1-二苯甲基氮杂环丁烷-3-酮 | 40320-60-3

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酮
• 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: 1-二苯甲基氮杂环丁烷-3-酮
• 中文别名: 1-(二苯基甲基)-3-氮杂环丁酮；1-二苯甲基-3-氮杂环丁酮；1-二苯基甲基-3-氮杂环丁烷酮；N-二苯甲基氮杂环丁烷-3酮
• 英文名称: N-benzhydryl 3-azetidinone
• 英文别名: N-benzhydrylazetidin-3-one；1-benzhydrylazetidin-3-one
• CAS: 40320-60-3
• 化学式: C₁₆H₁₅NO
• mdl: MFCD00964539
• 分子量: 237.301
• InChiKey: AVUDXLOVIBJFQA-UHFFFAOYSA-N

物化性质

• 熔点：
  75.0 to 79.0 °C
• 沸点：
  350-355℃
• 密度：
  1.182
• 闪点：
  156°(313°F)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于室温且干燥的环境中

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
1-Benzhydrylazetidin-3-one
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
1-Benzhydrylazetidin-3-one
Ingredient name:
CAS number: 40320-60-3

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C16H15NO
Molecular weight: 237.3

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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.

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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

化学性质

1-二苯甲基氮杂环丁烷-3-酮在常温常压下为黄色固体状。在有机合成转化中，其四元环上的酮羰基可以进行Wittig反应生成烯烃类产物，也可以与羟胺进行相应的缩合反应。

应用

1-二苯甲基氮杂环丁烷-3-酮是酮类衍生物，可用作医药中间体。

合成方法

在氩气环境下，将二甲基亚砜（12.45毫升，176毫摩尔）溶解于二氯甲烷（150毫升）中，并冷却至-78℃。在此温度下，逐滴加入草酰氯（8.61毫升，100毫摩尔），搅拌反应30分钟后，再滴加1-苯甲酰基氮杂环丁-3-醇（20克，84毫摩尔）的二氯甲烷（75毫升）溶液。继续在-78℃下搅拌1小时后，慢慢加入三乙胺（58.2毫升，418毫摩尔）。然后将反应混合物缓慢升温至0℃，用饱和氯化铵水溶液（150毫升）淬灭反应，并用二氯甲烷萃取三次。合并的有机层用水和盐水洗涤，无水硫酸钠干燥后浓缩，得到黄色固体粗制1-苯甲基氮杂环丁-3-酮（20.8克，105%）。

反应信息

• 作为反应物：
  描述：

  1-二苯甲基氮杂环丁烷-3-酮 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 、 二甲基亚砜 为溶剂， 反应 2.67h， 生成 5-benzhydryl-1-oxa-5-azaspiro[2.3]hexane
  参考文献：
  名称：

  THERAPEUTIC AGENT FOR RESPIRATORY DISEASE CONTAINING 4-HYDROXYPIPERIDINE DERIVATIVE AS ACTIVE INGREDIENT

  摘要：

  公开号：

  EP1568688B1
• 作为产物：
  描述：

  二苯甲胺盐酸盐 在 sodium hydroxide 作用下， 以 二氯甲烷 、 alkaline aq. solution 、 水 为溶剂， 反应 87.0h， 生成 1-二苯甲基氮杂环丁烷-3-酮
  参考文献：
  名称：

  一种制备3-氮杂环丁烷乙酸的简便方法

  摘要：

  描述了从市售环氧氯丙烷制备新型 3-氮杂环丁烷乙酸的简便途径。

  DOI：

  10.1246/cl.1999.605
• 作为试剂：
  描述：

  4-溴-2,8-二(三氟甲基)喹啉 、 Boc-L-脯氨酸甲酯 在 1-二苯甲基氮杂环丁烷-3-酮 作用下， 以the product (1.32 g, 29%) isolated as a cream solid的产率得到(2S)-(1-tert-butoxycarbonyl-2-pyrrolidinyl) 2,8-bis(trifluoromethyl)quinolin-4-yl methanone
  参考文献：
  名称：

  4-quinolinemethanol derivatives as purine receptor antagonists (II)

  摘要：

  使用公式（I）所定义的化合物，或其药学上可接受的盐或前药，制造用于治疗或预防某种疾病的药物，该疾病中阻断嘌呤受体，特别是腺苷受体，更特别是A2a受体，可能是有益的，例如运动障碍，例如帕金森病或进行性上核性麻痹症，亨廷顿病，多系统萎缩，皮质基底节变性，威尔逊病，哈勒罗德-斯帕茨病，进行性苍白球萎缩，多巴响应性肌张力障碍-帕金森综合症，痉挛性，阿尔茨海默病或其他基底节疾病所导致的运动障碍。

  公开号：

  US06608085B1

文献信息

• Tetrahydrochromenoimidazoles as Potassium-Competitive Acid Blockers (P-CABs): Structure−Activity Relationship of Their Antisecretory Properties and Their Affinity toward the hERG Channel
  作者：Andreas M. Palmer、Vittoria Chiesa、Anja Schmid、Gabriela Münch、Burkhard Grobbel、Peter J. Zimmermann、Christof Brehm、Wilm Buhr、Wolfgang-Alexander Simon、Wolfgang Kromer、Stefan Postius、Jürgen Volz、Dietmar Hess

  DOI：10.1021/jm100040c

  日期：2010.5.13

  Potassium-competitive acid blockers (P-CABs) constitute a new therapeutic option for the treatment of acid-related diseases that are widespread and constitute a significant economical burden. Enantiomerically pure tetrahydrochromenoimidazoles were prepared using the readily available candidate 4 (BYK 405879) as starting material or the Noyori asymmetric reduction of ketones as key reaction. A comprehensive

  钾竞争性酸阻滞剂（P-CAB）构成了治疗与酸有关的疾病的新的治疗选择，这些疾病与疾病相关的疾病广泛且构成重大的经济负担。使用容易获得的候选物4制备对映体纯的四氢色氮咪唑（BYK 405879）作为起始原料或Noyori酮的不对称还原是关键反应。建立了关于5-羧酰胺和8-芳基残基对体外活性，Ghosh Schild大鼠体内酸抑制和对hERG通道的亲和力影响的综合SAR。此外，通过瘘管犬的24 h pH测量，检查了最有希望的目标化合物的抗分泌作用的功效和持续时间，与Ghosh Schild大鼠相比，观察到了明显不同的SAR。鉴定了几种与候选物4具有可比性的四氢色氮咪唑。
• [EN] BRUTON'S TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：PFIZER

  公开号：WO2014068527A1

  公开（公告）日：2014-05-08

  Disclosed herein are compounds that form covalent bonds with Bruton's tyrosine kinase (BTK). Methods for the preparation of the compounds are disclosed. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the BTK inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions. (Formula I)

  本文披露了一种与Bruton's酪氨酸激酶（BTK）形成共价键的化合物。公开了制备这些化合物的方法。还披露了包括这些化合物的药物组合物。公开了使用BTK抑制剂的方法，单独或与其他治疗剂联合治疗自身免疫疾病或症状、异源免疫疾病或症状、癌症，包括淋巴瘤，以及炎症性疾病或症状的方法。 (化学式I)
• TAU-PROTEIN TARGETING PROTACS AND ASSOCIATED METHODS OF USE
  申请人：Arvinas, Inc.

  公开号：US20180125821A1

  公开（公告）日：2018-05-10

  The present disclosure relates to bifunctional compounds, which find utility as modulators of tau protein. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a VHL or cereblon ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds tau protein, such that tau protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of tau. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of tau protein. Diseases or disorders that result from aggregation or accumulation of tau protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为tau蛋白的调节剂具有实用性。具体而言，本公开涉及含有一端结合到E3泛素连接酶的VHL或cereblon配体，另一端结合到tau蛋白的双功能化合物，使得tau蛋白与泛素连接酶靠近，以实现tau蛋白的降解（和抑制）。本公开展示了与tau蛋白降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由tau蛋白聚集或积累导致的疾病或紊乱。
• [EN] CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE LA CÉRAMIDE GALACTOSYLTRANSFÉRASE POUR LE TRAITEMENT DE MALADIES
  申请人：BIOMARIN PHARM INC

  公开号：WO2017214505A1

  公开（公告）日：2017-12-14

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物、以及使用这种化合物治疗或预防与酶神经鞘糖脂转移酶（CGT）相关的疾病或紊乱的方法，例如溶酶体贮积症。溶酶体贮积症的例子包括 Krabbe 病和白质变性白血病。
• Substituted triazole derivatives as oxytocin antagonists
  申请人：Brown Daniel Alan

  公开号：US20060160786A1

  公开（公告）日：2006-07-20

  The present invention relates to substituted triazoles of formula (I), uses thereof, processes for the preparation thereof and compositions containing said compounds. These inhibitors have utility in a variety of therapeutic areas including sexual dysfunction.

  本发明涉及公式（I）的取代三唑化合物，其用途，制备方法以及含有该化合物的组合物。这些抑制剂在包括性功能障碍在内的各种治疗领域具有用途。