4-N-庚基苯硼酸 | 256383-44-5

• 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-N-庚基苯硼酸
• 英文名称: 4-heptylphenylboronic acid
• 英文别名: (4-heptylphenyl)boronic Acid
• CAS: 256383-44-5
• 化学式: C₁₃H₂₁BO₂
• mdl: MFCD04039028
• 分子量: 220.12
• InChiKey: RFBUNLZEBLXJKX-UHFFFAOYSA-N

物化性质

• 熔点：
  50-70 °C(Solv: pentane (109-66-0))
• 沸点：
  357.0±35.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2931900090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-N-Heptylphenylboronic acid
Synonyms:

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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-N-Heptylphenylboronic acid
CAS number: 256383-44-5

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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: C13H21BO2
Molecular weight: 220.1

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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.

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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-N-庚基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2,2',3-trifluoro-4"-heptyl-4-nonylterphenyl
  参考文献：
  名称：

  Glendenning, Margaret E.; Goodby, John W.; Hird, Michael, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 1, p. 27 - 34

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯酚三氟甲基磺酸酯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 盐酸 、 potassium phosphate monohydrate 、 potassium hydrogen fluoride 、 palladium on activated charcoal 、 氢气 、 palladium diacetate 、 三乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 1.5h， 生成 4-N-庚基苯硼酸
  参考文献：
  名称：

  Design and synthesis of boronic acid inhibitors of endothelial lipase

  摘要：

  Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.043
• 作为试剂：
  描述：

  4-氯 3-碘-苯甲酸甲酯 、 1,2-difluoro-3-(2-(4-(hexyloxy)phenyl)ethynyl)benzene 在 正丁基锂 、 硼酸三丁酯 、 四(三苯基膦)钯 、 potassium carbonate 、 4-N-庚基苯硼酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 以40.2 %的产率得到
  参考文献：
  名称：

  具有大双折射和负介电各向异性的苯并恶唑封端液晶

  摘要：

  我们合成了具有大双折射和负介电各向异性的杂环液晶，即5–4-(2-(4-(烷氧基)苯基)-2,3-二氟苯基)苯并(d)恶唑衍生物(nPFO )。这些化合物显示出对映向列中间相，中间相范围较宽，为 45.9–84.0 °C（加热过程）和 61.3–119.6 °C（冷却过程）。与具有不同苯并恶唑末端结构取向的传统苯并恶唑化合物6PFB的参考类似物相比，化合物nPFO由于其二面角增加而大致具有较低的熔点和清亮点。同时，化合物nPFO表现出明显大的双折射（Δn，实验测量和DFT理论计算分别为0.28-0.39和0.39-0.48），这是由于分子中乙炔桥基团引起的π共轭增强。受益于较大的垂直偶极矩和取向角，nPFO显示出负介电各向异性 ( Δɛ )，范围为 -3.60 至 -4.10。这些化合物可以赋予商用负液晶混合物更大的Δn和更高的品质因数，这表明它们是合适的掺杂剂，可以进一步提高一些商用液晶混合物的性能。

  DOI：

  10.1016/j.molliq.2023.122859

文献信息

• Synthesis and biological activity of 2-aminoimidazole triazoles accessed by Suzuki–Miyaura cross-coupling
  作者：Samuel Reyes、Robert W. Huigens III、Zhaoming Su、Michel L. Simon、Christian Melander

  DOI：10.1039/c0ob00925c

  日期：——

  A pilot library of 2-aminoimidazole triazoles (2-AITs) was synthesized and assayed against Acinetobacter baumannii and methicillin-resistant Staphylococus aureus (MRSA). Results from these studies show that these new derivatives have improved biofilm dispersal activities as well as antibacterial properties against A. baumannii. With MRSA biofilms they are found to possess biofilm inhibition capabilities at low micromolar concentrations.

  合成了2-氨基咪唑并三氮唑（2-AITs）的先导库，并对其针对鲍曼不动杆菌和甲氧西林耐药金黄色葡萄球菌（MRSA）的活性进行了评估。研究结果显示，这些新衍生物不仅对A. baumannii具有增强的生物膜分散活性，还具有抗菌特性。在MRSA生物膜方面，它们在低微摩尔浓度下表现出生物膜抑制能力。
• Tandem Oxidative Ring Expansion for Synthesis of Dibenzocyclooctaphenanthrenes
  作者：Lu Yang、Hidenori Matsuyama、Sheng Zhang、Masahiro Terada、Tienan Jin

  DOI：10.1021/acs.orglett.0c01725

  日期：2020.7.2

  A novel tandem single-electron oxidative ring expansion reaction has been developed for the construction of the saddle-shaped polycyclic arenes fused with cyclooctatetraene, that is, dibenzo[3,4:7,8]cycloocta[1,2-l]phenanthrenes (dbCOTPs). The combination of Cu(OTf)2 catalyst with DDQ triggered the selective oxidation of o-biphenyl-tethered methylenecirculenes fused with a seven-membered ring, giving

  已经开发了一种新颖的串联单电子氧化环扩环反应，用于构建与环辛酸酯，即二苯并[3,4：7,8]环辛[1,2- l ]菲（ dbCOTP）。Cu（OTf）2催化剂与DDQ的结合触发了与七元环稠合的邻联苯系留亚甲基环的选择性氧化，从而形成了相应的八元环稠合的dbCOTP。当前的七元环到八元环的串联扩环是通过亚苄基部分的选择性单电子氧化，分子内螺环化和1,2-芳基迁移序列发生的。
• Self-organization of mesomeric–ionic hybrid heterocycles into liquid crystal phases: a new class of polar mesogens
  作者：Channabasaveshwar V. Yelamaggad、Manoj Mathews、Uma S. Hiremath、Doddamane S. Shankar Rao、Subbarao Krishna Prasad

  DOI：10.1039/b417506a

  日期：——

  The first mesoionic nematic and smectic A mesogens derived from sydnones that are characterized by both covalent and ionic features have been synthesized and evidenced by optical, calorimetric and X-ray diffraction studies.

  第一种来自辛烯酮的中离子向列相和层状A相介质已被合成，并通过光学、热量测量和X射线衍射研究进行了表征，这些介质具有共价和离子特征。
• The detection of chiral perturbations in ferroelectric liquid crystals induced by dopants with axially chiral 2,2′-spirobiindan-1,1′-dione cores
  作者：Qian Cui、Christa M. Huntley、Robert P. Lemieux

  DOI：10.1039/b900594c

  日期：——

  Chiral perturbations exerted by the dopants 6,6′-diheptyloxy-2,2′-spirobiindan-1,1′-dione (2) and 6,6′-diheptoyloxy-2,2′-spirobiindan-1,1′-dione (4) in the SmC phase of the liquid crystal host 4-(4′-heptyl[1,1′-biphen]-4-yl)-1-hexylcyclohexanecarbonitrile (NCB76) are investigated via (i) probe experiments using the structural analogue 5,5′-diheptyloxy-2,2′-spirobiindan-1,1′-dione (1) as chiral probe, and (ii) 2H NMR experiments using deuterated forms of 2 and NCB76. The results suggest that a probe experiment is more effective than 2H NMR in detecting chiral perturbations provided that the structure of the probe is similar to that of the chiral dopant, and that the chiral perturbations exerted by the dopant may be modeled as a ‘chiral field’ which is conceptually similar to the electric field exerted by a point charge that decays with increasing distance from the latter.

  通过以下方法研究了掺杂剂 6,6â²-二庚基氧基-2,2â²-螺茚满-1,1â²-二酮 (2) 和 6,6â²-二庚氧基-2,2â²-螺茚满-1,1â²-二酮 (4) 在液晶宿主 4-(4â²-庚基[1、1â²-联苯]-4-基）-1-己基环己烷甲腈（NCB76）进行了研究，方法是：(i) 使用结构类似物 5,5â²-diheptyloxy-2,2â²-spirobiindan-1,1â²-dione (1) 作为手性探针进行探针实验；(ii) 使用 2 和 NCB76 的氚化形式进行 2H NMR 实验。结果表明，在探测手性扰动方面，探针实验比 2H NMR 更有效，前提是探针的结构与手性掺杂剂的结构相似，而且掺杂剂产生的手性扰动可被模拟为 "手性场"，而 "手性场 "在概念上与点电荷产生的电场相似，随着与点电荷距离的增加而衰减。
• Glendenning, Margaret E.; Goodby, John W.; Hird, Michael, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 3, p. 481 - 491
  作者：Glendenning, Margaret E.、Goodby, John W.、Hird, Michael、Toyne, Kenneth J.

  DOI：——

  日期：——