2-(E-3-甲氧基-3-氧代-1-丙烯-1-基)苯基硼酸 | 372193-68-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-(E-3-甲氧基-3-氧代-1-丙烯-1-基)苯基硼酸
• 中文别名: 2-(反式-3-甲氧基-3-羰基-1-丙烯-1-基)苯硼酸；[2-(E-3-甲氧基-3-氧代-1-丙烯-1-基)苯基]硼酸
• 英文名称: [2-((E)-3-methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid
• 英文别名: trans-2-(2-methoxycarbonylvinyl)benzeneboronic acid；2-(3-methoxy-3-oxoprop-1-enyl)phenylboronic acid；[2-(E-3-Methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid；[2-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl]boronic acid
• CAS: 372193-68-5
• 化学式: C₁₀H₁₁BO₄
• 分子量: 206.006
• InChiKey: WUEIYHVPDHJGLC-VOTSOKGWSA-N

物化性质

• 熔点：
  180-186°C
• 沸点：
  400.3±47.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P210,P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-(E-3-Methoxy-3-oxo-1-propen-1-yl)phenylboronic acid
Product Name:
Synonyms: Methyl 2-boronocinnamate

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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.
2-(E-3-Methoxy-3-oxo-1-propen-1-yl)phenylboronic acid
Ingredient name:
CAS number: 372193-68-5

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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.

---

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, refrigerated.

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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: C10H11BO4
Molecular weight: 206.0

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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.

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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-(E-3-甲氧基-3-氧代-1-丙烯-1-基)苯基硼酸 、 2-morpholin-4-yl-4-oxo-4H-chromen-8-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以38%的产率得到3-[2-(2-morpholin-4-yl-4-oxo-4H-chromen-8-yl)phenyl]acrylic acid methyl ester
  参考文献：
  名称：

  Discovery of Potent Chromen-4-one Inhibitors of the DNA-Dependent Protein Kinase (DNA-PK) Using a Small-Molecule Library Approach

  摘要：

  Structure-activity relationships for inhibition of DNA-dependent protein kinase (DNA-PK) have been defined for substituted chromen-4-ones. For the 2-amino-substituted benzo[h]chromen-4-ones, a morpholine substituent at this position was essential for activity. Small libraries of 6- and 7-alkoxy-substituted chromen-4-ones showed that a number of 7-alkoxysubstituted chromenones displayed improved activity. Focused libraries incorporating 6-, 7-, and 8-aryl and heteroaryl substituents were prepared. In these cases, 6- and 7-substitution was disfavored, whereas 8-substitution was largely tolerated. Surprisingly, two compounds, 2-N-morpholino-8-dibenzofuranyl-chromen-4-one (NU7427, 32{38}) and the 2-N-morpholino-8-dibenzothiophenyl-chromen-4-one (NU7441, 32{26}) were excellent inhibitors (IC50 vs DNAPK = 40 and 13 nM, respectively). The ring-saturated analogue 2-N-morpholino-8-(6',7',8',9'-tetrahydrodibenzothiophene)chromen-4-one, 36, retained potent activity (IC50 vs DNA-PK = 23 nM). The dibenzothiophene 32{38} sensitized HeLa cells to ionizing radiation in vitro, with dose modification factors of 2.5 at 10% survival being observed at 0.5 mu M. The cytotoxicity of the topoisomerase II inhibitor etoposide was also potentiated.

  DOI：

  10.1021/jm050444b
• 作为产物：
  描述：

  methyl (2E)-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acrylate 在 盐酸 、 sodium periodate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 2-(E-3-甲氧基-3-氧代-1-丙烯-1-基)苯基硼酸
  参考文献：
  名称：

  Bromo-Boronolactonization of Olefins¹

  摘要：

  Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/ H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.

  DOI：

  10.1021/jo015838z

文献信息

• Hydrogen‐Bonding Organocatalysis Enabled Photocatalytic Intramolecular [2+2]‐Cycloaddition Reaction
  作者：Stefania Perulli、Om Desai、Sandra Ardevines、Mustafa Uygur、Samuel Delgado‐Hernández、Olga García Mancheño

  DOI：10.1002/adsc.202301217

  日期：2024.2.20

  enantioselectivity have been neglected. Scheme 1 Open in figure viewerPowerPoint Hydrogen-bonding promoted intramolecular photocatalyzed cyclizations by LUMO-lowering: a) previous [2+2] photochemical strategies, b) photoredox catalyzed bisenone reaction, and c) this approach on HB-enabled intramolecular [2+2]-cycloaddition of one-site binding carbonyl substrates. Inspired by the mentioned breakthroughs and

  有机催化活化1与光催化2的融合最近已成为一种强大的工具，3可以在具有挑战性的光介导过程中实现新的反应性和立体控制。4除了涉及 MacMillan、 4 Rueping、5和 Rovis等团队的共价活化的开创性工作之外， 6路易斯酸7和布朗斯台德酸催化8也得到了有效的应用。此外，方向性较小的非共价氢键（HB）9相互作用近年来也受到了广泛关注。特别是，通过降低 LUMO 来激活羰基底物，促进光氧化还原单电子转移 (SET) 或能量转移 (EnT) 过程，代表了一种有效的新兴策略。 虽然分子间 [2+2]-环加成得到了广泛研究，并构成了评估新型光催化 EnT 系统的基准反应，但10 种分子内策略的探索较少。在此背景下，Bach 及其同事利用烯酮氢键 LUMO 降低现象开发了一些不对称能量转移 [2+2]-光环加成方法。11, 12 2009 年，他们报道了一种噻吨酮三重态敏化剂，其带有模板 HB
• 2,6-Disubstituted pyran-4-one and thiopyran-4-one inhibitors of DNA-Dependent protein kinase (DNA-PK)
  作者：Jonathan J. Hollick、Bernard T. Golding、Ian R. Hardcastle、Niall Martin、Caroline Richardson、Laurent J.M. Rigoreau、Graeme C.M. Smith、Roger J. Griffin

  DOI：10.1016/s0960-894x(03)00652-8

  日期：2003.9

  6-Aryl-2-morpholin-4-yl-4H-pyran-4-ones and 6-aryl-2-morpholin-4-yl-4H-thiopyran-4-ones were synthesised and evaluated as potential inhibitors of the DNA repair enzyme DNA-dependent protein kinase (DNA-PK). Several compounds in each series exhibited superior activity to the chromenone LY294002, and were of comparable potency to the benzochromenone NU7026 (IC50=0.23 muM). Importantly, members of both structural classes were found to be selective inhibitors of DNA-PK over related phosphatidylinositol 3-kinase-related kinase (PIKK) family members. A multiple-parallel synthesis approach, employing Suzuki cross-coupling methodology, was utilised to prepare libraries of thiopyran-4-ones with a range of aromatic groups at the 3'- and 4'-positions on the thiopyran-4-one 6-aryl ring. Screening of the libraries resulted in the identification of 6-aryl-2-morpholin-4-yl-4H-thiopyran-4-ones bearing naphthyl or benzo[b]thienyl substituents at the 4'-position, as potent DNA-PK inhibitors with IC50 values in the 0.2-0.4 muM range. (C) 2003 Elsevier Ltd. All rights reserved.
• Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase
  作者：Jonathan J. Hollick、Laurent J. M. Rigoreau、Celine Cano-Soumillac、Xiaoling Cockcroft、Nicola J. Curtin、Mark Frigerio、Bernard T. Golding、Sophie Guiard、Ian R. Hardcastle、Ian Hickson、Marc G. Hummersone、Keith A. Menear、Niall M. B. Martin、Ian Matthews、David R. Newell、Rachel Ord、Caroline J. Richardson、Graeme C. M. Smith、Roger J. Griffin

  DOI：10.1021/jm061121y

  日期：2007.4.1

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.
• Discovery of Potent Chromen-4-one Inhibitors of the DNA-Dependent Protein Kinase (DNA-PK) Using a Small-Molecule Library Approach
  作者：Ian R. Hardcastle、Xiaoling Cockcroft、Nicola J. Curtin、Marine Desage El-Murr、Justin J. J. Leahy、Martin Stockley、Bernard T. Golding、Laurent Rigoreau、Caroline Richardson、Graeme C. M. Smith、Roger J. Griffin

  DOI：10.1021/jm050444b

  日期：2005.12.1

  Structure-activity relationships for inhibition of DNA-dependent protein kinase (DNA-PK) have been defined for substituted chromen-4-ones. For the 2-amino-substituted benzo[h]chromen-4-ones, a morpholine substituent at this position was essential for activity. Small libraries of 6- and 7-alkoxy-substituted chromen-4-ones showed that a number of 7-alkoxysubstituted chromenones displayed improved activity. Focused libraries incorporating 6-, 7-, and 8-aryl and heteroaryl substituents were prepared. In these cases, 6- and 7-substitution was disfavored, whereas 8-substitution was largely tolerated. Surprisingly, two compounds, 2-N-morpholino-8-dibenzofuranyl-chromen-4-one (NU7427, 3238}) and the 2-N-morpholino-8-dibenzothiophenyl-chromen-4-one (NU7441, 3226}) were excellent inhibitors (IC50 vs DNAPK = 40 and 13 nM, respectively). The ring-saturated analogue 2-N-morpholino-8-(6',7',8',9'-tetrahydrodibenzothiophene)chromen-4-one, 36, retained potent activity (IC50 vs DNA-PK = 23 nM). The dibenzothiophene 3238} sensitized HeLa cells to ionizing radiation in vitro, with dose modification factors of 2.5 at 10% survival being observed at 0.5 mu M. The cytotoxicity of the topoisomerase II inhibitor etoposide was also potentiated.
• Bromo-Boronolactonization of Olefins¹
  作者：J. R. Falck、Muralidhar Bondlela、Sylesh K. Venkataraman、Dale Srinivas

  DOI：10.1021/jo015838z

  日期：2001.10.1

  Exposure of a variety of mono- and disubstituted ortho-alkenylarylboronic acids to NBS in THF/ H2O under neutral conditions affords bromo-boronolactones, in some instances, with exceptional regiocontrol. The adducts, analogous to those formed by carboxylic acids, are shown to be useful synthetic intermediates.