苯基硼酸1,3-丙二醇酯 | 4406-77-3

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 苯基硼酸1,3-丙二醇酯
• 中文别名: 2-苯基-1,3,2-二氧硼杂环
• 英文名称: 2-Phenyl-1,3,2-dioxaborinane
• 英文别名: 2-Phenyl-1,3,2-dioxaborinan
• CAS: 4406-77-3
• 化学式: C₉H₁₁BO₂
• mdl: MFCD00075228
• 分子量: 161.996
• InChiKey: QLWMDSAMEIJLQB-UHFFFAOYSA-N

物化性质

• 沸点：
  106 °C2 mm Hg(lit.)
• 密度：
  1.077 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避免使用强氧化剂

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封，存放在阴凉干燥处，并在容器中充入氮气保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Phenyl-1,3,2-dioxaborinane
Synonyms:

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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
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Phenyl-1,3,2-dioxaborinane
CAS number: 4406-77-3

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.

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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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H11BO2
Molecular weight: 162.0

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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：

  苯基硼酸1,3-丙二醇酯 在 碘 、 氧气 、 potassium carbonate 作用下， 以 PEG-400 为溶剂， 反应 48.0h， 以47%的产率得到联苯
  参考文献：
  名称：

  有氧条件下 PEG-400 中碘促进芳基硼酸的高效同源偶联

  摘要：

  在有氧条件下，碘能够在 PEG-400 中以中等至良好的产率催化芳基硼酸的均偶联。这种不含过渡金属的催化体系价格低廉，实用性强。值得注意的是，通过添加水，我们的催化系统可以在温和条件（100 °C）下保持高活性。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）

  DOI：

  10.1002/ejoc.200900087
• 作为产物：
  描述：

  苯硼酸 以 氘代氯仿 、 正戊烷 为溶剂， 反应 0.3h， 生成 苯基硼酸1,3-丙二醇酯
  参考文献：
  名称：

  具有代表性的手性和手性硼酸酯利用酯交换反应的相对稳定性的比较研究

  摘要：

  进行了五个代表性手性和非手性硼酸酯与各种结构改性二醇的酯交换反应的比较研究，以定性地了解影响这些硼酸酯相对稳定性的因素。几个因素，例如螯合，构象，取代基的空间体积，杂环的大小和熵，都会影响酯交换反应的相对速率以及硼酸酯的稳定性。在这些硼酸酯中，发现pin烷二醇苯基硼酸酯是最稳定的硼酸酯，而 DIPT 硼酸酯似乎在热力学上是最不稳定的。观察到与位阻二醇的酯交换反应相对较慢，但是提供了热力学上更稳定的硼酸酯。衍生自硼酸酯 顺 -cyclopentanediols和双环[2.2.1]庚烷 外 ， 外切 -2,3-二醇是相对更稳定。这项研究不仅提供了各种硼酸酯相对稳定性的定性图，而且还提供了有关手性助剂可能回收的有用提示。许多 Ç 2 -对称的手性助剂，如2,3-丁二醇，2,4-戊二醇， DIPT ，并 顺 可以通过将相应的硼酸酯与市售廉价的二醇如频哪醇，1，3-丙二醇和新戊二醇进行简单的酯交换反应来回收-环己烷-1，2-二醇。

  DOI：

  10.1007/s00706-007-0699-x
• 作为试剂：
  描述：

  4-碘苯甲醚 、 苯甲酰胺 在 苯基硼酸1,3-丙二醇酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 以92%的产率得到N-茴香酰胺
  参考文献：
  名称：

  卷积聚合物镍催化从联芳形成到酰胺化

  摘要：

  通过聚（4-乙烯基吡啶）（P4VP）和氯化镍的分子卷积制备了稳定，可重复使用且不溶的聚（4-乙烯基吡啶）镍催化剂（P4VP-NiCl 2）。我们基于元素分析和Ni K-edge XANES提出了前催化剂中Ni中心的配位结构，并证实它与Ni K-edge EXAFS一致。使用P4VP-NiCl 2进行芳基卤化物和芳基硼​​酸酯的Suzuki-Miyaura型偶联（0.1mol％Ni）得到相应的联芳基化合物，产率高达94％。出人意料的是，当在酰胺存在下进行芳基卤化物和芳基硼​​酸/酯的相同反应时，酰胺化主要进行，从而以高达99％的产率得到相应的芳基酰胺。相反，在不存在芳基硼酸/酯的情况下，芳基卤化物和酰胺的反应没有进行。P4VP-NiCl 2成功地催化了内酰胺化反应，制备了菲啶酮。P4VP-NiCl 2被重复使用了五次，而催化活性没有明显损失。使用P4VP-NiCl 2有效合成药物，天然产物和

  DOI：

  10.1021/acscatal.0c03888

文献信息

• Nickel-catalyzed Conjugate Addition of Arylboron Reagents to α,β-Unsaturated Carbonyl Compounds with the Aid of a Catalytic Amount of an Alkyne
  作者：Eiji Shirakawa、Yuichi Yasuhara、Tamio Hayashi

  DOI：10.1246/cl.2006.768

  日期：2006.7

  Alkynes in combination with a catalytic amount of a nickel complex were found to catalyze the conjugate addition of arylboron reagents to α,β-unsaturated carbonyl compounds, where use of an optical...

  发现炔烃与催化量的镍络合物结合可催化芳基硼试剂与 α,β-不饱和羰基化合物的共轭加成，其中使用光学...
• [EN] 7-PHENYL-ISOQUINOLINE-5-SULFONYLAMINO DERIVATIVES AS INHIBITORS OF AKT (PROTEINKINASE B)<br/>[FR] DERIVES DE 7-PHENYL-ISOQUINOLINE-5-SULFONYLAMINO EN TANT QU'INHIBITEURS DE AKT (PROTEINE KINASE B)
  申请人：LILLY CO ELI

  公开号：WO2005054202A1

  公开（公告）日：2005-06-16

  The present invention relates to compounds Formula (I) as inhibitors of AKT activity, which are useful for the treatment of susceptible neoplasms and viral infections.

  本发明涉及化合物式（I）作为AKT活性抑制剂，用于治疗易感的肿瘤和病毒感染。
• [EN] BENZOFURAN COMPOUNDS HAVING ANTITUMOR ACTIVITY<br/>[FR] COMPOSES DE BENZOFURANE POSSEDANT UNE ACTIVITE ANTITUMORALE
  申请人：CHUGAI PHARMACEUTICAL CO LTD

  公开号：WO2004037816A1

  公开（公告）日：2004-05-06

  This invention relates to novel benzofuran compounds of the formula [I], wherein R1 and R2 are as defined in the claims and description, as well as pharmaceutically acceptable salts or solvates thereof, and to pharmaceutical compositions comprising such compounds and to processes for their preparation. The compounds have antitumor activity and are useful for the treatment of cancer.

  这项发明涉及公式[I]的新型苯并呋喃化合物，其中R1和R2如权利要求和描述中所定义，以及其药学上可接受的盐或溶剂合物，以及包含这种化合物的药物组合物和其制备方法。这些化合物具有抗肿瘤活性，并可用于癌症治疗。
• Three-Component Synthesis of Substituted η⁵-Cyclopentadienyltricarbonylrhenium Complexes:  Scope, Limitations, and Mechanistic Interpretations
  作者：Filippo Minutolo、John A. Katzenellenbogen

  DOI：10.1021/om990128t

  日期：1999.6.1

  with the rhenium precursor. Then, in the rate-determining step, the resulting preassociated rhenium−nucleophile intermediate reacts with C5H4N2 via a concerted SN2-like transition state. The same general mechanistic pathway seems to be followed by two very different classes of nucleophiles, carboxylates and boronic acids, in the synthesis of acyloxy- and carbon-substituted CpRe(CO)3 complexes, respectively

  我们研究了取代的CpRe（CO）3配合物“三组分”合成的范围和机理，该过程涉及亲核试剂与重氮环戊二烯（C 5 H 4 N 2）和fac -Re（CO）3 +物种的反应。 。我们发现只有中等强度的亲核试剂（卤素，羧酸盐，硼酸）适用于这种转化，并且它显示出对亲核试剂的空间和电子特征非常敏感。的效果的哈米特型ρσ分析对-该取代基与几种苯甲酸酯的相对速率的取代基表明，该反应通过供电子性取代基而加速。基于结构/反应性关系和NMR实验的机械分析表明，亲核试剂最初会与the前体反应。然后，在速率确定步骤中，所得预缔合的-亲核中间体通过协调的S N 2-过渡态与C 5 H 4 N 2反应。在酰氧基和碳取代的CpRe（CO）3的合成中，似乎遵循相同的一般机理途径，是截然不同的两类亲核试剂（羧酸盐和硼酸）配合物。特别地，硼酸酯缺乏反应性可以通过by与亲核试剂的去质子化的羟基之间的必要的预缔合步骤来解释，这仅对于游离硼酸是可能的。
• Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds
  作者：Ying Xia、Jianchun Wang、Guangbin Dong

  DOI：10.1021/jacs.8b02462

  日期：2018.4.25

  Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic

  在这里，我们描述了通过催化激活无张力的 CC 键，简单的酮可以在 Suzuki-Miyaura 偶联反应中有效地用作亲电子试剂。一系列常见的酮，如环戊酮、苯乙酮、丙酮和1-茚满酮，可以直接与各种芳基硼酸酯以高位点选择性偶联，这为获得更多功能化的芳香酮提供了独特的途径。初步机理研究表明酮 α-CC 键通过氧化加成断裂。

表征谱图