6-苯基哌啶-2,4-二酮 | 118264-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 6-苯基哌啶-2,4-二酮
• 中文别名: 6-苯基-2,4-哌啶二酮
• 英文名称: 6-phenylpiperidine-2,4-dione
• CAS: 118264-04-3
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD10568157
• 分子量: 189.214
• InChiKey: IBYLHJWZATWPEB-UHFFFAOYSA-N

物化性质

• 熔点：
  174.5-175.5 °C
• 沸点：
  440.1±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Phenylazaperhydroine-2,4-dione
Synonyms: 6-Phenyl-5,6-dihydro-2,4(1H,3H)-pyridinedione

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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: 6-Phenylazaperhydroine-2,4-dione
CAS number: 118264-04-3

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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: C11H11NO2
Molecular weight: 189.2

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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：

  6-苯基哌啶-2,4-二酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以38%的产率得到(4S,6S)-4-hydroxy-6-phenylpiperidin-2-one
  参考文献：
  名称：

  Ashton, Michael J.; Hills, Susan J.; Newton, Christopher G., Heterocycles, 1989, vol. 28, # 2, p. 1015 - 1035

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 吡啶 、 sodium hydroxide 、 草酰氯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6-苯基哌啶-2,4-二酮
  参考文献：
  名称：

  通过β-芳基-β-氨基酸的链延伸方便地合成6-芳基哌啶-2,4-二酮

  摘要：

  从β-芳基-β-氨基酸开始，经由后者的链扩展成δ-芳基-δ-氨基-β-酮酸的五个步骤描述了新的6-芳基哌啶-2，4-二酮的合成。该化学途径涉及梅德鲁姆酸的酰化作用，并产生了用于杂环化学的有用的结构单元。

  DOI：

  10.1016/s0040-4039(01)01991-8

文献信息

• COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：WIGEN BIOMEDICINE TECHNOLOGY (SHANGHAI) CO., LTD.

  公开号：US20200190066A1

  公开（公告）日：2020-06-18

  It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

  该内容涉及作为自噬调节剂的化合物及其制备和使用方法，具体提供了一类具有通用公式(I)的化合物，或其药用可接受盐，这是一种自噬调节剂，特别是哺乳动物ATG8同源物调节剂。
• A New Method of Synthesis of 6-Substituted Piperidine-2,4-diones from Homoallylamines
  作者：Nikolai Yu. Kuznetsov、Victor I. Maleev、Victor N. Khrustalev、Anna F. Mkrtchyan、Ivan A. Godovikov、Tatyana V. Strelkova、Yuri N. Bubnov

  DOI：10.1002/ejoc.201101114

  日期：2012.1

  triallylborane and enantiomerically enriched N-Boc-1-phenyl-3-butenylamine was synthesized by the addition of (–)-AllB(Ipc)2 to the corresponding silylimine. Chiral precursors containing a carboxylic ester group were synthesized from (S)-allylglycine and-alanine. The reactions of N-Boc derivatives with NBS smoothly produced the corresponding bromocyclocarbamates either in the form of a single diastereomer or

  单和二高烯丙基胺可作为制备 6-取代哌啶-2,4-二酮的方便前体。这种转变一方面基于简单且众所周知的卤代环氨基甲酸化反应，该反应通过将阳离子卤素源添加到 N-Boc 保护的高烯丙胺中进行，另一方面基于新的烯醇 - 异氰酸酯重排这是通过对溴环氨基甲酸酯的强碱的作用进行的。通过腈或伯酰胺与三烯丙基硼烷的烯丙基硼化反应制备了一组外消旋二高烯丙基胺，并通过将 (-)-AllB(Ipc)2 添加到相应的甲硅烷基亚胺中合成富含对映体的 N-Boc-1-苯基-3-丁烯胺. 含有羧酸酯基团的手性前体由 (S)-烯丙基甘氨酸和-丙氨酸合成。N-Boc 衍生物与 NBS 的反应顺利地产生了相应的溴环氨基甲酸酯，无论是单一非对映体形式还是异构体混合物。所有这些溴代氨基甲酸酯都通过形成中间体环状烯醇以良好的收率干净地转化为 6-取代的哌啶-2,4-二酮，这通过烯醇 12 的直接合成及其在一系列动力学实验中转化为二酮
• [EN] USE OF CONDENSED BENZO[B]THIAZINE DERIVATIVES AS CYTOPROTECTANTS<br/>[FR] UTILISATION DE DÉRIVÉS DE BENZO[B]THIAZINE EN TANT QU'AGENTS CYTOPROTECTEURS
  申请人：MEDEIA THERAPEUTICS LTD

  公开号：WO2014191632A1

  公开（公告）日：2014-12-04

  The present invention relates to arylthiazine compounds, metabolites, N-oxides, amides, esters,pharmaceutically acceptable salts, hydrates and solvates thereof and their use as cytoprotectants in the treatment or prophylaxis of diseases or states, either acute or chronic, involving aberrant cellular lipid peroxidation in the central nervous system or in the periphery of the body. The present invention also relates to a method for their preparation and to pharmaceutical composition comprising as an active ingredient one or more of the aforementioned compounds.

  本发明涉及芳基噻嗪化合物、代谢物、N-氧化物、酰胺、酯、药用可接受盐、水合物和溶剂合物，以及它们在治疗或预防涉及中枢神经系统或身体周围存在异常细胞脂质过氧化的疾病或状态中作为细胞保护剂的用途。本发明还涉及它们的制备方法以及包含作为活性成分的上述化合物之一或多个的药物组合物。
• Structure−Activity Relationship Study of First Selective Inhibitor of Excitatory Amino Acid Transporter Subtype 1: 2-Amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4<i>H</i>-chromene-3-carbonitrile (UCPH-101)
  作者：Mette N. Erichsen、Tri H. V. Huynh、Bjarke Abrahamsen、Jesper F. Bastlund、Christoffer Bundgaard、Olja Monrad、Anders Bekker-Jensen、Christina W. Nielsen、Karla Frydenvang、Anders A. Jensen、Lennart Bunch

  DOI：10.1021/jm1009154

  日期：2010.10.14

  The excitatory amino acid transporters (EAATs) are expressed throughout the central nervous system, where they are responsible for the reuptake of the excitatory neurotransmitter (S)-glutamate (Glu).(1) Recently, we have reported the discovery of the first subtype selective EAAT1 inhibitor 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101)

  兴奋性氨基酸转运蛋白（EAAT）在整个中枢神经系统中表达，它们负责兴奋性神经递质（S）-谷氨酸（Glu）的再摄取。（1）最近，我们报道了第一个亚型的发现。选择性EAAT1抑制剂2-氨基-4-（4-甲氧基苯基）-7-（萘-1-基）-5-氧代-5,6,7,8-四氢-4 H-亚甲基-3-腈（UCPH- 101）（1b）并进行了结构-活性关系（SAR）的入门研究。（2）在这里，我们通过类似物1g - 1t的设计，合成和药理学评估给出了详细的SAR 。通过比较1b，1h和1i的效能与1j相比，很明显，效力很大程度上受R 1取代基的化学性质影响。该研究还表明，官能团的任何化学变化或亲本支架的变化都会导致化合物在EAAT1处的抑制活性完全丧失。最终，UCPH-101的生物利用度研究确定其在血清（大鼠）中的半衰期为30分钟，但它也无法显着穿透血脑屏障。
• Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations
  作者：Charles M. Marson、Kin Cheung Yau

  DOI：10.1016/j.tet.2015.06.052

  日期：2015.9

  A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

  描述了一种柔性路线，该路线可得到在6-，5,6-和2,6-位被1和2取代的哌啶-2,4-二酮，无论有无取代。不需要氮保护基。还描述了相关的区域选择性Dieckmann环化反应，该环化反应使用戴维斯的α-甲基苄胺助剂，并选择性地提供6-取代的哌啶-2,4-二酮。