1-(四氢-2H-吡喃-4-基)乙酮 | 137052-08-5

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 1-(四氢-2H-吡喃-4-基)乙酮
• 中文别名: 4-乙酰四氢吡喃
• 英文名称: 1-(tetrahydro-2H-pyran-4-yl)ethan-1-one
• 英文别名: 1-(tetrahydro-2H-pyran-4-yl)ethanone；1-tetrahydropyran-4-ylethanone；4-acetyltetrahydropyran；1-(oxan-4-yl)ethanone
• CAS: 137052-08-5
• 化学式: C₇H₁₂O₂
• mdl: MFCD08704647
• 分子量: 128.171
• InChiKey: VNMXIOWPBADSIC-UHFFFAOYSA-N

物化性质

• 沸点：
  90-94℃/15mm
• 密度：
  1.024

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 危险品标志：
  Xn
• 危险类别码：
  R42,R36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(Tetrahydro-2H-pyran-4-yl)ethanone
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-(Tetrahydro-2H-pyran-4-yl)ethanone
CAS number: 137052-08-5

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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, refrigerated.
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: C7H12O2
Molecular weight: 128.2

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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.

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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

制备方法与用途

应用

1-(四氢-2H-吡喃-4-基)乙酮主要用作有机合成和医药化学的中间体，可用于细胞生物学检测试剂的合成。在有机合成中，该化合物中的酮羰基可以与Wittig试剂反应生成各种多取代烯烃；此外，酮羰基也可以通过相应的还原剂被还原成羟基。

制备

将N-甲氧基-N-甲基四氢-2H-吡喃-4-甲酰胺（1.7克，67.5毫摩尔）和四氢呋喃（350毫升）加入干燥的反应烧瓶中，并在冷井中浸入至-60度。8分钟内通过注射器逐滴滴加甲基溴化镁（3.0摩尔/乙醚，33.8毫升），随后将冷井温度缓慢升至0度并保持6小时。接着用水和乙酸乙酯稀释反应物，并剧烈搅拌10分钟后进行分相处理。水层用乙酸乙酯萃取，合并有机层并用盐水洗涤，干燥后过滤浓缩。残余物通过柱色谱法分离纯化即可得到目标产物分子1-(四氢-2H-吡喃-4-基)乙酮。

反应信息

• 作为反应物：
  描述：

  1-(四氢-2H-吡喃-4-基)乙酮 在 溴 作用下， 以 乙醚 为溶剂， 生成 2-溴-1-(四氢-吡喃-4-基)-乙酮
  参考文献：
  名称：

  Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates

  摘要：

  在此，我们报告了一种钯催化的乙烯基碳酸酯可控环化方法，该方法在温和条件下分别通过形式迁移 [2+3] 和 [5+2] 环加成反应进行。

  DOI：

  10.1039/c8cc06945j
• 作为产物：
  描述：

  N-甲氧基-n-甲基四氢吡喃-4-羧酰胺 在 甲基溴化镁 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 1-(四氢-2H-吡喃-4-基)乙酮
  参考文献：
  名称：

  PENTAFLUOROSULFUR IMINO HETEROCYCLIC COMPOUNDS AS BACE-1 INHIBITORS, COMPOSITIONS AND THEIR USE

  摘要：

  在它的许多实施例中，本发明提供了特定的五氟硫酰亚胺杂环化合物，包括式（a）的化合物及其药学上可接受的盐。式（a）的化合物具有以下一般结构：（a），其中每个变量是独立选择且如此定义的。本发明还揭示了包含一个或多个此类化合物（单独和与一个或多个其他活性剂的组合）的制药组合物，并用于治疗与淀粉样β（Aβ）蛋白相关的病理状况，包括阿尔茨海默病的方法。

  公开号：

  US20120195881A1

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES AS BROMODOMAIN INHIBITORS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE COMME INHIBITEURS DES BROMODOMAINES
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016146738A1

  公开（公告）日：2016-09-22

  Compounds of formula (I) and salts thereof: wherein R1, R2, R3, R4 are defined herein. Compounds of formula (I) and salts thereof have been found to inhibit the binding of the BET family of bromodomain proteins to, for example, acetylated lysine residues and thus may have use in therapy, for example in the treatment of autoimmune and inflammatory diseases, such as rheumatoid arthritis; and cancers.

  式（I）的化合物及其盐：其中R1、R2、R3、R4在此处定义。已发现式（I）的化合物及其盐能够抑制BET家族的溴结构域蛋白与例如乙酰化赖氨酸残基的结合，因此可能在治疗中发挥作用，例如在治疗自身免疫和炎症性疾病（如类风湿性关节炎）和癌症方面。
• [EN] NOVEL 6,7-DIHYDROBENZO[A]QUINOLIZIN-2-ONE DERIVATIVES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION<br/>[FR] NOUVEAUX DÉRIVÉS DE 6,7-DIHYDROBENZO[A]QUINOLIZIN-2-ONE POUR LE TRAITEMENT ET LA PROPHYLAXIE D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016071215A1

  公开（公告）日：2016-05-12

  The invention provides novel compounds having the general formula (I) wherein R1 to R6, W and X are as described herein and their pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

  这项发明提供了具有一般式（I）的新化合物，其中R1至R6、W和X如本文所述，以及它们的药用盐、对映体或二对映体，以及包括这些化合物的组合物和使用这些化合物的方法。
• [EN] ISOINDOLINONE INHIBITORS OF THE MDM2-P53 INTERACTION AND PROCESS FOR MAKING THEM<br/>[FR] INHIBITEURS ISOINDOLINONE DE L'INTERACTION MDM2-P53 ET PROCÉDÉS DE PRÉPARATION DE CES DERNIERS
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2018178691A1

  公开（公告）日：2018-10-04

  The invention relates to processes for preparing isoindolin-1-one derivatives, and in particular processes for preparing (2S,3S)-3-(4-chlorophenyl)-3-[(1R)-1-(4-chlorophenyl)-7-fluoro-5-[(1S)-1-hydroxy-1- (oxan-4-yl)propyl]-1-methoxy-3-oxo-2,3-dihydro-1H-isoindol-2-yl]-2-methylpropanoic acid. The invention also relates to crystalline forms of the compound (2S,3S)-3-(4-chlorophenyl)-3-[(1R)-1-(4- chlorophenyl)-7-fluoro-5-[(1S)-1-hydroxy-1-(oxan-4-yl)propyl]-1-methoxy-3-oxo-2,3-dihydro-1H- isoindol-2-yl]-2-methylpropanoic acid and its salts.

  该发明涉及制备异吲哚啉-1-酮衍生物的方法，特别是制备(2S,3S)-3-(4-氯苯基)-3-[(1R)-1-(4-氯苯基)-7-氟-5-[(1S)-1-羟基-1-(氧戊-4-基)丙基]-1-甲氧基-3-酮基-2,3-二氢-1H-异吲哚-2-基]-2-甲基丙酸的方法。该发明还涉及化合物(2S,3S)-3-(4-氯苯基)-3-[(1R)-1-(4-氯苯基)-7-氟-5-[(1S)-1-羟基-1-(氧戊-4-基)丙基]-1-甲氧基-3-酮基-2,3-二氢-1H-异吲哚-2-基]-2-甲基丙酸及其盐的晶型形式。
• [EN] HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE LA SYNTHÈSE DES LIPIDES ET COMBINAISONS EN CONTENANT
  申请人：3 V BIOSCIENCES INC

  公开号：WO2015095767A1

  公开（公告）日：2015-06-25

  Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.

  提供了杂环调节剂脂质合成以及其药用盐；包括这些化合物的药物组合物；以及通过给予这些化合物和其他治疗剂的组合来治疗脂肪酸合酶途径失调症状的方法。
• Fast Enantio‐ and Chemoselective Arylation of Ketones with Organoboronic Esters Enabled by Nickel/N‐Heterocyclic Carbene Catalysis
  作者：Yuan Cai、Lin‐Xin Ruan、Abdul Rahman、Shi‐Liang Shi

  DOI：10.1002/anie.202015021

  日期：2021.3

  tolerates aryl chlorides, fluorides, ethers, esters, amides, nitriles, and alkyl chlorides. The reaction is applied to late‐stage modifications of various densely functionalized medicinally relevant molecules. Preliminary mechanistic studies suggest that a rare enantioselective η2‐coordinating activation of ketone carbonyls is involved. This cross‐coupling‐like mechanism is expected to enable other challenging

  据报道，一般高效，高度对映和化学选择性的N-杂环卡宾（NHC）/ Ni催化将易于获得的稳定的芳基硼酸酯加到酮中。该协议可提供出乎意料的快速访问权限（通常为10分钟），这些手性叔醇具有特别宽的底物范围和出色的官能团耐受性（76个示例，最高98％ee）。此过程与其他已知的Ni介导的Suzuki-Miyaura偶联正交，因为它可以耐受芳基氯，氟化物，醚，酯，酰胺，腈和烷基氯。该反应适用于各种紧密功能化的医学相关分子的后期修饰。初步机理研究表明，一种罕见的对映选择性η 2涉及酮羰基的配位活化。这种类似交叉耦合的机制有望实现酮类的其他挑战性转化。