4-(4-羧基苯基)哌嗪-1-羧酸叔丁酯 | 162046-66-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 哌嗪类化合物
• 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-(4-羧基苯基)哌嗪-1-羧酸叔丁酯
• 中文别名: 4-(4-羧基苯基)哌嗪-1-甲酸酸叔丁酯；4-(4-Boc-哌嗪基)苯甲酸；4-[4-BOC-哌嗪基]苯甲酸
• 英文名称: 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzoic acid
• 英文别名: 4-(4-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester；4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)benzoic acid；4-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]benzoic acid
• CAS: 162046-66-4
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: BEDWYXZFIYMEJG-UHFFFAOYSA-N

物化性质

• 熔点：
  50 °C
• 沸点：
  476.9±40.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：室温、干燥密封

SDS

Name:	4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid Material Safety Data Sheet
Synonym:	None Known
CAS:	162046-66-4

Section 1 - Chemical Product MSDS Name:4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
162046-66-4	4-[4-(tert-Butoxycarbonyl)piperazino]b	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
No information found.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 162046-66-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Crystalline powder
Color: White
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 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: C16H22N2O4
Molecular Weight: 306.36

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 162046-66-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid - 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: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
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.
WGK (Water Danger/Protection)
CAS# 162046-66-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 162046-66-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 162046-66-4 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

制备方法与用途

Boc哌嗪苯甲酸是一种PROTAC连接剂，可用于合成如雄激素受体（AR）降解剂ARD-2128（HY-13229）等PROTAC。

反应信息

• 作为反应物：
  描述：

  4-(4-羧基苯基)哌嗪-1-羧酸叔丁酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.67h， 以85%的产率得到Tert-butyl 4-(4-carbamoylphenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  WO2008/148840

  摘要：

  公开号：
• 作为产物：
  描述：

  4-(1-哌嗪基)苯甲酸乙酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 9.0h， 生成 4-(4-羧基苯基)哌嗪-1-羧酸叔丁酯
  参考文献：
  名称：

  Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part 1: Design and synthesis of a lead compound exhibiting αvβ3/αIIbβ3 dual antagonistic activity

  摘要：

  In order to generate novel compounds with integrin alpha(v)beta(3)-antagonistic activity together with antiplatelet activity, tricyclic pharmacophore-based molecules were designed and synthesized. Although piperazine-containing compounds initially prepared were selective alpha(IIb)beta(3) antagonists, replacement of piperazine with piperidine furnished a potent alpha(v)beta(3)/alpha(IIb)beta(3) dual antagonist. Structureactivity relationship (SAR) studies provided clues for further development of tricyclic pharmacophore-based integrin antagonists. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.060

文献信息

• [EN] MODULATORS OF HCV REPLICATION<br/>[FR] MODULATEURS DE LA REPLICATION DE HCV
  申请人：ANGELETTI P IST RICHERCHE BIO

  公开号：WO2006038039A1

  公开（公告）日：2006-04-13

  The present invention is directed to the use of compounds of formula (I): 1 R X 3 R Y ( I) 2 R 5 where X, Y, R1, R2 and R3 are defined therein, which can act as modulators of viral replication and/or virus production, especially of the hepatitis C virus (HCV), in a cell based system.

  本发明涉及使用式(I)的化合物：1 R X 3 R Y ( I) 2 R 5，其中X、Y、R1、R2和R3在其中被定义，这些化合物可以作为病毒复制和/或病毒产生的调节剂，特别是对丙型肝炎病毒（HCV）在基于细胞的系统中。
• [EN] OXADIAZOLE INHIBITORS OF LEUKOTRIENE PRODUCTION<br/>[FR] COMPOSÉS OXADIAZOLE, INHIBITEURS DE LA PRODUCTION DE LEUCOTRIÈNES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012027322A1

  公开（公告）日：2012-03-01

  The present invention relates to compound of formula (I) and pharmaceutically acceptable salt thereof, wherein R1-R5 are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本发明涉及式(I)的化合物及其药用可接受盐，其中R1-R5如本文所定义。该发明还涉及包括这些化合物的药物组合物，使用这些化合物治疗各种疾病和疾病的方法，制备这些化合物的过程以及在这些过程中有用的中间体。
• COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF ANDROGEN RECEPTOR
  申请人：Arvinas, Inc.

  公开号：US20180099940A1

  公开（公告）日：2018-04-12

  The present disclosure relates to bifunctional compounds, which find utility to degrade and (inhibit) Androgen Receptor. In particular, the present disclosure is directed to compounds, which contain on one end a cereblon ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds Androgen Receptor, such that Androgen Receptor is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of Androgen Receptor. The present disclosure exhibits a broad range of pharmacological activities associated with compounds according to the present disclosure, consistent with the degradation/inhibition of Androgen Receptor.

  本公开涉及双功能化合物，其用于降解和（抑制）雄激素受体。具体而言，本公开涉及包含一端结合到E3泛素连接酶的谷氨酰腺苷环配体，另一端结合到雄激素受体的部分的化合物，使得雄激素受体与泛素连接酶靠近，以实现雄激素受体的降解（和抑制）。本公开展示了与根据本公开涉及的化合物相关的广泛的药理活性范围，与雄激素受体的降解/抑制一致。
• Sulfonamide derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06359134B1

  公开（公告）日：2002-03-19

  The present invention provides compounds which specifically inhibit FXa, which are effective when orally administered and which are useful as a safe medicine for the prevention or treatment of diseases caused by thrombus or infarction. Compounds of this invention are piperazinones of the formula: wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; the ring A is an optionally substituted divalent nitrogen-containing heterocyclic group, in addition to being substituted by the group of the formula: and the group of the formula: Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent heterocyclic group; X is a direct bond or an optionally substituted alkylene chain; Z is (1) an amino group substituted with an optionally substituted hydrocarbon group, (2) an optionally substituted imino group or (3) an optionally substituted nitrogen-containing heterocyclic group; provided that when X is a direct bond and Z is an optionally substituted 6-membered nitrogen-containing aromatic heterocyclic group, Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent unsaturated heterocyclic group; or a salt thereof.

  本发明提供了一种化合物，该化合物特异性地抑制FXa，口服给药有效，并且用作预防或治疗由血栓或梗死引起的疾病的药物是安全的。本发明的化合物是哌嗪酮的公式： 其中R1是可选地取代的烃基或可选地取代的杂环基；环A是除了被公式：的基团取代的之外的可选地取代的二价含氮杂环基： 和公式的基团： Y是可选地取代的二价烃基或可选地取代的二价杂环基；X是直接键或可选地取代的亚烷基链；Z是（1）与可选地取代的烃基取代的氨基，（2）可选地取代的亚氨基或（3）可选地取代的含氮杂环基；当X是直接键并且Z是可选地取代的6-成员含氮芳香杂环基时，Y是可选地取代的二价烃基或可选地取代的二价不饱和杂环基；或其盐。
• Fibrinogen receptor antagonists
  申请人：Merck & Co., Inc.

  公开号：US05780480A1

  公开（公告）日：1998-07-14

  Fibrinogen receptor antagonists of the general formula: X-A-Y-Z-B I and which includes, for example, the compounds of formula ##STR1## are useful for inhibiting the binding of fibrinogen to blood platelets, inhibiting the aggregation of blood platelets, treating thrombus formation or embolus formation, and preventing thrombus or embolus formation.

  一般公式为：X-A-Y-Z-B的纤维蛋白原受体拮抗剂，例如包括公式##STR1##的化合物，可用于抑制纤维蛋白原与血小板的结合，抑制血小板聚集，治疗血栓形成或栓塞形成，并预防血栓或栓塞形成。