-甲基磺酰胺-甲基硫代酰胺和酮，以及噻吩核心的2和3位被烷基和苯基取代，从而生成2,3,5-三取代的噻吩衍生物。在人和小鼠的酶上评估了这些化合物。从这项研究中，鉴定出一种在人和小鼠17β-HSD2酶中均有效的新型选择性化合物，化合物21（IC