1-[2-硝基-4-(三氟甲基)苯基]哌啶 | 1692-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-[2-硝基-4-(三氟甲基)苯基]哌啶
• 英文名称: 1-(2-nitro-4-(trifluoromethyl)phenyl)piperidine
• 英文别名: 1-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine
• CAS: 1692-79-1
• 化学式: C₁₂H₁₃F₃N₂O₂
• 分子量: 274.243
• InChiKey: ZKCJWUWQXSPDEO-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50°C
• 沸点：
  342.8±42.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38

SDS

Name:	1-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine 97% Material Safety Data Sheet
Synonym:
CAS:	1692-79-1

Section 1 - Chemical Product MSDS Name:1-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1692-79-1	1-[2-Nitro-4-(trifluoromethyl)phenyl]p	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1692-79-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 48 - 50 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H13F3N2O2
Molecular Weight: 274

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1692-79-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 1692-79-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1692-79-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1692-79-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-[2-硝基-4-(三氟甲基)苯基]哌啶 在 盐酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 N-(2-(哌啶-1-基)-5-(三氟甲基)苯基)异烟酰胺
  参考文献：
  名称：

  具有抗白血病作用和对富含丝氨酸/精氨酸的蛋白激酶（SRPK）具有细胞内抑制活性的三氟甲基芳基酰胺。

  摘要：

  在许多癌症中，经常发现富含丝氨酸/精氨酸的蛋白激酶（SRPK）的活性发生了变化，这表明它们可以作为肿瘤学中潜在的治疗靶标。在这里，我们描述了基于已知的SRPKs抑制剂N-（2-（2-哌啶-1-基）-5-（三氟甲基）苯基）异烟酰胺（SRPIN340）的一系列22种三氟甲基芳基酰胺的合成及其抗白血病的评估效果。与SRPIN340相比，某些衍生物对髓样和淋巴白血病细胞系表现出优异的细胞毒性作用。特别是，化合物24、30和36的IC50值介于6.0和35.7μM之间。另外，这三种化合物能够触发细胞凋亡和自噬，并表现出与化学治疗剂长春新碱的协同作用。此外，化合物30在削弱SR蛋白的细胞内磷酸化状态以及MAP2K1，MAP2K2，VEGF和RON致癌同工型的表达方面比SRPIN340更有效。因此，获得了具有增强的针对SRPK活性的细胞内作用的新型化合物，有助于药物化学努力开发新的抗癌剂。

  DOI：

  10.1016/j.ejmech.2017.03.078
• 作为产物：
  描述：

  4-氯-3-硝基三氟甲苯 在 /BRN= 102438/ 作用下， 以 苯 为溶剂， 生成 1-[2-硝基-4-(三氟甲基)苯基]哌啶
  参考文献：
  名称：

  在苯中被哌啶或[ 1-2 H]哌啶活化的芳族取代基。动力学氘同位素效应对位移组的依赖性

  摘要：

  1-氯-4,7-二硝基萘（A），4-氯-3-硝基三氟甲苯（B，B'），2,4-二硝基苯基环己基醚（C），1-氟-4-硝基苯（ D）或1-氟-4,7-二硝基萘（E）与哌啶或[ 1-2 H]哌啶仅形成N -4,7-二硝基萘-（A，E），N -2-nitro-4 -三氟甲基苯基-（B，B'），N -2,4-二硝基苯基-（C）或N已经测量了-4-硝基苯基-哌啶（D）作为苯中亲核试剂浓度的函数。哌啶加速速率的程度和动力学氘同位素效应的值都随离去基团而变化。当离去基团是氯时，与先前的报道相反，发现哌啶仅以线性方式非常缓慢地促进了反应。此外，用氘代胺（90％氘代）代替哌啶不会明显改变动力学。当为环己氧基-（C）或氟化物（D，E）时，获得三级动力学（胺浓度为二级）。轻胺在氘代化合物上的相对反应性对于反应C为1·49±0·03，对于反应E为1·03±0·04，并且ca。对于反应D，为1·1。这些事实在中间体

  DOI：

  10.1039/j29680001595

文献信息

• Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC
  作者：Niginia Borlinghaus、Tharique N. Ansari、Leon H. von Garrel、Deborah Ogulu、Sachin Handa、Valentin Wittmann、Wilfried M. Braje

  DOI：10.1039/d1gc00128k

  日期：——

  nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability

  使用廉价的，良性的，和可持续的聚合物，在水中的羟丙基甲基纤维素（HPMC）使亲核芳族subsitution（S Ñ各种亲核和亲电子之间的Ar）的反应。温和的反应条件促进了宽泛的官能团耐受性，该耐受性可用于随后的衍生化以合成药学上相关的结构单元。仅等摩尔量的所有试剂和水作为反应溶剂的使用揭示了本文提出的方法的绿色和可持续性。
• Discovery of Selective Inhibitors of Endoplasmic Reticulum Aminopeptidase 1
  作者：Zachary Maben、Richa Arya、Digamber Rane、W. Frank An、Shailesh Metkar、Marc Hickey、Samantha Bender、Akbar Ali、Tina T. Nguyen、Irini Evnouchidou、Roger Schilling、Efstratios Stratikos、Jennifer Golden、Lawrence J. Stern

  DOI：10.1021/acs.jmedchem.9b00293

  日期：2020.1.9

  clohexyl)-3-(p-tolyl)urea) are competitive inhibitors of ERAP1 aminopeptidase activity. Compound 3 (4-methoxy-3-(N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)sulfamoyl)benzoic acid) allosterically activates ERAP1's hydrolysis of fluorogenic and chromogenic amino acid substrates but competitively inhibits its activity toward a nonamer peptide representative of physiological substrates. Compounds

  ERAP1是一种内质网驻留的锌氨基肽酶，通过修剪肽以加载到主要的组织相容性复合蛋白上，在免疫系统中起着重要的作用。在这里，我们报道了对它的旁系同源物ERAP2和IRAP有选择性的ERAP1抑制剂的发现。化合物1（N-（N-（2-（1H-吲哚-3-基）乙基）氨基甲酰胺基）-2,5-二氟苯磺酰胺）和化合物2（1-（1-（1-（4-乙酰基哌嗪-1-羰基）环己基）-3-（对甲苯基）脲）是ERAP1氨肽酶活性的竞争性抑制剂。化合物3（4-甲氧基-3-（N-（2-（哌啶-1-基）-5-（三氟甲基）苯基）氨磺酰基）苯甲酸）变构活化ERAP1水解有荧光和发色氨基酸底物的水解作用，但竞争性地抑制了它的水解对代表生理底物的九聚体肽的活性。化合物2和3在细胞测定中抑制抗原呈递。化合物3显示出与自身免疫性疾病风险增加相关的ERAP1变体更高的效力。这些抑制剂为确定ERAP1，ERAP2和IRAP特异性的决定因素提
• Optimisation of 2-(N-phenyl carboxamide) triazolopyrimidine antimalarials with moderate to slow acting erythrocytic stage activity
  作者：Brodie L. Bailey、William Nguyen、Anna Ngo、Christopher D. Goodman、Maria R. Gancheva、Paola Favuzza、Laura M. Sanz、Francisco-Javier Gamo、Kym N. Lowes、Geoffrey I. McFadden、Danny W. Wilson、Benoît Laleu、Stephen Brand、Paul F. Jackson、Alan F. Cowman、Brad E. Sleebs

  DOI：10.1016/j.bioorg.2021.105244

  日期：2021.10

  the Janssen Jumpstarter library against the asexual stages of the P. falciparum parasite. Here we describe the structure activity relationship of the identified class and the optimisation of asexual stage activity while maintaining selectivity against the human HepG2 cell line. The most potent analogues from this study were shown to exhibit equipotent activity against P. falciparum multidrug resistant

  疟疾是由从该属的寄生虫毁灭性的寄生虫病疟原虫。据报道，所有临床上可用的抗疟药都存在治疗耐药性，威胁到我们控制疾病的能力，因此持续需要开发新型抗疟药。为了实现这一目标，我们从 Janssen Jumpstarter 库的高通量筛选中针对恶性疟原虫的无性阶段鉴定了 2-（N-苯基甲酰胺）三唑并嘧啶类寄生虫。在这里，我们描述了已识别类别的结构活性关系和无性阶段活性的优化，同时保持对人 HepG2 细胞系的选择性。本研究中最有效的类似物显示出对恶性疟原虫多药耐药菌株和诺氏疟原虫无性寄生虫的等效活性。无性阶段表型研究确定三唑并嘧啶类在滋养体阶段捕获寄生虫，但这些寄生虫很可能在第二个无性周期之前仍然具有代谢活性，因此具有中度至缓慢的作用开始。在体外观察到中心羧酰胺的非 NADPH 依赖性降解和低水溶性ADME 分析。一个重大挑战仍然是纠正这些缺陷，以进一步推进 2-( N-苯基甲酰胺) 三唑并嘧啶支架
• A cavitand stabilizes the Meisenheimer complex of SNAr reactions
  作者：Sara M. Butterfield、Julius Rebek Jr.

  DOI：10.1039/b700319f

  日期：——

  A deep cavitand binds amine nucleophiles and accelerates their subsequent SNAr reactions by solvating the intermediate Meisenheimer complex.

  一个深层的空腔化合物结合胺类亲核试剂，并通过溶剂化中间体梅森海默复合物加速其后续的SNAr反应。
• The Effects of Ring Substituents and Leaving Groups on the Kinetics of SNAr Reactions of 1-Halogeno- and 1-Phenoxy-nitrobenzenes with Aliphatic Amines in Acetonitrile
  作者：Michael R. Crampton、Thomas A. Emokpae、Chukwuemeka Isanbor

  DOI：10.1002/ejoc.200600968

  日期：2007.3

  attack although this may be mediated by reduced steric congestion around the reaction centre. Specific steric effects, leading to rate-retardation, is noted for the ortho-CF3 group. The 1-phenoxy compounds are subject to base catalysis and values of kAm/k–1 are reduced relative to more strongly activated compounds. This is likely to reflect increases in values of k–1 coupled with decreases in values of

  报告了一系列 1-氯-、1-氟-和 1-苯氧基-硝基苯的反应速率常数，这些苯由 CF3 或 CN 基团或环氮与正丁胺、吡咯烷或哌啶在乙腈中活化。将结果与先前报告的更强环活化化合物的结果进行比较。环活化的减少导致亲核攻击的 k1 值降低，尽管这可能是通过减少反应中心周围的空间拥挤来介导的。注意到邻位 CF3 组的特定空间效应导致速率延迟。1-苯氧基化合物受碱催化作用，相对于活性更强的化合物，kAm/k–1 值降低。这可能反映了 k-1 值的增加以及 kAm 值的降低，因为从两性离子中间体到催化胺的质子转移在热力学上变得不太有利。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)