3-(N,N-二乙基甲酰氨)苯基硼酸 | 237413-05-7

• 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: 3-(N,N-二乙基甲酰氨)苯基硼酸
• 中文别名: 3-(N,N-二乙基氨甲酰基)苯硼酸；3-(二乙基氨甲酰基)苯硼酸
• 英文名称: 3-(diethylamino)carbonylphenylboronic acid
• 英文别名: 3-(N,N-diethylaminocarbonyl)phenylboronic acid；3-(diethylcarbamoyl)phenylboronic acid；[3-(diethylcarbamoyl)phenyl]boronic acid
• CAS: 237413-05-7
• 化学式: C₁₁H₁₆BNO₃
• mdl: MFCD04115684
• 分子量: 221.064
• InChiKey: DDHUSSNOKNYLAI-UHFFFAOYSA-N

物化性质

• 熔点：
  132-136°C
• 沸点：
  436.4±47.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(N,N-Diethylaminocarbonyl)phenylboronic acid
Product Name:
Synonyms: N,N-Diethyl 3-boronobenzamide

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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.
3-(N,N-Diethylaminocarbonyl)phenylboronic acid
Ingredient name:
CAS number: 237413-05-7

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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: C11H16BNO3
Molecular weight: 221.1

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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：

  tert-butyl 4-(trifluoromethylsulfonyloxy)spiro[chromene-2,4'-piperidine]-1'-carboxylate 、 3-(N,N-二乙基甲酰氨)苯基硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 tert-butyl 4-(3-(diethylcarbamoyl)phenyl)spiro[chromene-2,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Potent, Orally Bioavailable Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of N,N-Diethyl-4-(5-hydroxyspiro[chromene-2,4′-piperidine]-4-yl)benzamide (ADL5859)

  摘要：

  Selective 6 opioid receptor agonists are promising potential therapeutic agents for the treatment of various types of pain conditions. A spirocyclic derivative was identified as a promising hit through screening. Subsequent lead optimization identified compound 20 (ADL5859) as a potent, selective, and orally bioavailable 6 agonist. Compound 20 was selected as a clinical candidate for the treatment of pain.

  DOI：

  10.1021/jm8008986
• 作为产物：
  描述：

  3-羧基苯硼酸 、 二乙胺 在 N,N-diethanolaminomethyl polystyrene 、 水 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.02h， 以77%的产率得到3-(N,N-二乙基甲酰氨)苯基硼酸
  参考文献：
  名称：

  通用固相方法用于硼酸的固定化，衍生化和树脂到树脂的转移反应。

  摘要：

  含硼酸的分子广泛用于生物学，医学和合成领域。然而，这些化合物往往难以通过溶液相方法处理。在此，该问题通过用于官能化硼酸的衍生化的第一种通用固相方法的开发来解决。该方法基于使用二乙醇胺树脂锚，该锚通过避免在酯化过程中彻底去除水的需要而促进了硼酸的固定。通过在室温下在无水溶剂中简单搅拌，可以在数分钟内将多种硼酸固定在N，N-二乙醇氨基甲基聚苯乙烯（DEAM-PS，1）上。通过（1）DEAM-PS负载的对甲苯基硼酸的（1）NMR分析显示了形成具有假定的NB配位的双环二乙醇胺硼酸酯的证据。通过紫外光谱研究了DEAM-PS树脂对相同型号硼酸的水解裂解。水解和附着显示在快速达到的平衡下发生，并且需要大量过量的水（> 32当量）以实现从DEAM-PS实际定量释放硼酸。尽管它们对水和醇具有相对的敏感性，但可以用甲酰基，溴甲基，羧基或氨基官能化的DEAM-PS结合的芳基硼酸以良好或极高的收率转化成各种胺，酰

  DOI：

  10.1021/jo0106501

文献信息

• Fluorous Tagged <i>N</i>-Hydroxy Phthalimide for the Parallel Synthesis of <i>O</i>-Aryloxyamines
  作者：Florence S. Gaucher-Wieczorek、Ludovic T. Maillard、Bernard Badet、Philippe Durand

  DOI：10.1021/cc100098v

  日期：2010.9.13

  The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi’s method. A library of O-aryloxyamines

  在药物化学和基于片段的方法领域中，O-芳氧基胺的平行合成仍未满足。为了填补这一空白，采用了一种溶液阶段两步法，该方法基于（1）铜催化的芳基硼酸与带有氟标记的N-羟基邻苯二甲酰亚胺的交叉偶联，以及（2）使用Taguchi方法设计并优化了负载型氨解反应。以高产率，高纯度和多样性合成了O-芳氧基胺的文库。
• Discovery of Arylsulfonamides as Dual Orexin Receptor Agonists
  作者：Dehui Zhang、David A. Perrey、Ann M. Decker、Tiffany L. Langston、Vijayakumar Mavanji、Danni L. Harris、Catherine M. Kotz、Yanan Zhang

  DOI：10.1021/acs.jmedchem.1c00841

  日期：2021.6.24

  Loss of orexin-producing neurons results in narcolepsy with cataplexy, and orexin agonists have been shown to increase wakefulness and alleviate narcolepsy symptoms in animal models. Several OX2R agonists have been reported but with little or no activity at OX1R. We conducted structure–activity relationship studies on the OX2R agonist YNT-185 (2) and discovered dual agonists such as RTOXA-43 (40) with

  产生食欲素的神经元的丧失会导致发作性睡病并猝倒，而食欲素激动剂已被证明可以在动物模型中提高清醒度并减轻发作性睡病症状。已报道了几种 OX2R 激动剂，但对 OX1R 的活性很少或没有。我们对 OX2R 激动剂 YNT-185 ( 2 ) 进行了结构-活性关系研究，发现了双重激动剂，例如 RTOXA-43 ( 40 )，对 OX2R 和 OX1R 的 EC 50均为 24 nM。基于激动剂结合的 OX2R 低温电子显微镜结构的计算模型研究表明， 40结合在同一结合袋中，并且40的吡啶甲基与 OX1R 的相互作用可能有助于其高 OX1R 效力。腹腔注射40可以增加 12 个月大小鼠的清醒时间，减少睡眠时间，并增加睡眠/觉醒巩固。这项工作提供了一种有前途的双重小分子激动剂，并支持食欲素激动剂的开发，作为治疗嗜睡症等食欲素缺乏症的潜在治疗方法。
• ARYL AND ARYLALKYLENYL SUBSTITUTED THIAZOLOQUINOLINES AND THIAZOLONAPHTHYRIDINES
  申请人：Prince B. Ryan

  公开号：US20070259907A1

  公开（公告）日：2007-11-08

  Thiazoloquinoline and thiazolonaphthyridine compounds having an aryl or arylalkylenyl substituent at the 6-, 7-, 8-, or 9-position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明公开了在6、7、8或9位具有芳基或芳基烷基取代基的噻唑喹啉和噻唑萘啶化合物、含有该化合物的制药组合物、中间体以及这些化合物作为免疫调节剂、用于调节动物细胞因子生物合成以及治疗包括病毒和肿瘤疾病的方法。
• CATECHOL O-METHYLTRANSFERASE ACTIVITY INHIBITING COMPOUNDS
  申请人：Orion Corporation

  公开号：US20150218124A1

  公开（公告）日：2015-08-06

  Compounds of formula (I), wherein R 1 is as defined in the claims, exhibit COMT enzyme inhibiting activity and are thus useful as COMT inhibitors. Methods of treatment and pharmaceutical dosage forms are also disclosed.

  式(I)的化合物，其中R1如权利要求所定义，表现出COMT酶抑制活性，因此可用作COMT抑制剂。还公开了治疗方法和制药剂量形式。
• 4,7-Diaryl indole-based fluorescent chemosensor for iodide ions
  作者：Krishnaswamy R. Rathikrishnan、Vellore K. Indirapriyadharshini、Seeram Ramakrishna、Rajendiran Murugan

  DOI：10.1016/j.tet.2011.04.039

  日期：2011.6

  Simple and selective indole based fluorescent sensors for iodide anions are reported. A series of 4,7-diaryl indole derivatives (DAIs) are designed and synthesized using Suzuki coupling. These DAIs shows significant changes in UV-vis and fluorescent intensity only with addition of iodides and not with other anions. The ability of these DAIS to function as selective iodide chemosensor is reported. (C) 2011 Elsevier Ltd. All rights reserved.