3-(N-甲基氨基羰基)苯硼酸频那醇酯 | 1197171-76-8

• 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-(N-甲基氨基羰基)苯硼酸频那醇酯
• 中文别名: 3-(N-甲基氨基氨基羰基)苯基硼酸,频哪醇酯
• 英文名称: N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• CAS: 1197171-76-8
• 化学式: C₁₄H₂₀BNO₃
• 分子量: 261.129
• InChiKey: YKVCWFPOJAXHGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

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

---

Section 1. Identification of the substance
Product Name: 3-(N-Methylaminocarbonyl)phenylboronic acid, pinacol ester
Synonyms: N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-(N-Methylaminocarbonyl)phenylboronic acid, pinacol ester
CAS number: 1197171-76-8

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C14H20BNO3
Molecular weight: 261.1

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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：

  3-(N-甲基氨基羰基)苯硼酸频那醇酯 在 copper(I) oxide 、 1,10-菲罗啉 、 potassium iodide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以62%的产率得到3-iodo-N-methylbenzamide
  参考文献：
  名称：

  通过铱催化的C–H硼化作用对芳烃进行立体控制的碘化

  摘要：

  报道了一种通过连续的C–H硼化和碘化制备芳基和杂芳基碘化物的温和方法。该过程的区域选择性由C–H硼化步骤中的空间效应控制，是对现有形成芳基碘化物的方法的补充。硼酸酯的碘化具有放射性标记的芳基碘化物的合成潜力，正如SPECT成像的潜在示踪剂的简明合成所证明的那样。

  DOI：

  10.1021/ol303164h
• 作为产物：
  描述：

  间溴苯甲酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 草酰氯 、 potassium acetate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-(N-甲基氨基羰基)苯硼酸频那醇酯
  参考文献：
  名称：

  芳基环丙胺-伏立诺他偶联物的癌细胞选择性靶向

  摘要：

  与传统的大分子药物递送系统相比，小分子抗癌药物递送具有许多优点。我们之前开发了苯基环丙胺 (PCPA)-药物缀合物 (PDC) 作为基于小分子的药物递送载体，用于靶向赖氨酸特异性脱甲基酶 1 (LSD1) 过表达的癌症。在本研究中，我们将这种 PDC 策略应用于 HDAC 抑制性抗癌药物伏立诺他 (vorinostat)。在三种合成的 PCPA 或芳基环丙胺 (ACPA)-伏立诺他缀合物1、9和32中，具有 4-氧苄基连接体的缀合物32在缓冲溶液中表现出足够的稳定性、有效的 LSD1 抑制、有效的 LSD1 依赖性伏立诺他释放以及有效和选择性的抗增殖作用对表达 LSD1 的人乳腺癌和小细胞肺癌细胞系的活性。这些结果表明缀合物在癌细胞中选择性地释放伏立诺他。类似的策略可能适用于其他抗癌药物。

  DOI：

  10.1021/acsmedchemlett.2c00126
• 作为试剂：
  描述：

  (3S,3'S)-4,4'-(7-氯吡啶并[2,3-D]嘧啶-2,4-二基)双(3-甲基吗啉) 、 3-(N-甲基氨基羰基)苯硼酸频那醇酯 在 3-(N-甲基氨基羰基)苯硼酸频那醇酯 作用下， 生成 非维匹仑
  参考文献：
  名称：

  WO2007060404A1

  摘要：

  公开号：

文献信息

• Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
  作者：Julien C. Vantourout、Robert P. Law、Albert Isidro-Llobet、Stephen J. Atkinson、Allan J. B. Watson

  DOI：10.1021/acs.joc.6b00466

  日期：2016.5.6

  The Chan–Evans–Lam reaction is a valuable C–N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan–Evans–Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found

  Chan–Evans–Lam反应是有价值的C–N键形成过程。但是，芳基硼酸频哪醇（BPin）酯试剂可能很难成为偶合剂，常常导致收率低，特别是在与芳基胺反应时。在此，我们报告了烷基-芳基胺与芳基BPin的Chan-Evans-Lam胺化反应的有效反应条件。发现混合的MeCN / EtOH溶剂系统可以使用芳基胺形成有效的C–N键，而烷基胺的偶联则不需要EtOH。
• [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS DE MANNOSE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：VERTEX PHARMA

  公开号：WO2013134415A1

  公开（公告）日：2013-09-12

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及用于治疗或预防细菌感染的化合物。这些化合物的公式为I：。发明还提供了包含这些化合物的药用可接受组合物，以及使用组合物治疗细菌感染的方法。最后，发明提供了制造本发明化合物的方法。
• Hydrogen Bond Directed <i>ortho</i> ‐Selective C−H Borylation of Secondary Aromatic Amides
  作者：Shao‐Tao Bai、Charles B. Bheeter、Joost N. H. Reek

  DOI：10.1002/anie.201907366

  日期：2019.9.9

  iridium catalyst for ortho‐selective C−H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen‐bond interactions. The BAIPy‐Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho‐C−H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety

  据报道是一种铱催化剂，可用于具有挑战性的二级芳族酰胺底物的邻位选择性CH硼化，其区域选择性受氢键相互作用的控制。所述BAIPy -Ir催化剂在至关重要的激活步骤形成与所述衬底三个氢键，并且允许邻-C-H硼化高选择性。该催化剂 对电子和空间特性不同的多种底物显示出空前的邻位选择性，并且该催化剂可耐受各种官能团。区域选择性CH硼化催化剂易于获得，并以高选择性和高转化率以克为单位转化底物。
• [EN] 1-AMINOSULFONYL-2-CARBOXYPYRROLE DERIVATIVES AS METALLO-BETA-LACTAMASE INHIBITORS<br/>[FR] DÉRIVÉS DE 1-AMINOSULFONYL-2-CARBOXYPYRROLE UTILISÉS EN TANT QU'INHIBITEURS DE MÉTALLO-BÊTA-LACTAMASE
  申请人：INFEX THERAPEUTICS LTD

  公开号：WO2021099793A1

  公开（公告）日：2021-05-27

  This invention relates to compounds of formula (I) and methods of treatment using the compounds. The compounds of the invention can be used in combination with antibacterial agents to treat bacterial infections. More specifically, the compounds of formula (I) can be used in combination with a class of antibacterial agents known as carbapenems. The novel compounds of the present invention are enzyme inhibitors and more particularly are metallo-β-lactamase inhibitors. (I)

  这项发明涉及公式（I）化合物及使用这些化合物进行治疗的方法。该发明的化合物可与抗菌药物结合，用于治疗细菌感染。更具体地，公式（I）化合物可与一类被称为碳青霉烯的抗菌药物结合使用。本发明的新型化合物是酶抑制剂，更具体地说是金属β-内酰胺酶抑制剂。
• Amide Effects in C−H Activation: Noncovalent Interactions with L-Shaped Ligand for <i>meta</i> Borylation of Aromatic Amides
  作者：Ranjana Bisht、Md Emdadul Hoque、Buddhadeb Chattopadhyay

  DOI：10.1002/anie.201809929

  日期：2018.11.26

  A new concept for the meta‐selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L‐shaped bifunctional ligand has been employed and engages in an O⋅⋅⋅K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction

  描述了芳族酰胺间选择性硼化的新概念。已经证明，尽管酯产生对硼烷基化，但是酰胺导致间硼烷基化。为了实现较高的间位选择性，使用了L型双功能配体，该配体与中度扭曲的酰胺羰基的氧原子发生O⋅⋅⋅K非共价相互作用。这种相互作用提供了对元CH活化/基化的特殊控制。