3-氰基-[1,1-联苯]-4-羧酸甲酯 | 89900-92-5

• 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: 3-氰基-[1,1-联苯]-4-羧酸甲酯
• 英文名称: methyl 1-(3'-cyano-biphenyl-4-yl)-carboxylate
• 英文别名: methyl 3′-cyano-[1,1′-biphenyl]-4-carboxylate；methyl 3’-cyano-[1,1’-biphenyl]-4-carboxylate；methyl 3'-cyano-[1,1'-biphenyl]-4-carboxylate；methyl 4-(3-cyanophenyl)-benzoate；Methyl 4-(3-cyanophenyl)benzoate
• CAS: 89900-92-5
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: KPNDONDAUMRIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-(3-cyanophenyl)benzoate
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: Methyl 4-(3-cyanophenyl)benzoate
CAS number: 89900-92-5

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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: C15H11NO2
Molecular weight: 237.3

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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：

  3-氰基-[1,1-联苯]-4-羧酸甲酯 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以88%的产率得到3-氰基-[1,1-联苯]-4-羧酸
  参考文献：
  名称：

  组蛋白甲基转移酶SET7小分子抑制剂的发现，化学优化和生物学评估研究

  摘要：

  组蛋白的翻译后修饰，包括组蛋白甲基化和去甲基化，控制着多个基因的表达开关。包含SET结构域的赖氨酸甲基转移酶7（SET7）是唯一的甲基转移酶，它可以使组蛋白H3（H3K4me1）的赖氨酸4特异性单甲基化，并在多种疾病（包括乳腺癌，丙型肝炎病毒（HCV），动脉粥样硬化性血管疾病）中发挥关键作用，糖尿病，前列腺癌，肝细胞癌和肥胖症。但是，几种已知的SET7抑制剂表现出弱活性或差的选择性。因此，迫切需要开发新型的SET7抑制剂并具有很大的临床价值。在这项研究中，我们确定了2-79通过基于结构的虚拟筛选和进一步的基于AlphaLISA的生化评估作为一种新型命中化合物。通过化学优化，确认合成的化合物DC21为有效的SET7抑制剂，IC 50值为15.93μM。DC21和SET7之间的相互作用也通过SPR实验进行了验证。特别地，DC21在细胞水平上抑制了MCF7细胞的增殖，IC 50值为25.84μM

  DOI：

  10.1016/j.bmcl.2020.127061
• 作为产物：
  描述：

  methyl 4-(((3-cyanophenyl)sulfonamido)methyl)benzoate 以 甲醇 为溶剂， 以21%的产率得到3-氰基-[1,1-联苯]-4-羧酸甲酯
  参考文献：
  名称：

  由无痕连接体引导的无金属芳基交叉偶联。

  摘要：

  无金属、高选择性的联芳基化合物的合成对有机合成提出了重大挑战。报道了一种有前景的（杂）联芳基新方法的范围和机制，该方法通过将芳基取代基与无痕磺酰胺连接体（光剪接）进行光化学融合来实现。用不同的反应条件研究光剪接并对不同的合成探针（40 个例子，包括一组杂环）进行比较表明，该反应具有令人惊讶的广泛范围，并且既不涉及金属也不涉及自由基。量子化学计算表明CC键是通过分子内光化学过程形成的，该过程涉及激发单线态和五元过渡态的遍历，因此具有一致的ipso-ipso耦合结果。这些结果表明，光剪接是一种独特的激发态芳基交叉偶联方法，可用于合成多种联芳基化合物。

  DOI：

  10.1002/chem.201903582

文献信息

• [EN] METHOD FOR THE METAL-FREE PREPARATION OF A BIARYL BY A PHOTOSPLICING REACTION AND THEIR USES<br/>[FR] PROCÉDÉ DE PRÉPARATION SANS MÉTAL D'UN BIARYLE PAR RÉACTION DE PHOTOCOLLAGE ET UTILISATIONS ASSOCIÉES
  申请人：LEIBNIZ INST FUER NATURSTOFF FORSCHUNG UND INFEKTIONSBIOLOGIE E V HANS KNOELL INST HKI

  公开号：WO2019101679A1

  公开（公告）日：2019-05-31

  The present invention relates to a method for the metal-free preparation of a biaryl compound by a photosplicing reaction and its use in the preparation of chemical compounds, preferably of active ingredients e.g. in the fields of pharmaceuticals and agrochemicals. In particular, it refers to a method for the regiocontrolled preparation of a biaryl compound of formula (I): Ar-Ar' by photochemically reacting a precursor compound of formula (II): Ar-L-Ar' to form a biaryl compound of general formula: Ar-L-Ar' (II) → Ar-Ar' (I) wherein Ar and Ar', independently of each other, represent an unsubstituted or substituted C6-C20 aryl group or a heteroaryl group with 5–20 ring atoms selected from carbon, nitrogen, oxygen and sulfur, and L represents a group –X–Y–Z– as defined herein. The biaryl compounds are generally suitable as intermediates or key building blocks in a very broad spectrum of organic chemical syntheses and their respective utilities. Their use within the field of synthesis of active ingredients is an aspect of the invention, and their use in the preparation of pharmaceutically active ingredients is particularly preferred.

  本发明涉及一种通过光切割反应无金属制备联芳烃化合物的方法，以及其在化学化合物制备中的用途，特别是在制药和农药领域中的活性成分的制备中的用途。具体而言，它涉及一种通过光化学反应化学前体化合物（II）：Ar-L-Ar'与形成一般式的联芳烃化合物（II）→Ar-Ar'（I）反应，从而实现联芳烃化合物（I）的区域控制制备的方法，其中Ar和Ar'分别表示未取代或取代的C6-C20芳基或由碳、氮、氧和硫选择的5-20个环原子的杂芳基，L表示如本文所定义的一个组-X-Y-Z-。这些联芳烃化合物通常适用于有机化学合成的广泛领域中的中间体或关键构建块，以及它们各自的用途。它们在活性成分合成领域中的用途是本发明的一个方面，它们在制备药用活性成分中的用途尤为理想。
• Use of functionalized onium salts as a soluble support for organic synthesis
  申请人：Vaultier Michel

  公开号：US20070043234A1

  公开（公告）日：2007-02-22

  The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A 1 + , X 1 − , wherein A 1 + represents a cation and X 1 − represents an anion.

  该发明涉及使用至少一个有机功能官能化的离子盐作为可溶性支持体，在至少一个有机溶剂的存在下，用于在均相相中通过至少一个所述有机功能的转化对分子进行有机合成。该离子盐使合成的分子能够被释放。该离子盐在室温下以液态或固态形式存在，符合以下公式A1+，X1−，其中A1+代表阳离子，X1−代表阴离子。
• Palladium-catalyzed decarbonylative Suzuki–Miyaura cross-coupling of amides by carbon–nitrogen bond activation
  作者：Tongliang Zhou、Chong-Lei Ji、Xin Hong、Michal Szostak

  DOI：10.1039/c9sc03169c

  日期：——

  cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on

  钯催化的铃木-宫浦交叉偶联或芳基卤化物广泛应用于合成化学中许多重要分子的合成，包括药物、聚合物和功能材料。在此，我们公开了第一个钯催化的酰胺脱羰 Suzuki-Miyaura 交叉偶联，通过选择性活化酰胺的 NC(O) 键来合成联芳基化合物。这种新方法依赖于催化循环的精确序列工程，其中脱羰作用发生在金属转移步骤之前。该反应与多种硼酸和酰胺相容，以高产率提供有价值的联芳基化合物（> 60 个实例）。DFT 研究支持涉及氧化加成、脱羰和金属转移的机制，并提供了对高 NC(O) 键激活选择性的见解。最重要的是，该反应确立了钯催化在酰胺键的联芳铃木-宫浦交叉偶联中的应用，并且应该能够设计出多种交叉偶联方法，其中钯可与传统的由芳基卤化物合成联芳基和拟卤化物。
• Synthesis of Highly Functionalized Triarylbismuthines by Functional Group Manipulation and Use in Palladium- and Copper-Catalyzed Arylation Reactions
  作者：Martin Hébert、Pauline Petiot、Emeline Benoit、Julien Dansereau、Tabinda Ahmad、Adrien Le Roch、Xavier Ottenwaelder、Alexandre Gagnon

  DOI：10.1021/acs.joc.6b00767

  日期：2016.7.1

  group tolerance. We report herein a detailed study on the preparation of highly functionalized triarylbismuth reagents by triple functional group manipulation and their use in palladium- and copper-catalyzed C-, N-, and O-arylation reactions.

  有机铋是一类有吸引力的有机金属试剂，可以从便宜且无毒的铋盐中获得。三芳基双变异蛋白由于其在空气和湿气中的稳定性以及对官能团的高度耐受性而特别受关注。我们在这里报告了通过三官能团操纵制备高度官能化的三芳基铋试剂的详细研究，以及它们在钯和铜催化的C-，N-和O-芳基化反应中的应用。
• Integration of borylation of aryllithiums and Suzuki–Miyaura coupling using monolithic Pd catalyst
  作者：A. Nagaki、K. Hirose、Y. Moriwaki、K. Mitamura、K. Matsukawa、N. Ishizuka、J. Yoshida

  DOI：10.1039/c5cy02098k

  日期：——

  Integration of the preparation of arylboronic esters via aryllithiums and Suzuki–Miyaura coupling using monolithic Pd catalyst without an intentionally added base was achieved. A continuous operation has been done successfully for over 21 hours.

  通过使用整体式Pd催化剂而无需有意添加碱的情况下，通过芳基锂和Suzuki-Miyaura偶联制备芳基硼酸酯的过程得以实现。连续操作已成功完成21个小时以上。