4,4,5,5-四甲基-2-(4-甲基-3-硝基苯基)-1,3,2-二噁硼烷 | 1072945-06-2

• 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: 4,4,5,5-四甲基-2-(4-甲基-3-硝基苯基)-1,3,2-二噁硼烷
• 中文别名: 4-甲基-3-硝基苯硼酸频哪醇酯
• 英文名称: 4,4,5,5-tetramethyl-2-(4-methyl-3-nitrophenyl)-1,3,2-dioxaborolane
• CAS: 1072945-06-2
• 化学式: C₁₃H₁₈BNO₄
• mdl: MFCD09027080
• 分子量: 263.101
• InChiKey: XYZOZOWGODLRCW-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±35.0 °C(Predicted)
• 密度：
  1.13

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 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: 4-Methyl-3-nitrophenylboronic acid pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-2-(4-methyl-3-nitrophenyl)-1,3,2-dioxaborolane

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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-Methyl-3-nitrophenylboronic acid pinacol ester
CAS number: 1072945-06-2

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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: C13H18BNO4
Molecular weight: 263.1

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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：

  4,4,5,5-四甲基-2-(4-甲基-3-硝基苯基)-1,3,2-二噁硼烷 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以75%的产率得到3-氨基-4-甲基苯硼酸频呢醇酯
  参考文献：
  名称：

  Sandmeyer型转化合成三甲基锡烷基芳基硼酸酯化合物及其在化学选择性交叉偶联反应中的应用

  摘要：

  描述了一种基于Sandmeyer型反应的合成方法，可从硝基苯胺衍生物中获得锡和硼取代的芳烃。该转化可用于合成一系列官能化的三甲基锡烷基芳基硼酸酯。此外，还探索了Stille和Suzuki-Miyaura交叉偶联反应的化学选择性反应，并通过进行连续的一锅法式Stille和Suzuki-Miyaura交叉偶联反应合成了一系列m-和对-三苯基衍生物。

  DOI：

  10.1021/jo402618r
• 作为产物：
  描述：

  频哪醇 、 4-甲基-3-硝基苯硼酸 在 咪唑 、 iron(III) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到4,4,5,5-四甲基-2-(4-甲基-3-硝基苯基)-1,3,2-二噁硼烷
  参考文献：
  名称：

  Iron Catalysis and Water: A Synergy for Refunctionalization of Boron

  摘要：

  A new catalytic system has been optimized to promote the conversion of boron species into others. FeCl3 associated with imidazole and water favors boron refunctionalization under mild conditions.

  DOI：

  10.1055/s-0033-1340500

文献信息

• Structure-based design, synthesis, and evaluation of inhibitors with high selectivity for PARP-1 over PARP-2
  作者：Jiang Yu、Lingling Luo、Tong Hu、Yating Cui、Xiao Sun、Wenfeng Gou、Wenbin Hou、Yiliang Li、Tiemin Sun

  DOI：10.1016/j.ejmech.2021.113898

  日期：2022.1

  polymerase (PARP) inhibitors play a crucial role in cancer therapy. However, most approved PARP inhibitors have lower selectivity to PARP-1 than to PARP-2, so they will inevitably have side effects. Based on the different catalytic domains of PARP-1 and PARP-2, we developed a strategy to design and synthesize highly selective PARP-1 inhibitors. Compounds Y17, Y29, Y31 and Y49 showed excellent PARP-1 inhibition

  聚 (ADP-核糖) 聚合酶 (PARP) 抑制剂在癌症治疗中起着至关重要的作用。然而，大多数已获批准的 PARP 抑制剂对 PARP-1 的选择性低于对 PARP-2 的选择性，因此它们不可避免地会产生副作用。基于 PARP-1 和 PARP-2 的不同催化结构域，我们开发了一种设计和合成高选择性 PARP-1 抑制剂的策略。化合物Y17、Y29、Y31和Y49表现出优异的PARP-1抑制作用，其IC 50值分别为0.61、0.66、0.41和0.96 nM。然后，Y49（PARP-1 IC 50  = 0.96 nM，PARP-2 IC 50 = 61.90 nM，选择性 PARP-2/PARP-1 = 64.5) 被证明是最具选择性的 PARP-1 抑制剂。化合物Y29和Y49对 BRCA1 突变 MX-1 细胞的增殖抑制作用比其他癌细胞更强。在 MDA-MB-436 异种移植模型中
• Substituted Benzo-Imidazo-Pyrido-Diazepine Compounds
  申请人：Ashwell Mark A.

  公开号：US20120108574A1

  公开（公告）日：2012-05-03

  The present invention relates to substituted benzo-imidazo-pyrido-diazepine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted benzo-imidazo-pyrido-diazepine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及取代的苯并咪唑吡啶二氮杂化合物及其合成方法。本发明还涉及含有取代的苯并咪唑吡啶二氮杂化合物的药物组合物，以及通过向需要的主体施用这些化合物和药物组合物来治疗细胞增殖性障碍，如癌症的方法。
• Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions
  作者：Pavel B. Dzhevakov、Maxim A. Topchiy、Daria A. Zharkova、Oleg S. Morozov、Andrey F. Asachenko、Mikhail S. Nechaev

  DOI：10.1002/adsc.201500844

  日期：2016.3.17

  borylation and the one‐pot, two‐step homocoupling of aryl halides are reported for the first time. Bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] is an optimal source of palladium for Miyaura borylation, while for one‐pot two‐step homocoupling palladium(II) acetate [Pd(OAc)2] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The

  首次报道了宫浦硼化反应的无溶剂方案和芳基卤化物的一锅，两步均偶联。双（二亚苄基丙酮）钯（0）​​[Pd（dba）2 ]是用于宫浦硼酸化的最佳钯来源，而对于一锅两步均偶联的乙酸钯（II）[Pd（OAc）2 ]则可提供最高的收率。使用DPEphos配体可以最有效地偶联芳基溴化物。氯化物使用XPhos偶联。所开发的协议功能强大，用途广泛且易于大规模复制。
• 一种抑制组蛋白乙酰转移酶的化合物及其制 备方法与应用
  申请人：四川大学

  公开号：CN108358894B

  公开（公告）日：2021-05-07

  本发明属于有机合成医药领域，具体涉及抑制组蛋白乙酰转移酶的化合物，其结构如下：。通过该化合物的一些实施方案证实，能够对组蛋白乙酰转移酶p300产生较好的抑制作用，同时对肿瘤细胞具有很好的抑制作用，具有很好的药用潜力，为临床用药提供了一种新的潜在选择；同时，本发明提供的新化合物结构较多，合成线路多样，其制备方法简便，反应条件温和，便于操作和控制，能耗小，产率高，成本低，可适合产业化生产，制备得到的化合物生物活性较高，对肿瘤细胞的选择性强，类药性显著，具有广阔的市场前景。
• Substituted benzo[f]lmidazo[1,2-d]pyrido[2,3-b][1,4]diazepine compounds
  申请人：Ashwell Mark A.

  公开号：US08569331B2

  公开（公告）日：2013-10-29

  The present invention relates to substituted benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及取代的苯并[f]咪唑并[1,2-d]吡啶[2,3-b][1,4]二氮杂环化合物及其合成方法。本发明还涉及含有取代的苯并[f]咪唑并[1,2-d]吡啶[2,3-b][1,4]二氮杂环化合物的制药组合物，以及通过将这些化合物和制药组合物用于需要的受体中来治疗细胞增殖性疾病，如癌症的方法。