4-(3-硝基吡啶-2-基)-哌嗪-1-甲酸叔丁酯 | 153473-24-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 4-(3-硝基吡啶-2-基)-哌嗪-1-甲酸叔丁酯
• 中文别名: 1-Boc-4-(3-硝基吡啶-2-基)哌嗪
• 英文名称: 1-tert-butoxycarbonyl-4-(3-nitro-2-pyridyl)piperazine
• 英文别名: 3-nitro-2-(Boc-piperazinyl)pyridine；4-(3-nitropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester；tert-butyl 4-(3-nitropyridin-2-yl)piperazine-1-carboxylate
• CAS: 153473-24-6
• 化学式: C₁₄H₂₀N₄O₄
• mdl: MFCD09028514
• 分子量: 308.337
• InChiKey: FXKKCZGSSAXGMV-UHFFFAOYSA-N

物化性质

• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 安全说明：
  S45
• 危险类别码：
  R25
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4-BOC-Piperazino)-3-nitropyridine
Synonyms: 4-(3-Nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl 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: 2-(4-BOC-Piperazino)-3-nitropyridine
CAS number: 153473-24-6

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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.
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: C14H20N4O4
Molecular weight: 308.3

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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：

  4-(3-硝基吡啶-2-基)-哌嗪-1-甲酸叔丁酯 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 1-((1,1-二甲基乙氧基)羰基)-4-(3-((1-甲基乙基)氨基)-2-吡啶)哌嗪
  参考文献：
  名称：

  带有芳基吡咯部分的新delavirdine类似物的合成和抗HIV-1活性。

  摘要：

  在我们寻找新型抗人免疫缺陷病毒（HIV）-1药物的过程中，合成了14种地拉维定类似物，并在基于细胞的测定中评估为潜在的抗HIV-1药物。化合物1Aa在急性感染的MT4细胞中表现出有效的和选择性的抗HIV-1活性，其有效浓度（EC50）值在亚微摩尔范围内。

  DOI：

  10.1248/cpb.49.1406
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-(3-硝基吡啶-2-基)-哌嗪-1-甲酸叔丁酯
  参考文献：
  名称：

  带有芳基吡咯部分的新delavirdine类似物的合成和抗HIV-1活性。

  摘要：

  在我们寻找新型抗人免疫缺陷病毒（HIV）-1药物的过程中，合成了14种地拉维定类似物，并在基于细胞的测定中评估为潜在的抗HIV-1药物。化合物1Aa在急性感染的MT4细胞中表现出有效的和选择性的抗HIV-1活性，其有效浓度（EC50）值在亚微摩尔范围内。

  DOI：

  10.1248/cpb.49.1406

文献信息

• [EN] FGFR2 MODULATORS<br/>[FR] MODULATEURS DE FGFR2
  申请人：EXELIXIS INC

  公开号：WO2012061337A1

  公开（公告）日：2012-05-10

  A compound of Formula (I), or a pharmaceutically acceptable salt thereof, wherein:R3a, R2, R3b, R4b, L1, G and J are as defined in the specification, pharmaceutical compositionsthereof, and methods of use thereof.

  一个由化学式（I）组成的化合物，或其药学上可接受的盐，其中：R3a、R2、R3b、R4b、L1、G和J的定义如规范中所述，以及其药物组成物和使用方法。
• 一种制备1-叔丁氧羰基-4-[3-(烷基胺基)-2-吡啶基]哌嗪的方法
  申请人：吉林大学

  公开号：CN109776403B

  公开（公告）日：2022-06-14

  一种制备1‑叔丁氧羰基‑4‑[3‑(烷基胺基)‑2‑吡啶基]哌嗪的方法，属于有机化学制备技术领域。本发明是将1‑叔丁氧羰基‑4‑(3‑硝基‑2‑吡啶基)哌嗪、催化剂、助催化剂和烷基酮混合，加入耐压釜中；依次用氮气、氢气置换耐压釜内空气，然后再继续通入氢气进行反应；将反应体系降至室温，过滤，分去下层水层，上层有机层干燥后过滤除去干燥剂，蒸馏浓缩，重结晶后得到目标产物。本发明以1‑叔丁氧羰基‑4‑(3‑硝基‑2‑吡啶基)哌嗪为起始原料，在烷基酮、催化剂、氢气存在条件下进行还原烷基化反应，在同一个反应器中制备1‑叔丁氧羰基‑4‑[3‑(烷基胺基)‑2‑吡啶基]哌嗪。该方法具有操作简便、收率高的特点。
• Bicyclic heteroarylpiperazines as selective brain penetrant 5-HT6 receptor antagonists
  作者：Mahmood Ahmed、Michael A. Briggs、Steven M. Bromidge、Tania Buck、Lorraine Campbell、Nigel J. Deeks、Ashley Garner、Laurie Gordon、Dieter W. Hamprecht、Vicky Holland、Christopher N. Johnson、Andrew D. Medhurst、Darren J. Mitchell、Stephen F. Moss、Jenifer Powles、Jon T. Seal、Tania O. Stean、Geoffrey Stemp、Mervyn Thompson、Brenda Trail、Neil Upton、Kim Winborn、David R. Witty

  DOI：10.1016/j.bmcl.2005.06.107

  日期：2005.11

  Starting from the potent and selective but poorly brain penetrant 5-HT6 receptor antagonist SB-271046, a successful strategy for improving brain penetration was adopted involving conformational constraint with concomitant reduction in hydrogen bond count. This provided a series of bicyclic heteroarylpiperazines with high 5-HT6 receptor affinity. 5-Chloroindole 699929 combined high 5-HT6 receptor affinity with

  从有效且选择性强但对脑渗透性差的5-HT6受体拮抗剂SB-271046开始，采用了一种成功的提高脑部渗透性的策略，该方法涉及构象约束并伴随着氢键数的减少。这提供了一系列具有高5-HT 6受体亲和力的双环杂芳基哌嗪。5-氯吲哚699929结合了高5-HT6受体亲和力和出色的脑渗透性，并且在大鼠和狗中都具有良好的口服生物利用度。
• Oligomer modified diaromatic substituted compounds
  申请人：Riggs-Sauthier Jennifer

  公开号：US09226970B2

  公开（公告）日：2016-01-05

  Disclosed are compounds comprising diaromatic substituted compound residues, namely the anti-viral (anti-HIV) drug delavirdine, covalently attached via a linkage to water-soluble, non-peptidic oligomers, specifically to poly(ethylene glycol) (PEG) oligomers. A compound of the invention, when administered by any of a number of administration routes, exhibits advantages over non-oligomer modified diaromatic substituted compounds.

  本文披露了包含二芳基取代化合物残基的化合物，即抗病毒（抗HIV）药物德拉维林，通过连接共价附着到水溶性、非肽的寡聚物，具体是聚乙二醇（PEG）寡聚物。根据本发明的化合物，通过多种给药途径中的任何一种给药，相比未寡聚物修饰的二芳基取代化合物具有优势。
• Strategy for 14C-labeling of a series of bis(heteroaryl)piperazines
  作者：Omid Khalili Arjomandi、Nader Saemian、Gholamhossein Shirvani、Mohsen Javaheri、Kameh Esmailli

  DOI：10.1002/jlcr.1880

  日期：2011.6.15

  Four bis(heteroaryl)piperazines labeled with carbon-14 in the 2-position of imidazole moiety were prepared as part of a 4-step (or 5-step) sequence from 5-hydroxymethyl-2-mercapto-1-benzylimida-zole-[2-14C] as a key synthetic intermediate which has been synthesized from potassium [14C]-thiocyanate. Copyright © 2011 John Wiley & Sons, Ltd.

  本研究以 5-羟甲基-2-巯基-1-苄基咪唑-[2-14C]为关键合成中间体，通过 4 步（或 5 步）序列制备了四种在咪唑分子的 2 位上标记有碳-14 的双（杂芳基）哌嗪，该中间体是由[14C]-硫氰酸钾合成的。Copyright © 2011 John Wiley & Sons, Ltd. 版权所有。