7-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-3,4-二氢-2H-苯并[b][1,4]噁嗪 | 1361110-64-6

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 7-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-3,4-二氢-2H-苯并[b][1,4]噁嗪
• 中文别名: 3,4-二氢-7-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)-2H-1,4-苯并恶嗪
• 英文名称: 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine
• 英文别名: 7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine；7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-1,4-benzoxazine
• CAS: 1361110-64-6
• 化学式: C₁₄H₂₀BNO₃
• 分子量: 261.129
• InChiKey: AUGHRUKXHXNOCW-UHFFFAOYSA-N

物化性质

• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,4-Dihydro-2H-1,4-benzoxazine-7-boronic acid pinacol ester
Synonyms: 7-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-1,4-benzoxazine

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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: 3,4-Dihydro-2H-1,4-benzoxazine-7-boronic acid pinacol ester
CAS number: 1361110-64-6

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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, 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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H20BNO3
Molecular weight: 261.1

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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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  7-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-3,4-二氢-2H-苯并[b][1,4]噁嗪 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 7-(3-amino-1H-indazol-4-yl)-N-phenyl-2H-benzo[b][1,4]oxazine-4(3H)-carboxamide
  参考文献：
  名称：

  Discovery of a New Series of Naphthamides as Potent VEGFR-2 Kinase Inhibitors

  摘要：

  Inhibition of VEGFR-2 signaling pathway has already become one of the most promising approaches for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of a new series of naphthamides as potent inhibitors of VEGFR-2. Among these compounds, 14c exhibited high VEGFR-2 inhibitory potency in both enzymatic and HUVEC cellular proliferation assays, with IC50 values of 1.5 and 0.9 nM, respectively. Kinase selectivity profiling revealed that 14c was a multitargeted inhibitor, and it also exhibited good potency against VEGFR-1, PDGFR-beta, and RET. Furthermore, 14c effectively blocked tube formation of HUVEC at nanomolar level. Overall, 14c might be a promising candidate for the treatment of cancer.

  DOI：

  10.1021/ml5000417
• 作为产物：
  描述：

  2-硝基-5-溴苯酚 在 1,1'-双(二苯基膦)二茂铁 、 硼烷四氢呋喃络合物 、 potassium acetate 、 铁粉 、 氯化铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 乙腈 为溶剂， 反应 5.5h， 生成 7-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-3,4-二氢-2H-苯并[b][1,4]噁嗪
  参考文献：
  名称：

  Discovery of a New Series of Naphthamides as Potent VEGFR-2 Kinase Inhibitors

  摘要：

  Inhibition of VEGFR-2 signaling pathway has already become one of the most promising approaches for the treatment of cancer. In this study, we describe the design, synthesis, and biological evaluation of a new series of naphthamides as potent inhibitors of VEGFR-2. Among these compounds, 14c exhibited high VEGFR-2 inhibitory potency in both enzymatic and HUVEC cellular proliferation assays, with IC50 values of 1.5 and 0.9 nM, respectively. Kinase selectivity profiling revealed that 14c was a multitargeted inhibitor, and it also exhibited good potency against VEGFR-1, PDGFR-beta, and RET. Furthermore, 14c effectively blocked tube formation of HUVEC at nanomolar level. Overall, 14c might be a promising candidate for the treatment of cancer.

  DOI：

  10.1021/ml5000417

文献信息

• [EN] PIPERIDIN-1- YL-N-PYRYDI NE-3-YL-2-OXOACET AM IDE DERIVATIVES USEFUL FOR THE TREATMENT OF MTAP-DEFICIENT AND/OR MT A-ACCUMULATING CANCERS<br/>[FR] DÉRIVÉS DE PIPÉRIDIN-1-YL-N-PYRYDINE-3-YL-2-OXO-ACÉTAMIDE UTILES POUR LE TRAITEMENT DE CANCERS DÉFICIENTS EN MTAP ET/OU ACCUMULANT MTA
  申请人：TANGO THERAPEUTICS INC

  公开号：WO2022026892A1

  公开（公告）日：2022-02-03

  Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R6, R7, R8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式（I）提供化合物及其药用盐，以及药物组合物；其中R1、R2、R3、R4、R6、R7、R8和n的定义如本文所述。本发明的化合物被认为对预防和治疗各种疾病条件有用。
• Catalytic 2-Ethylhexanoic Acid Promotes Mild Miyaura Borylations
  作者：Brittany M. Klootwyk、J. Craig Ruble、Graham R. Cumming、Eric M. Woerly

  DOI：10.1021/acs.joc.4c00280

  日期：2024.4.19

  Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as

  据报道，使用碳酸钾和 5 mol% 2-乙基己酸的组合在 25 °C 下对芳基和杂芳基氯化物和溴化物进行 Miyaura 硼化。在这些条件下原位产生催化量的2-乙基己酸钾避免了在反应设置期间对化学计量量的吸湿性2-乙基己酸钾的特殊处理的需要以及在产物分离期间除去所得羧酸的困难。
• Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline
  作者：Manhong Li、Yi-Hui Deng、Qianqian Chang、Jinyuan Li、Chao Wang、Leifeng Wang、Tian-Yu Sun

  DOI：10.3390/molecules29081783

  日期：——

  Due to boron’s metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple and readily available starting materials still remains a challenge. In this

  由于硼的类金属特性，芳香硼试剂是常用的合成中间体。用于生产芳香硼化合物的芳基CH键的直接硼基化提供了一种有吸引力的一步解决方案。尽管该领域取得了重大进展，但使用简单易得的起始材料实现区域选择性芳基CH键硼化仍然是一个挑战。在这项工作中，我们试图通过选择不同的碱基来代替我们之前研究中使用的有机碱（NEt3）来增强电子供体受体（EDA）复合物的反应活性。令我们高兴的是，当使用 NH4HCO3 作为碱时，我们实现了温和的可见光介导的芳香族 CH 键硼化反应，具有出色的区域选择性（rr > 40:1 对单一异构体）。与我们之前的硼化方法相比，该方案通过使用 N-溴代琥珀酰亚胺为芳基 CH 键硼化提供了更有效和更广泛的范围。该方案具有良好的官能团耐受性和出色的区域选择性，能够实现多种生物学相关化合物的功能化和新颖的级联转化。本研究进行的机理实验和理论计算表明，对于某些芳烃，芳基CH键硼基化可能通过一
• [EN] STEROID COMPOUND, AND PHARMACEUTICAL COMPOSITION THEREOF AND USE THEREOF<br/>[FR] COMPOSÉ STÉROÏDE, COMPOSITION PHARMACEUTIQUE ET UTILISATION ASSOCIÉES<br/>[ZH] 甾体类化合物、其药物组合物及其应用
  申请人：[en]JIANGSU SIMCERE PHARMACEUTICAL CO., LTD.;[zh]江苏先声药业有限公司

  公开号：WO2022268176A1

  公开（公告）日：2022-12-29

  一种式(I)所示化合物或其药学上可接受的盐、药物组合物及其制备方法，以及其在治疗肿瘤、炎性疾病或自身免疫性疾病中的用途。
• Imidazo[1,2-<i>a</i>]pyridines: Orally Active Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor
  作者：Andrés A. Trabanco、Gary Tresadern、Gregor J. Macdonald、Juan Antonio Vega、Ana Isabel de Lucas、Encarnación Matesanz、Aránzazu García、María Lourdes Linares、Sergio A. Alonso de Diego、José Manuel Alonso、Daniel Oehlrich、Abdelah Ahnaou、Wilhelmus Drinkenburg、Claire Mackie、José Ignacio Andrés、Hilde Lavreysen、José María Cid

  DOI：10.1021/jm201561r

  日期：2012.3.22

  Advanced leads of an imidazopyridine series of positive allosteric modulators of the metabotropic glutamate 2 (mGlu2) receptor are reported. The optimization of in vitro ADMET and in vivo pharmacokinetic properties led to the identification of 27o. With good potency and selectivity for the mGlu2 receptor, 270 affected sleep-wake architecture in rats after oral treatment, which we have previously shown to be indicative of mGlu2 receptor-mediated central activity.