4-(4-羟基苯甲酰基)吗啡啉 | 18137-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 4-(4-羟基苯甲酰基)吗啡啉
• 中文别名: 4-(4-吗啉羰基)苯酚
• 英文名称: (4-hydroxyphenyl)(morpholino)methanone
• 英文别名: (4-hydroxyphenyl)-morpholin-4-ylmethanone
• CAS: 18137-25-2
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD00185859
• 分子量: 207.229
• InChiKey: GJHYHTYGGHFYNN-UHFFFAOYSA-N

物化性质

• 沸点：
  422.6±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 储存条件：
  2-8℃，应密封保存，并放置在干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-[(Morpholin-4-yl)carbonyl]phenol
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: 4-[(Morpholin-4-yl)carbonyl]phenol
CAS number: 18137-25-2

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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: C11H13NO3
Molecular weight: 207.2

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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：

  4-(4-羟基苯甲酰基)吗啡啉 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 、 sodium carbonate 、 三乙胺 、 联硼酸频那醇酯 作用下， 以 DMF (N,N-dimethyl-formamide) 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(4-morpholinylcarbonyl)phenyl]-1-benzothiophene-2-carboxamide
  参考文献：
  名称：

  [DE] 2-HETEROARYLCARBONSÄUREAMIDE
  [EN] 2-HETEROARYL CARBOXAMIDES
  [FR] 2-HETEROARYLCARBOXAMIDES

  摘要：

  这项发明涉及新的2-杂环芳基羧酰胺及其用于制备用于治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆能力的药物的用途。其中，R1为1-Aza-bicyclo[2.2.2]oct-3-yl，可能通过氮原子与来自C1-C4-烷基、苄基和氧的基团中的一种取代，A为氧或硫，环B为苯并或吡啶，并且可以通过来自卤素、氰基、甲酰基、三氟甲基、三氟甲氧基、硝基、氨基、C1-C6-烷基和C1-C6-烷氧基的基团取代，E为C≡C、芳基和杂环芳基，其中芳基和杂环芳基可以通过来自卤素、氰基、三氟甲基、三氟甲基、三氟甲氧基、硝基、氨基、C1-C6-烷氧基和C1-C6-烷基的基团取代，以及这些化合物的溶剂化合物、盐或盐的溶剂化合物。

  公开号：

  WO2003104227A1
• 作为产物：
  描述：

  4-acetoxybenzoyl chloride 在 吡啶 、 正丁胺 作用下， 反应 4.0h， 生成 4-(4-羟基苯甲酰基)吗啡啉
  参考文献：
  名称：

  模型实验暗示了LCP合成中的中间体苯醌酮

  摘要：

  由4-羟基苯甲酸（HBA）和共聚单体进行LCP合成涉及在聚合反应后期形成酚阴离子端基。模型反应表明，这些端基可以裂解形成4-氧代-2,5-环己二烯基烯酮OCK（苯醌醌酮中间体），而失去了共振稳定的酚阴离子。用碱将4-（4'-羟基苯甲酰氧基）苯甲酸乙酯形成4-羟基苯甲酸乙酯和聚HBA，而4-（4'-甲氧基苯甲酰氧基）苯甲酸乙酯在相同条件下不反应，表明涉及OCK的E1cB机理为中间的。尝试使用环加成法捕获OCK中间体失败，但成功地将其与仲胺捕获。这些结果使得LCP合成至少部分地通过OCK发生。

  DOI：

  10.1021/ma201105q

文献信息

• A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C: in quest of an industrially viable process
  作者：Masanori Hatsuda、Masahiko Seki

  DOI：10.1016/j.tet.2005.06.061

  日期：2005.10

  heterogeneous Pd/C used as the catalyst. Treatment of aryl bromides 1 with Zn(CN)2 in the presence of Pd/C, Zn, ZnBr2 and PPh3 in DMA provided aryl nitriles 2 involving those carrying sterically demanding electron-rich substituent in good yields and in highly reproducible manner. The activity of Pd/C is highly dependent on the properties of the Pd/C. Oxidic thickshell type catalyst Pd/C D5 was found

  通过芳基溴化物1a的经典Rosenmund-von Braun反应制备芳基腈2a由于高的反应温度（165°C）和缺乏从大量的2a中分离2a的有效程序而导致收率（61％）差。重金属废物（铜盐）。为了解决这些问题，已经开发了通过使用异质Pd / C作为催化剂，通过芳基溴化物的氰化来实际合成多官能芳基腈的方法。在DMA中存在Pd / C，Zn，ZnBr 2和PPh 3的情况下，使用Zn（CN）2处理芳基溴化物1提供了芳基腈2涉及那些以高收率和高度可复制的方式携带空间要求高的富电子取代基的化合物。Pd / C的活性高度依赖于Pd / C的特性。发现氧化厚壳型催化剂Pd / C D5具有最高的速率加速和产率。至少在反应的初始阶段，使用非均质的Pd / C可能会将Pd固定并分散在催化剂的固体载体上，以确保形成单体Pd络合物而不会沉淀成惰性的Pd黑色。使用稍微过量的Zn（CN）2 （0.6当量）和膦配体
• Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides
  作者：José A. Forni、Nenad Micic、Timothy U. Connell、Geethika Weragoda、Anastasios Polyzos

  DOI：10.1002/anie.202006720

  日期：2020.10.12

  visible‐light‐mediated carbonylative amidation of aryl, heteroaryl, and alkyl halides. A tandem catalytic cycle of [Ir(ppy)2(dtb‐bpy)]+ generates a potent iridium photoreductant through a second catalytic cycle in the presence of DIPEA, which productively engages aryl bromides, iodides, and even chlorides as well as primary, secondary, and tertiary alkyl iodides. The versatile in situ generated catalyst is compatible

  我们报告了一种新的可见光介导的芳基，杂芳基和烷基卤化物的羰基酰胺化反应。串联的[Ir（ppy）2（dtb-bpy）] +催化循环在DIPEA存在的情况下通过第二个催化循环产生强力的铱光还原剂，该反应性地使芳基溴化物，碘化物，甚至氯化物与伯，仲和叔烷基碘。这种多功能的原位生成的催化剂可与脂族和芳族胺兼容，具有很高的官能团耐受性，并能使复杂的天然产物后期酰胺化。
• Decarboxylative Hydroxylation of Benzoic Acids
  作者：Wanqi Su、Peng Xu、Tobias Ritter

  DOI：10.1002/anie.202108971

  日期：2021.11.2

  Herein, the first decarboxylative hydroxylation reaction to synthesize phenols from benzoic acids is reported. The method overcomes the challenges associated with conventional decarboxylation of benzoic acids and can be applied even for the late-stage functionalization.

  在此，报道了第一个由苯甲酸合成苯酚的脱羧羟基化反应。该方法克服了与传统苯甲酸脱羧相关的挑战，甚至可以应用于后期功能化。
• Synthesis, biological evaluation and molecular modeling study of 2-amino-3,5-disubstituted-pyrazines as Aurora kinases inhibitors
  作者：Yong-Xin Bo、Rong Xiang、Yu Xu、Shu-Yi Hao、Xing-Rong Wang、Shi-Wu Chen

  DOI：10.1016/j.bmc.2020.115351

  日期：2020.3

  Serine/threonine protein kinases Aurora A, B, and C play essential roles in cell mitosis and cytokinesis, and a number of Aurora kinase inhibitors have been evaluated in the clinic. Herein we report the synthesis and their antiproliferation of 3,5-disubstituted-2-aminopyrazines as kinases inhibitors. Amongst, 4-((3-amino-6- (3,5-dimethylisoxazol-4-yl)pyrazin-2-yl)oxy)-N-(3-chlorophenyl) benzamide (12Aj)

  丝氨酸/苏氨酸蛋白激酶Aurora A，B和C在细胞有丝分裂和胞质分裂中起着至关重要的作用，临床上已经评估了许多Aurora激酶抑制剂。在本文中，我们报道了3,5-二取代-2-氨基吡嗪作为激酶抑制剂的合成及其抗增殖作用。其中，4-（（3-氨基-6-（3,5-二甲基异恶唑-4-基）吡嗪-2-基）氧基）-N-（3-氯苯基）苯甲酰胺（12Aj）对U38表现出最强的抗增殖活性，具有IC50值的HeLa，HepG2和LoVo细胞分别为11.5±3.2、1.34±0.23、7.30±1.56和1.64±0.48μM，以及抑制的Aurora A和B具有IC50值分别为90和152 nM。分子对接研究表明12Aj似乎与Aurora A或Aurora B形成稳定的氢键。12Aj通过调节cyclinB1和cdc2的蛋白质水平，将HeLa细胞周期阻滞在G2 / M期。此外，生物信息学预测还进一步表明，使用Swi
• A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C
  作者：Masanori Hatsuda、Masahiko Seki

  DOI：10.1016/j.tetlet.2005.01.098

  日期：2005.3

  An industrially viable cyanation of aryl bromides with Zn(CN)2 was accomplished in the presence of inexpensive and readily accessible Pd/C, Zn dust, ZnBr2, and PPh3 in DMA to provide functionalized aryl nitriles in moderate to high yields.

  在DMA中存在便宜且易于获得的Pd / C，Zn粉尘，ZnBr 2和PPh 3的情况下，用Zn（CN）2在工业上实现了芳基溴化物的氰化，从而以中等至高收率提供了官能化的芳基腈。