3-(4-硝基苯氧基羰基)-2,2,5,5-四甲基-1-吡咯烷基氧化物 | 21913-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 3-(4-硝基苯氧基羰基)-2,2,5,5-四甲基-1-吡咯烷基氧化物
• 英文名称: 3-carboxyl-PROXYL p-nitrophenyl ester
• 英文别名: 3-carboxy-PROXYL p-nitrophenyl ester；p-nitrophenyl proxyl-3-carboxylate；p-nitrophenyl-PROXYL-3-carboxylate；3-(4-Nitrophenoxycarbonyl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy
• CAS: 21913-97-3
• 化学式: C₁₅H₁₉N₂O₅
• 分子量: 307.326
• InChiKey: LJQNUWWVYJMKTA-UHFFFAOYSA-N

物化性质

• 熔点：
  77-80 °C
• 沸点：
  447.83°C (rough estimate)
• 密度：
  1.1846 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25

SDS

Name:	3-(4-Nitrophenoxycarbonyl)-Proxyl Free Radical 98% Material Safety Data Sheet
Synonym:	3-(4-Nitrophenoxycarbonyl)-2,2,5,5-Tetramethyl-1-Pyrrolidinyloxy
CAS:	21913-97-3

Section 1 - Chemical Product MSDS Name:3-(4-Nitrophenoxycarbonyl)-Proxyl Free Radical 98% Material Safety Data Sheet
Synonym:3-(4-Nitrophenoxycarbonyl)-2,2,5,5-Tetramethyl-1-Pyrrolidinyloxy

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
21913-97-3	3-(4-Nitrophenoxycarbonyl)-Proxyl, Fre	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. 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.
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:

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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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.)

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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# 21913-97-3: 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 minimize contact with skin.
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: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 77.00 - 80.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C15H19N2O5
Molecular Weight: 307.32

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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, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 21913-97-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(4-Nitrophenoxycarbonyl)-Proxyl, Free Radical - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 21913-97-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 21913-97-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 21913-97-3 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：

  、 3-(4-硝基苯氧基羰基)-2,2,5,5-四甲基-1-吡咯烷基氧化物 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 3-((12-((4-methyl-2-oxo-2H-chromen-7-yl)thio)dodecyl)oxy)-2-(12'-((1"-pyrrolidinyloxy-3"-carboxy)dodecyl)oxy)-3-oxopropyl phosphocholine
  参考文献：
  名称：

  甘油酸支架上磷脂的合成：磷脂酶 A2 特异性底物的设计和制备

  摘要：

  合成了一系列新的磷脂类似物，用作分泌型磷脂酶 A 2酶的活性探针。该合成基于 (1) 甘油酸的长链酯和酰胺的制备，然后 (2) 分子的二醇官能团的区域选择性衍生化以实现伯羟基的磷酸化，并引入初始的sn -目标化合物的2-酯基团。该序列已被证明允许掺入荧光、顺磁性和氧化还原活性报告基团，从而产生适用于检测和测量酶活性的磷脂类似物，以开发高度特异性、实时的磷脂酶 A 2光谱分析酶，以及跟踪水解产物的代谢归宿。该合成方法具有很大的灵活性，为其他磷脂代谢酶的活性探针的设计和合成开辟了道路。

  DOI：

  10.1016/j.tet.2014.03.054
• 作为产物：
  描述：

  对硝基苯酚 、 3-羧基-PROXYL 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 以83.8%的产率得到3-(4-硝基苯氧基羰基)-2,2,5,5-四甲基-1-吡咯烷基氧化物
  参考文献：
  名称：

  A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of l-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives

  摘要：

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.

  DOI：

  10.1021/jo990414e

文献信息

• Synthesis of phosphatidylcholine analogues derived from glyceric acid: a new class of biologically active phospholipid compounds
  作者：Renato Rosseto、Celize M. Tcacenco、Radha Ranganathan、Joseph Hajdu

  DOI：10.1016/j.tetlet.2008.03.084

  日期：2008.5

  Synthesis of a new class of phosphatidylcholine analogues derived from glyceric acid is reported for spectroscopic studies of phospholipases and conformation of phospholipid side-chains in biological membranes, using fluorescence resonance energy transfer (FRET) techniques.

  据报道，使用荧光共振能量转移 (FRET) 技术合成了一类新的源自甘油的磷脂酰胆碱类似物，用于磷脂酶和生物膜中磷脂侧链构象的光谱研究。
• A rapid and efficient method for migration-free acylation of lysophospholipids: synthesis of phosphatidylcholines with sn-2-chain-terminal reporter groups
  作者：Renato Rosseto、Joseph Hajdu

  DOI：10.1016/j.tetlet.2005.02.150

  日期：2005.4

  A rapid and efficient method for migration-free acylation of lysophosphatidylcholines has been developed using ultrasound for agitation of the reaction mixture and glass beads for increasing the surface in the reaction vessel. The products were obtained in good yields and short reaction times. The method has been applied for the preparation of a variety of substituted phospholipid substrates. (c) 2005 Published by Elsevier Ltd.
• A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of <scp>l</scp>-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives
  作者：Farzaneh S. Roodsari、Dongpei Wu、Gregory S. Pum、Joseph Hajdu

  DOI：10.1021/jo990414e

  日期：1999.10.1

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.
• Synthesis of phospholipids on a glyceric acid scaffold: design and preparation of phospholipase A2 specific substrates
  作者：Renato Rosseto、Joseph Hajdu

  DOI：10.1016/j.tet.2014.03.054

  日期：2014.5

  Synthesis of a new series of phospholipid analogues to serve as activity-based probes of secretory phospholipase A2 enzymes is reported. The synthesis is based upon (1) preparation of long-chain esters and amides of glyceric acid, followed by (2) regioselective derivatization of the diol function of the molecule to achieve phosphorylation at the primary hydroxyl group, and to introduce the incipient

  合成了一系列新的磷脂类似物，用作分泌型磷脂酶 A 2酶的活性探针。该合成基于 (1) 甘油酸的长链酯和酰胺的制备，然后 (2) 分子的二醇官能团的区域选择性衍生化以实现伯羟基的磷酸化，并引入初始的sn -目标化合物的2-酯基团。该序列已被证明允许掺入荧光、顺磁性和氧化还原活性报告基团，从而产生适用于检测和测量酶活性的磷脂类似物，以开发高度特异性、实时的磷脂酶 A 2光谱分析酶，以及跟踪水解产物的代谢归宿。该合成方法具有很大的灵活性，为其他磷脂代谢酶的活性探针的设计和合成开辟了道路。