3-乙酰基苯硼酸频那醇酯 | 214360-49-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙酰基苯硼酸频那醇酯
• 中文别名: 3-乙酰基苯硼酸频哪醇酯；1-(3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)苯基)乙酮
• 英文名称: 1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone
• 英文别名: 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one；1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone；1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone
• CAS: 214360-49-3
• 化学式: C₁₄H₁₉BO₃
• mdl: MFCD05863923
• 分子量: 246.114
• InChiKey: CMMASGVZWZQOEY-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52°C
• 沸点：
  362.5±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Acetylphenylboronic acid, pinacol ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Acetylphenylboronic acid, pinacol ester
CAS number: 214360-49-3

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C14H19BO3
Molecular weight: 246.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-乙酰基苯硼酸频那醇酯 在 4-hydroxyacetophenone monooxygenase from Pseudomonas fluorescens 、 phosphite dehydrogenase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 二甲基亚砜 为溶剂， 生成 间苯二酚
  参考文献：
  名称：

  拜耳-维利格单加氧酶催化的有机硼化合物的选择性氧化

  摘要：

  通过测试各种含硼芳族和乙烯基化合物的化学和对映选择性氧化，探索了拜耳－威利格单加氧酶（BVMOs）在有机硼化学中的适用性。本研究使用了几种BVMO，即：苯丙酮单加氧酶（PAMO），M446G PAMO突变体，4-羟基苯乙酮单加氧酶（HAPMO）和环己酮单加氧酶（CHMO）。化学选择性的程度取决于所使用的BVMO的类型，在这种类型中，生物催化剂更喜欢硼碳氧化而不是Baeyer-Villiger氧化或环氧化。有趣的是，发现PAMO可用于以良好的对映选择性对含硼化合物进行动力学拆分。

  DOI：

  10.1002/adsc.201100029
• 作为产物：
  描述：

  3-羟基苯乙酮 在 potassium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.0h， 生成 3-乙酰基苯硼酸频那醇酯
  参考文献：
  名称：

  钯催化的甲磺酸烷基酯和甲苯磺酸酯的硼化反应及其在一锅顺序铃木-宫浦联芳的合成中的应用

  摘要：

  一锅之巅！描述了芳基甲苯磺酸盐和甲磺酸盐的第一个钯催化的硼化反应。反应条件温和，并具有出色的官能团相容性（例如，R = CN，CHO，COOMe，C（O）R，NH 2或NH-吲哚；请参见方案）。Pd / MeO-CM-phos可在不对称联芳烃的制备中进行一锅法依次反应。

  DOI：

  10.1002/chem.201100361

文献信息

• Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross-Coupling
  作者：Chung-Yang (Dennis) Huang、Abigail G. Doyle

  DOI：10.1021/jacs.5b02503

  日期：2015.5.6

  A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination. This ligand

  已开发出镍催化的 Negishi 与 1,1-二取代苯乙烯基氮丙啶的交叉偶联。该方法通过提供季碳的具有挑战性的还原消除来提供有价值的 β-取代苯乙胺。一种新型缺电子烯烃配体 Fro-DO 被证明对于通过 β-H 消除实现 CC 键形成的高速率和化学选择性至关重要。该配体易于获取、稳定，并为反应发现和优化提供了模块化框架。我们预计这些属性，再加上配体赋予金属不同的电子特性，将支持使用既定配体以前不可能实现的新转化的发明。
• [EN] CONDENSED IMIDAZOLE DERIVATIVES SUBSTITUTED BY TERTIARY HYDROXY GROUPS AS PI3K-GAMMA INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZOLE CONDENSÉS, SUBSTITUÉS PAR DES GROUPES HYDROXY TERTIAIRES, UTILISÉS COMME INHIBITEURS DE PI3K-GAMMA
  申请人：INCYTE CORP

  公开号：WO2019079469A1

  公开（公告）日：2019-04-25

  This application relates to compounds of Formula (I): or pharmaceutically acceptable salts thereof, which are inhibitors of PI3K-y which are useful for the treatment of disorders such as autoimmune diseases, cancer, cardiovascular diseases, and neurodegenerative diseases.

  这种应用涉及到式(I)的化合物或其药用可接受的盐，这些化合物是PI3K-y的抑制剂，对于治疗自身免疫疾病、癌症、心血管疾病和神经退行性疾病等疾病是有用的。
• Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes
  作者：Astrid M. Olivares、Daniel J. Weix

  DOI：10.1021/jacs.7b13601

  日期：2018.2.21

  synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5'-bis(trifluoromethyl)-2,2'-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult

  首次报道了由溴乙烯与三氟甲磺酸乙烯酯偶联合成高度取代的1,3-二烯。该偶联反应由 (5,5'-双(三氟甲基)-2,2'-联吡啶)NiBr2 和 (1,3-双(二苯基膦)丙烷)PdCl2 在锌还原剂存在下的组合催化。该方法提供了四取代和五取代的1,3-二烯，否则这些1,3-二烯很难获得，并且可以耐受富电子和贫电子取代基、杂环、芳基溴和频哪醇硼酸酯。从机理上讲，该反应似乎是通过镍和钯中心之间异常的锌介导的乙烯基转移来进行的。
• Direct Conversion of Arylamines to Pinacol Boronates: A Metal-Free Borylation Process
  作者：Fanyang Mo、Yubo Jiang、Di Qiu、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.200905824

  日期：2010.3.1

  Leave the metal out: Arylboronates are produced in moderate to good yields by direct borylation of readily available aryl amines (see scheme). The reaction can be carried out under air at room temperature and transition‐metal catalysis is not required. The boronate products can be used without purification in Suzuki–Miyaura cross‐coupling reactions.

  排除金属：芳基硼酸酯是通过将容易获得的芳基胺直接硼化而以中等至良好的产率生产的（参见方案）。该反应可在室温下于空气中进行，不需要过渡金属催化。硼酸酯产物无需纯化即可用于Suzuki-Miyaura交叉偶联反应。
• [EN] OLEFIN SUBSTITUTED OXINDOLES HAVING AMPK ACTIVITY<br/>[FR] OXINDOLES SUBSTITUÉS PAR OLÉFINE AYANT UNE ACTIVITÉ SUR AMPK
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014202528A1

  公开（公告）日：2014-12-24

  The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及具有有价值的药理特性的式(I)化合物，特别是AMPK激活剂，因此在治疗某些可以通过激活该受体预防或治疗的疾病方面具有用处。这些化合物适用于治疗和预防可以受该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。