2-氯-1-(4-苯基哌唑)乙酮 | 14761-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-氯-1-(4-苯基哌唑)乙酮
• 中文别名: 2-氯-1-(4-苯基哌嗪)-1-乙酮
• 英文名称: 1-(chloroacetyl)-4-phenylpiperazine
• 英文别名: 2-chloro-1-(4-phenylpiperazin-1-yl)ethan-1-one；2-chloro-1-(4-phenylpiperazin-1-yl)ethanone；4-phenyl-1-chloroacetyl piperazine
• CAS: 14761-39-8
• 化学式: C₁₂H₁₅ClN₂O
• mdl: MFCD00495576
• 分子量: 238.717
• InChiKey: VHIWWIFXKVGUMK-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73°C
• 沸点：
  404.7±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R20/21/22,R34
• 海关编码：
  2933599090

SDS

Name:	2-Chloro-1-(4-phenylpiperazino)ethan-1-one tech Material Safety Data Sheet
Synonym:
CAS:	14761-39-8

Section 1 - Chemical Product MSDS Name:2-Chloro-1-(4-phenylpiperazino)ethan-1-one tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14761-39-8	2-Chloro-1-(4-phenylpiperazino)ethan-1		unlisted

Hazard Symbols: C
Risk Phrases: 20/21/22 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed. Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Harmful if absorbed through the skin. Causes skin burns.
Ingestion:
Harmful if swallowed. Causes gastrointestinal tract burns.
Inhalation:
Harmful if inhaled. Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 14761-39-8: 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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 77 - 79 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: C12H15ClN2O
Molecular Weight: 238.72

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14761-39-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-1-(4-phenylpiperazino)ethan-1-one - 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
Shipping Name: CORROSIVE SOLID, TOXIC, N.O.S.*
Hazard Class: 8 (6.1)
UN Number: 2923
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, TOXIC, N.O.S.
Hazard Class: 8 (6.1)
UN Number: 2923
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, TOXIC, N.O.S.
Hazard Class: 8
UN Number: 2923
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 14761-39-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14761-39-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14761-39-8 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：

  2-氯-1-(4-苯基哌唑)乙酮 在 sodium azide 、 sodium iodide 作用下， 以 水 、 丙酮 为溶剂， 生成 2-azido-1-(4-phenylpiperazin-1-yl)ethanone
  参考文献：
  名称：

  松萝酸烯胺酮偶联的1,2,3-三唑类用作抗菌剂和抗结核剂。

  摘要：

  （+）-尿酸是地衣中的二次代谢产物，具有广泛的生物学特性，例如抗肿瘤，抗微生物，抗病毒，抗炎和杀虫活性。对这些药理活性感兴趣并挖掘其潜力，我们在此介绍新的松萝酸烯胺酮偶联的1,2,3-三唑10-44作为抗分枝杆菌药的合成和生物学评估。将（+）-松香酸与炔丙基胺缩合，得到具有末端乙炔基部分的松香酸烯胺酮8。在铜催化下，它进一步与各种叠氮化物A1-A35反应，以高收率得到三唑10-44。在合成的化合物中，糖精衍生物36被证明是活性最高的类似物，在MIC值为2.5μM时可抑制结核分枝杆菌（Mtb）。类似物16和27，以及3，4-二氟苯酰基和2-酰基萘单元分别在MIC值为5.4和5.3μM时抑制Mtb。在测试的革兰氏阳性和革兰氏阴性细菌中，新衍生物对枯草芽孢杆菌具有活性，化合物18 [3-（三氟甲基）苯甲酰基]和29（N-酰基吗啉基）分别显示抑制浓度41和90.7μM，而它们对其他测试细菌菌株没有

  DOI：

  10.1021/acs.jnatprod.9b00475
• 作为产物：
  描述：

  N-苯基哌嗪 、 氯乙酰氯 以 乙醚 为溶剂， 反应 24.0h， 生成 2-氯-1-(4-苯基哌唑)乙酮
  参考文献：
  名称：

  新型 5-取代 1,2,4-TRIAZOLE-3-Thione 衍生物的合成

  摘要：

  摘要 在本文中，我们描述了 1,2,4-三唑-3-硫醇系列新衍生物的制备。使用3-酰基二硫代氨基甲酸甲酯作为原料，其与胺反应得到相应的4,5-二取代的1,2,4-三唑-3-硫醇衍生物(3)。将β-羟乙基取代基引入1,2,4-三唑-3-硫醇系统的4-位（化合物4）。这些化合物用碘甲烷烷基化为 6，用氯乙酸的 N-取代酰胺（产物 7 和 8），氨基甲基化，形成曼尼希碱 (10)，一些硫醇 4 被脱硫为 9。新化合物对它们的循环活性进行了测试，但发现没有药理活性。

  DOI：

  10.1080/10426500008045234

文献信息

• Substituted uracil derivatives as potent inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1)
  作者：Henning Steinhagen、Michael Gerisch、Joachim Mittendorf、Karl-Heinz Schlemmer、Barbara Albrecht

  DOI：10.1016/s0960-894x(02)00602-9

  日期：2002.11

  A new class of PARP-1 inhibitors, namely substituted fused uracil derivatives were synthesised. Starting from a derivative with an IC(50)=2microM the chemical optimisation program led to compounds with more than a 100-fold increase in potency (IC(50)<20nM). Additionally, physicochemical and pharmacokinetic properties were evaluated. It could be shown that compounds bearing a piperazine or phenyl substituted

  合成了一类新的PARP-1抑制剂，即取代的稠合尿嘧啶衍生物。从IC（50）= 2microM的衍生物开始，化学优化程序导致化合物的效力增加了100倍以上（IC（50）<20nM）。另外，评估了理化和药代动力学性质。可以证明带有哌嗪或苯基取代的βAla-Gly侧链的化合物表现出最佳的整体性能。
• Indoles and 1-(3-(benzyloxy)benzyl)piperazines: Reversible and selective monoamine oxidase B inhibitors identified by screening an in-house compound library
  作者：Damijan Knez、Martina Hrast、Rok Frlan、Anja Pišlar、Simon Žakelj、Janko Kos、Stanislav Gobec

  DOI：10.1016/j.bioorg.2021.105581

  日期：2022.2

  perazine (16 analogues) MAO-B inhibitors were derived from hits, and screened for their structure-activity relationships. Both series yielded low micromolar selective inhibitors of human MAO-B, namely indole 2 (IC50 = 12.63 ± 1.21 µM) and piperazine 39 (IC50 = 19.25 ± 4.89 µM), which is comparable to selective MAO-B inhibitor isatin (IC50 = 6.10 ± 2.81 µM), yet less potent in comparison to safinamide

  单胺氧化酶 A 和 B（MAO-A 和 MAO-B）抑制剂的治疗适应症来自对神经和肿瘤疾病的动物和细胞模型的生物学研究，已将药物发现项目集中在识别可逆的 MAO 抑制剂上。对我们内部学术化合物库的筛选确定了两种抑制 MAO-B 的热门化合物，IC 50值在微摩尔范围内。两个系列的吲哚（23 个类似物）和 3-（苄氧基）苄基）哌嗪（16 个类似物）MAO-B 抑制剂来源于命中，并筛选了它们的构效关系。这两个系列均产生了低微摩尔选择性人 MAO-B 抑制剂，即吲哚2 (IC 50 = 12.63 ± 1.21 µM) 和哌嗪39 (IC 50 = 19.25 ± 4.89 µM)，与选择性 MAO-B 抑制剂 isatin (IC 50 = 6.10 ± 2.81 µM) 相当，但与 safinamide (IC 50 = 0.029 ± 0.002 µM)相比效力较低。选择性 MAO-B 抑
• Synthesis of Triazole-Linked Glycoconjugates by Copper(I)-Catalyzed Regiospecific Cycloaddition of Alkynes and Azides
  作者：Xiaoru Zhang、Xiaohui Yang、Shusheng Zhang

  DOI：10.1080/00397910802431198

  日期：2009.2.9

  Abstract Several 1,2,3-triazole-linked glycoconjugates were efficiently synthesized via a Cu(I)-mediated 1,3-dipolar cycloaddition with high regiospecificity and yield (≥ 85%), providing a simple and efficient route to synthesize protected and unprotected neoglycoconjugates. Introduction of a spacer between glycosyl moieties and other compounds reduces steric hindrance, promotes yield, and expands

  摘要 通过 Cu(I) 介导的 1,3-偶极环加成反应高效合成了几种 1,2,3-三唑连接的糖缀合物，具有高区域特异性和产率（≥ 85%），为合成受保护和未受保护的新糖缀合物。在糖基部分和其他化合物之间引入间隔基可减少空间位阻，提高产量，并扩大糖缀合物的种类以满足生物事件的各种需要。所有合成的糖缀合物的结构均通过红外 (IR)、1H NMR、13C NMR、元素分析 (EA) 或 MS 明确证实。
• Design, Synthesis <i>In Vitro</i> Anticancer Activity and Docking Studies of (−)‐Catechin Derivatives
  作者：Deepak Kumar、S. J. Harshavardhan、Sridhar Chirumarry、Y. Poornachandra、Kiwan Jang、C. Ganesh Kumar、Yong‐Jin Yoon、Bao‐Xiang Zhao、Jun‐Ying Miao、Dong‐Soo Shin

  DOI：10.1002/bkcs.10108

  日期：2015.2

  cytotoxicity against four selected human cancer cell lines by standard MTT assay method. Most of the compounds significantly active among which 1d exhibited promising activity with IC50 values of 2.5, 4.8 and 5.4 μM specifically against hepatocellular liver carcinoma (HepG2), lung adenocarcinoma (A549) and prostate (DU‐145) cell lines, while compound 1j showed promising cytotoxicity against human breast

  合成，表征新型系列（）-儿茶素衍生物1a-1，并通过标准MTT分析方法测定其对四种选定的人类癌细胞系的细胞毒性。大多数化合物具有显着活性，其中1d表现出良好的活性，IC 50值分别为2.5、4.8和5.4μM，特别是针对肝细胞肝癌（HepG2），肺腺癌（A549）和前列腺（DU-145）细胞系，而化合物1j对人乳腺腺癌MDA-MB-231具有良好的细胞毒性（IC 50值为6.6μM）。化合物1a，1d，1e，1f和1j对所有筛选的细胞系均表现出广谱细胞毒性。化合物1d的分子对接研究建立了良好的结合亲和力，有利于观察到的生物活性。这些数据共同表明，化合物1d可以作为进一步优化抗癌剂的新模板。
• Structurally Constrained Hybrid Derivatives Containing Octahydrobenzo[<i>g</i> or <i>f</i>]quinoline Moieties for Dopamine D2 and D3 Receptors: Binding Characterization at D2/D3 Receptors and Elucidation of a Pharmacophore Model
  作者：Dennis A. Brown、Prashant S. Kharkar、Ingrid Parrington、Maarten E. A. Reith、Aloke K. Dutta

  DOI：10.1021/jm8008629

  日期：2008.12.25

  series of structurally constrained analogues based on hybrid compounds containing octahydrobenzo[g or f]quinoline moieties were designed, synthesized, and characterized for their binding to dopamine D2 and D3 receptors expressed in HEK-293 cells. Among the newly developed constrained molecules, trans-octahydrobenzo[f]quinolin-7-ol (8) exhibited the highest affinity for D2 and D3 receptors, the (-)-isomer

  设计、合成了一系列基于含有八氢苯并[g 或 f] 喹啉部分的杂化化合物的结构受限类似物，并表征了它们与 HEK-293 细胞中表达的多巴胺 D2 和 D3 受体的结合。在新开发的受限分子中，trans-octahydrobenzo[f]quinolin-7-ol (8) 对 D2 和 D3 受体表现出最高的亲和力，(-)-异构体是 eutomer。有趣的是，当在相同条件下（K(i) 为 49.1 和 14.9 nM，8 对比 380 和 96.0 nM，K(i) 为1 分别在 D2 和 D3）。其他先导杂化化合物也发现了类似的结果，表明哌嗪部分对观察到的增强亲和力的贡献。基于我们开发的新型铅约束衍生物和其他铅杂化衍生物的数据，提出了一个独特的药效团模型，由三个药效团中心组成，两个具有芳香/疏水性，一个具有阳离子特征。