2,3,4,5-四氢苯并[c]氮杂-1-酮 | 6729-50-6

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 2,3,4,5-四氢苯并[c]氮杂-1-酮
• 中文别名: 2,3,4,5-四氢-1H-2-苯并氮杂卓-1-酮
• 英文名称: 2,3,4,5-tetrahydro-1H-2-benzazepin-1-one
• 英文别名: 2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one；2,3,4,5-tetrahydro-1H-2-benzazepine-1-one；2,3,4,5-tetrahydro-benzo[c]azepin-1-one；2,3,4,5-tetrahydro-2-benzazepin-1-one
• CAS: 6729-50-6
• 化学式: C₁₀H₁₁NO
• mdl: MFCD04114867
• 分子量: 161.203
• InChiKey: WWQPGNZHJFFKRW-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  392.5±12.0 °C(Predicted)
• 密度：
  1.100

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,3,4,5-Tetrahydro-benzo[c]azepin-1-one
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H411: Toxic to aquatic life with long lasting effects
P273: Avoid release to the environment

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Section 3. Composition/information on ingredients.
Ingredient name: 2,3,4,5-Tetrahydro-benzo[c]azepin-1-one
CAS number: 6729-50-6

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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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H11NO
Molecular weight: 161.2

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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：

  2,3,4,5-四氢苯并[c]氮杂-1-酮 在 氯磺酸 作用下， 生成 1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-8-sulfonyl chloride
  参考文献：
  名称：

  作为乙型肝炎病毒衣壳组装效应子的氨磺酰苯甲酰胺衍生物的合成

  摘要：

  报道了作为 HBV 衣壳组装效应物的新型氨磺酰苯甲酰胺系列的合成。该结构分为五个部分，作为我们先导化合物优化的一部分，这些部分被独立修改。所有合成的化合物均在人肝细胞、淋巴细胞和其他细胞中评估其抗乙肝病毒活性和毒性。此外，我们还在基于 HBeAg 报告细胞的测定中评估了它们对 HBV cccDNA 形成的影响。在报道的 27 种化合物中，几种类似物表现出亚微摩尔活性并显着减少 HBeAg 分泌。在负染色电子显微镜下研究了所选化合物破坏 HBV 衣壳形成的能力。将结构建模为最近在 HBV 衣壳蛋白中发现的类似分子的结合位点，以合理化该化合物家族的结构-活性关系。

  DOI：

  10.1016/j.ejmech.2017.06.062
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 盐酸 、 sodium azide 作用下， 以 水 为溶剂， 反应 16.0h， 以48%的产率得到2,3,4,5-四氢苯并[c]氮杂-1-酮
  参考文献：
  名称：

  铱催化的晚期Strecker反应用于后期酰胺和内酰胺氰化反应

  摘要：

  报道了一种新的铱催化的还原斯特雷克反应，该反应可从多种（杂）芳族和脂肪族叔酰胺以及N-烷基内酰胺直接有效地形成α-氨基腈产物。该协议利用IrCl（CO）[P（C 6 H 5）3 ] 2利用酰胺和内酰胺官能团进行轻度和高度化学选择性还原（Vaska's complex）（Vaska's complex）在存在还原剂的四甲基二硅氧烷的情况下，直接生成可通过TMSCN（TMS =三甲基甲硅烷基）处理而被氰化物取代的半胱氨酸类物质。该方案操作简单，适用范围广，有效（最高收率99％），已成功应用于含酰胺和内酰胺的药物以及天然生物碱的后期功能化以及与二肽和三肽中脯氨酸残基的N原子连接的羰基碳原子的选择性氰化。

  DOI：

  10.1002/anie.201612367

文献信息

• Copper(I)-Catalyzed Enantioselective Incorporation of Ketones to Cyclic Hemiaminals for the Synthesis of Versatile Alkaloid Precursors
  作者：Shi-Liang Shi、Xiao-Feng Wei、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/ja308872z

  日期：2012.10.17

  A general catalytic enantioselective method that can produce five-, six-, and seven-membered N-heterocycles possessing various ketone moieties starting from stable and easily available cyclic hemiaminals and ketones was developed. The method involves three successive steps in one pot (aldol addition, dehydration, and enantioselective intramolecular aza-Michael reaction), all of which are promoted by

  开发了一种通用的催化对映选择性方法，该方法可以从稳定且易于获得的环状半胺醛和酮开始生产具有各种酮部分的五元、六元和七元 N-杂环。该方法包括三个连续步骤（醛醇加成、脱水和对映选择性分子内氮杂-迈克尔反应），所有这些都由手性铜（I）-共轭 Brønsted 碱催化剂促进。该方法可用于快速获取用于合成药物铅生物碱的通用手性构件。
• Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions
  作者：Kengo Hyodo、Genna Hasegawa、Naoki Oishi、Kazuma Kuroda、Kingo Uchida

  DOI：10.1021/acs.joc.8b01810

  日期：2018.11.2

  The Brønsted acid-catalyzed synthesis of secondary amides from ketones under mild conditions is described via transoximation and Beckmann rearrangement using O-protected oximes as more stable equivalents of explosive O-protected hydroxylamines. This methodology could be applied to highly rearrangement-selective amide synthesis from α-branched alkyl aryl ketones and performed on a 1-g scale. The presence

  描述了在温和条件下布朗斯台德酸催化的酮类合成仲酰胺的方法，是通过氧肟化反应和贝克曼重排反应，使用O保护的肟作为更稳定的等价炸药O保护的羟胺。该方法可用于由α-支链烷基芳基酮合成的高度重排选择性酰胺，并以1 g规模进行。水的存在对于该反应是必不可少的，并且其作用已通过同位素标记实验得以阐明。
• Synthesis, 3D-QSAR, and Structural Modeling of Benzolactam Derivatives with Binding Affinity for the D2 and D3 Receptors
  作者：Laura López、Jana Selent、Raquel Ortega、Christian F. Masaguer、Eduardo Domínguez、Filipe Areias、José Brea、María Isabel Loza、Ferran Sanz、Manuel Pastor

  DOI：10.1002/cmdc.201000101

  日期：——

  series of 37 benzolactam derivatives were synthesized, and their respective affinities for the dopamine D2 and D3 receptors evaluated. The relationships between structures and binding affinities were investigated using both ligand‐based (3D‐QSAR) and receptor‐based methods. The results revealed the importance of diverse structural features in explaining the differences in the observed affinities, such as

  合成了一系列37种苯并内酰胺衍生物，并评估了它们各自对多巴胺D 2和D 3受体的亲和力。使用基于配体的方法（3D-QSAR）和基于受体的方法研究了结构与结合亲和力之间的关系。结果表明，在解释所观察到的亲和力方面的差异（例如苯并内酰胺羰基氧的位置或化合物的总长度）时，各种结构特征的重要性。对于D 2和D 3，此类配体性质的最佳值略有不同即使结合位点表现出非常高的同源性，受体也是如此。我们解释通过氢键网络的在d中存在这些差异2受体这是在d缺席3受体并限制了结合口袋的尺寸，造成在螺旋7个残基变得不那么访问。这些结果对设计更有效和选择性更高的苯并内酰胺衍生物的意义进行了介绍和讨论。
• Cobalt-catalysed C–H methylation for late-stage drug diversification
  作者：Stig D. Friis、Magnus J. Johansson、Lutz Ackermann

  DOI：10.1038/s41557-020-0475-7

  日期：2020.6

  despite its significance, accessing such analogues via derivatization at a late stage remains a pivotal challenge. In an effort to mitigate this major limitation, we here present a strategy for the cobalt-catalysed late-stage C–H methylation of structurally complex drug molecules. Enabling broad applicability, the transformation relies on a boron-based methyl source and takes advantage of inherently present

  神奇的甲基效应在药物化学中广为人知，但尽管意义重大，但在后期通过衍生化获得此类类似物仍然是一项关键挑战。为了减轻这一主要限制，我们在此提出了一种策略，用于对结构复杂的药物分子进行钴催化的后期C–H甲基化。这种转化具有广泛的适用性，它依赖于基于硼的甲基源，并利用固有存在的官能团来引导C–H活化。确定在不同功能类别下观察到的相对反应性，并在各种反应条件下测试转化对一组常见功能基序的敏感性。无需预功能化或后脱保护，市场上出售的各种药物分子和天然产物可以以可预测的方式甲基化。随后的理化和生物学测试证实了这种看似微小的结构变化可影响重要药物特性的程度。
• ARYL AND HETEROARYL FUSED LACTAMS
  申请人：PFIZER INC.

  公开号：US20140179667A1

  公开（公告）日：2014-06-26

  This invention relates to compounds of general formula (I) in which R 1 , R 2 , U, V, L, M, R 5 , m, X, Y and Z are as defined herein, and the pharmaceutically acceptable salts thereof, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer.

  本发明涉及具有通用公式（I）的化合物，其中R1，R2，U，V，L，M，R5，m，X，Y和Z定义如本文中所述，以及药用可接受的盐，包含此类化合物和盐的药物组合物，以及使用此类化合物、盐和组合物治疗异常细胞生长，包括癌症的方法。