4-哌啶酮，1-[（4-甲基苯基）磺酰基]- | 33439-27-9

• 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: 4-哌啶酮，1-[（4-甲基苯基）磺酰基]-
• 中文别名: 4-哌啶酮,1-[(4-甲基苯基)磺酰基]-
• 英文名称: N-tosyl-4-piperidone
• 英文别名: 1-tosylpiperidin-4-one；N-tosylpiperidin-4-one；1-(4-methylbenzenesulfonyl)piperidin-4-one；1-tosyl-4-piperidinone；1-tosylpiperidine-4-one；1-(4-methylphenyl)sulfonylpiperidin-4-one
• CAS: 33439-27-9
• 化学式: C₁₂H₁₅NO₃S
• mdl: MFCD00218704
• 分子量: 253.322
• InChiKey: PCEBUFJFSAZGNQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  >38 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存储条件：室温、密封且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Tosylpiperidin-4-one
Synonyms:

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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: 1-Tosylpiperidin-4-one
CAS number: 33439-27-9

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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: C12H15NO3S
Molecular weight: 253.3

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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, sulfur 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-哌啶酮，1-[（4-甲基苯基）磺酰基]- 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 1-tosyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  开发 2-叠氮基硼酸频哪酸酯和乙烯基三氟甲磺酸酯之间的 Suzuki 交叉偶联反应，以合成 [2,3]-稠合吲哚杂环

  摘要：

  报道了 2-叠氮基硼酸频哪酸酯和乙烯基三氟甲磺酸酯之间的 Suzuki 反应的范围和局限性。这种交叉偶联反应能够在随后的 Rh II 2催化的 sp 2 -C-H 键胺化反应后区域选择性地合成吲哚。

  DOI：

  10.1021/jo500252e
• 作为产物：
  描述：

  1-[(4-甲苯)磺酰基]-4-哌啶醇 在 亚碘酰苯 、 potassium bromide 作用下， 以 水 为溶剂， 反应 24.0h， 以86%的产率得到4-哌啶酮，1-[（4-甲基苯基）磺酰基]-
  参考文献：
  名称：

  使用高价碘 (III) 试剂轻松、清洁地氧化水中的醇

  摘要：

  描述了使用高价碘 (III) 试剂碘代苯 (PhI=O) 与 KBr 在水中轻松有效地氧化各种醇，例如苯甲醇、伯醇、仲醇和二醇。对水溶液中 PhI=O-KBr 行为的电喷雾电离 (ESI) 质谱研究表明，这些反应是由高活性碘物质 [PhI(Br)nO –] 的形成引起的。对可回收聚合物负载的碘 (III) 试剂的进一步开发扩展了该反应的实用性，从而提供了一种环境友好的方法。

  DOI：

  10.1002/1615-4169(200206)344:3/4<328::aid-adsc328>3.0.co;2-s
• 作为试剂：
  描述：

  4-piperidone monohydrochloride monohydrate 、 potassium carbonate 、 对甲苯磺酰氯 在 4-哌啶酮，1-[（4-甲基苯基）磺酰基]- 、 氯仿 、 Sodium sulfate-III 、 crude product 、 silica gel 作用下， 以 chloroform hydrate 为溶剂， 反应 4.0h， 生成 4-哌啶酮，1-[（4-甲基苯基）磺酰基]-
  参考文献：
  名称：

  Curcumin Analogs and Methods of Making and Using Thereof

  摘要：

  本文描述了具有I或II式的化合物及其制备和使用方法：

  公开号：

  US20150152056A1

文献信息

• Synthesis of novel 1,3-thiazin-4-ones by acetylene diester cyclization and their anticancer activities
  作者：Selvam Athavan Alias Anand、Chandrasekaran Loganathan、Nisha Susan Thomas、Kuppusamy Saravanan、Antony Therasa Alphonsa、Senthamaraikannan Kabilan

  DOI：10.1080/10426507.2016.1209502

  日期：2016.10.2

  synthesized efficiently by thioamide and acetylene diester cyclization reaction via aminolysis of the ester group and the elimination of an alcohol molecule. The structures of all the novel compounds were established by their FTIR, Mass, 1H NMR, and 13C NMR spectral techniques. The newly synthesized compounds (7–16) were studied for their in vitro anticancer activity against human liver cancer cell lines Hep

  图形摘要摘要通过硫代酰胺和乙炔二酯环化反应，通过酯基的氨解和醇的消除，设计并有效合成了一系列含有哌啶环 (7-16) 的新型 1,3-thiazin-4-one 衍生物。分子。所有新化合物的结构均通过 FTIR、Mass、1H NMR 和 13C NMR 光谱技术确定。使用 MTT 测定研究了新合成的化合物 (7-16) 对人肝癌细胞系 Hep G2 的体外抗癌活性。测试化合物的 IC50 值介于 7.48 ± 0.71 和 56.57 ± 1.37 µM 之间。此外，使用 JC-1 染料通过线粒体膜电位进行细胞凋亡评估，结果与细胞毒性研究非常一致。
• Methyl Radical Initiated Kharasch and Related Reactions
  作者：Nicholas D. C. Tappin、Philippe Renaud

  DOI：10.1002/adsc.202001000

  日期：2021.1.5

  chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di‐tert‐butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating

  据报道，一种改进的方法可以运行卤原子和相关的硫族基转移自由基。该程序依赖于二丁基亚硫酸氢盐（DTBHN）的热分解，后者是爆炸性二乙酰过氧化物的安全替代品，可产生可引发链过程的高反应性甲基。这种引发方式产生的副产物要么是气态的（N 2）或挥发性（丙酮和甲基卤化物），从而极大地促进了通过快速柱色谱或蒸馏的产物纯化。另外，非常简单和温和的反应条件（在常压下于30分钟内回流EtOAc）和少量过量的自由基前体试剂（2当量）使该方案对制备合成应用特别有吸引力。该引发程序已经得到了广泛的应用，因为它可以有效地将一系列由碘化物，溴化物，硒化物和黄药生成的亲电子基团添加到一系列未活化的末端烯烃上。多种自由基捕获底物集体现了广泛的官能团耐受性。最后，二叔过氧草酸丁酯（DTBPO）也被证明是叔丁氧基自由基的替代来源，可在相同条件下引发这些反应，产生气态副产物（CO 2）。
• Site‐Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes
  作者：James A. Law、Noah M. Bartfield、James H. Frederich

  DOI：10.1002/anie.202103278

  日期：2021.6.21

  Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp2Ti(μ-Cl)(μ-CH2)AlMe2

  甲基在生物活性分子中普遍存在。因此，将这种烷基片段引入多官能结构的新策略引起了人们的极大兴趣。考虑到这一目标，报告了一种烯烃马尔可夫尼科夫氢甲基化的直接方法。该方法利用了Cp 2 Ti(μ-Cl)(μ-CH 2 )AlMe 2 (Tebbe试剂)中的钛亚甲基与未活化的烯烃之间的简并复分解反应。所得环丁烷钛的原位质子解作用以化学、区域和位点选择性方式实现氢甲基化。该方法的广泛实用性在一系列含有侧醇、醚、酰胺、氨基甲酸酯和碱性胺的单取代和二取代烯烃中得到了证明。
• Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
  作者：Shun Wang、Bei-Yi Cheng、Matea Sršen、Burkhard König

  DOI：10.1021/jacs.0c00629

  日期：2020.4.22

  catalysis with the Wolff–Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff–Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles

  光氧化还原催化与沃尔夫-基什纳 (WK) 反应相结合，可以通过自由基-碳负离子中继序列（光沃尔夫-基什纳反应）对羰基进行双官能化。光氧化还原引发自由基加成至 N-磺酰腙，按照 WK 型机制产生 α-功能化碳负离子。对于以硫为中心的自由基，碳负离子通过与包括 CO2 和醛在内的亲电子试剂反应而进一步官能化，而 CF3 自由基加成则通过生成的 α-CF3 碳负离子的 β-氟化物消除提供了多种偕二氟烯烃。 80 多个底物示例证明了该反应序列的广泛适用性。包括自由基抑制、氘标记、荧光猝灭、循环伏安法和控制实验在内的一系列研究支持了所提出的自由基-碳负离子中继机制。
• Cobalt‐Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α‐Ketoamides
  作者：Tingting Li、Gerald B. Hammond、Bo Xu

  DOI：10.1002/chem.202101035

  日期：2021.7.7

  developed to synthesize ketones, esters, amides via the oxidative C−C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.

  开发了一种广泛适用的方法，通过容易获得的烷基醛的氧化 C-C 键裂解来合成酮、酯、酰胺。绿色且丰富的分子氧（O 2）用作氧化剂，贱金属（钴和铜）用作催化剂。该策略可以扩展到由伯醇合成酮和由醛合成α-酮酰胺的一锅法。