1,5-二氢-4-(苯基甲氧基)-(2H)-吡咯-2-酮 | 113896-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,5-二氢-4-(苯基甲氧基)-(2H)-吡咯-2-酮
• 英文名称: 4-benzyloxy-1,5-dihydropyrrol-2-one
• 英文别名: 4-(benzyloxy)-1H-pyrrol-2(5H)-one；4-benzyloxy-3-pyrrolidin-2-one；4-benzyloxy-3-pyrrolin-2-one；4-Benzyloxy-3-pyrrolin-2-on；3-phenylmethoxy-1,2-dihydropyrrol-5-one
• CAS: 113896-95-0
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD00071563
• 分子量: 189.214
• InChiKey: FIPLVTFTJOOADU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Name:	4-Benzyloxy-3-Pyrrolin-2-One ca. 93%(TLC) Material Safety Data Sheet
Synonym:	None known
CAS:	113896-95-0

Section 1 - Chemical Product MSDS Name:4-Benzyloxy-3-Pyrrolin-2-One ca. 93%(TLC) Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
113896-95-0	4-Benzyloxy-3-Pyrrolin-2-One	ca 93	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.
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:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 113896-95-0: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: off-white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 147 - 151 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: C11H10NO2
Molecular Weight: 188.21

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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.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 113896-95-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Benzyloxy-3-Pyrrolin-2-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
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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 113896-95-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 113896-95-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 113896-95-0 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：

  1,5-二氢-4-(苯基甲氧基)-(2H)-吡咯-2-酮 以 四氢呋喃 、 palladium-carbon 为溶剂， 生成 2,4-吡咯烷二酮
  参考文献：
  名称：

  Synthesis of tetramic acid

  摘要：

  4-苄氧基-3-吡咯烯-2-酮是生产四元酸的一种新的有价值的中间产物。本文描述了生产这种中间产物以及四元酸的过程。

  公开号：

  US04812578A1
• 作为产物：
  描述：

  4-Benzyloxy-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙基苯 为溶剂， 反应 1.0h， 以80%的产率得到1,5-二氢-4-(苯基甲氧基)-(2H)-吡咯-2-酮
  参考文献：
  名称：

  Chemoselective Radical Cleavage of Cbz-Protected Nitrogen Compounds

  摘要：

  [GRAPHICS]Tributylstannyl radicals promote the deprotection of N-Cbz derivatives of amides and nitrogen-containing heteroaromatic rings. These radical conditions do not affect N-Cbz derivatives of basic amines.

  DOI：

  10.1021/ol027495c

文献信息

• A radical approach to N-desulfonylation
  作者：Andrew F. Parsons、Robert M. Pettifer

  DOI：10.1016/0040-4039(96)00086-x

  日期：1996.3

  The deprotection of N-sulfonylated amides can be achieved under neutral conditions by reaction with tributylin hydride. Good yields are obtained using N-benzoyl and related amides while the corresponding N-acetyl derivatives are inert under the same reaction conditions. The mechanistic implications of this are discussed.

  N-磺酰化酰胺的脱保护可以在中性条件下通过与氢化三丁基锡反应来实现。使用N-苯甲酰基和相关的酰胺可获得良好的收率，而在相同的反应条件下相应的N-乙酰基衍生物是惰性的。讨论了其机械含义。
• Desulfonylation of Amides Using Samarium Iodide
  作者：Haydn Knowles、Andrew Parsons、Robert Pettifer

  DOI：10.1055/s-1997-771

  日期：1997.3

  The desulfonylation of N-sulfonyl amides can be achieved in reasonable to excellent yield by reaction with samarium(II) iodide (SmI2) in THF at room temperature. Deprotection of acyclic and cyclic amides bearing aryl and alkylsulfonyl groups is possible.

  N-磺酰基酰胺的去磺酰化反应可通过在室温下与碘化镧(II) (SmI2)在THF中反应实现，产率从合理到优良均可。对带有芳基和烷基磺酰基的非环状和环状酰胺的去保护也是可行的。
• Direct <i>N</i>-Cyclopropylation of Cyclic Amides and Azoles Employing a Cyclopropylbismuth Reagent
  作者：Alexandre Gagnon、Miguel St-Onge、Kelly Little、Martin Duplessis、Francis Barabé

  DOI：10.1021/ja0676758

  日期：2007.1.1

  Cyclopropanes are commonly found in medicinal chemistry since they provide unique spatial and electronic features, combined with high metabolic stability in liver microsomes. Although many methods are found in the chemist's arsenal to connect a cyclopropyl group to a carbon atom, none exist that perform the direct transfer of this useful fragment onto the nitrogen of a heterocycle or an amide. Considering

  环丙烷在药物化学中很常见，因为它们提供独特的空间和电子特征，并结合肝微粒体中的高代谢稳定性。尽管在化学家的武器库中发现了许多将环丙基连接到碳原子的方法，但没有一种方法可以将这个有用的片段直接转移到杂环或酰胺的氮上。考虑到含氮化合物在制药行业中的重要性，我们寻求开发一种方便的方法来 N-环丙基化唑类和酰胺类。我们在此报告了使用非自燃性环丙基铋试剂对环酰胺、靛红、羟吲哚、酰亚胺和氨基甲酸酯进行的直接环丙基转移反应。该反应由乙酸铜催化，在 50 °C 的二氯甲烷中，在吡啶存在下顺利进行。N-环丙基化反应也可用于制备N-环丙基吲哚、苯并咪唑、吡咯和吡唑。
• Influence of B-ring modifications on proton affinity, transmembrane anion transport and anti-cancer properties of synthetic prodigiosenes
  作者：Estelle Marchal、Soumya Rastogi、Alison Thompson、Jeffery T. Davis

  DOI：10.1039/c4ob01399a

  日期：——

  We describe how modulating the pK_aof a family of synthetic prodigiosenes, modified on their B-ring, can control the transmembrane transport of anions.

  我们描述了如何调节一系列合成红色素家族的pK_a，通过修改它们的B环，可以控制阴离子的跨膜转运。
• Synthesis and Immunosuppressive Activity of Novel Prodigiosin Derivatives
  作者：Roberto D'Alessio、Alberto Bargiotti、Orlando Carlini、Francesco Colotta、Mario Ferrari、Paola Gnocchi、Annamaria Isetta、Nicola Mongelli、Pietro Motta、Arsenia Rossi、Mario Rossi、Marcello Tibolla、Ermes Vanotti

  DOI：10.1021/jm001003p

  日期：2000.6.1

  immunomodulating properties of this family of compounds we initiated a medicinal chemistry program aimed at finding novel prodigiosin derivatives with improved immunosuppressive activity and lower toxicity. Utilizing an unprecedented and flexible way of assembling the prodigiosin frame, a number of new derivatives have been prepared and tested leading to the choice of 4-benzyloxy-5-[(5-undecyl-2H-p

  靛红素（Ps）代表一族天然存在的红色颜料，其特征是具有常见的吡咯基吡咯甲烯骨架。已显示该家族的某些成员具有有趣的免疫抑制特性，该特性具有新颖的作用机制，与目前使用的药物不同。实际上，Ps抑制了JAK-3的磷酸化和激活，JAK-3是一种与细胞表面受体成分有关的细胞质酪氨酸激酶，该成分称为共同的γ链，不包括所有IL-2细胞因子家族受体。阻断共同的γ链转导活性导致有效的和特异性的免疫抑制活性。关于该化合物家族的有趣且尚未开发的免疫调节特性，我们发起了一项医学化学计划，旨在寻找具有改善的免疫抑制活性和较低毒性的新型prodigiosin衍生物。利用前所未有的灵活方式组装prodigiosin框架，已制备并测试了许多新的衍生物，从而导致选择4-苄氧基-5-[（5-十一烷基-2H-吡咯-2-亚甲基）甲基]- 2，2'-bi-1H-吡咯（PNU-156804，16）作为先导免疫抑制剂。