吲哚-2-硼酸频哪醇酯 | 476004-81-6

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 吲哚-2-硼酸频哪醇酯
• 中文别名: 1H-吲哚-2-硼酸频哪醇酯；吲哚-2-硼酸嚬哪醇酯
• 英文名称: 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole
• 英文别名: indole-2-boronic acid pinacol ester；1H-indole-2-boronic acid pinacol ester；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole；5,3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)-indole；2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS: 476004-81-6
• 化学式: C₁₄H₁₈BNO₂
• 分子量: 243.113
• InChiKey: IAQBURSQTCOSBP-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  396 °C
• 密度：
  1.11
• 闪点：
  193 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P273,P305+P351+P338
• 危险性描述：
  H315,H319,H335,H413
• 储存条件：
  2～8℃，干燥且密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Indole-2-boronic acid pinacol ester
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: Indole-2-boronic acid pinacol ester
CAS number: 476004-81-6

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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, under −20◦C.
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: C14H18BNO2
Molecular weight: 243.1

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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：

  吲哚-2-硼酸频哪醇酯 在 tris-(dibenzylideneacetone)dipalladium(0) potassium phosphate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 sodium hydroxide 、 三环己基膦 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-(1H-indol-2-yl)-1-methyl-N-[2-(piperidin-1-yl)ethyl]-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  NOVEL PYRAZOLE-3-CARBOXAMIDE DERIVATIVE HAVING 5-HT2B RECEPTOR ANTAGONIST ACTIVITY

  摘要：

  揭示的是由通式（I）表示的化合物或其药用可接受盐，其作为5-HT2B受体的选择性拮抗剂是有用的。该化合物和盐可用于治疗或预防与5-HT2B受体相关的各种疾病和症状。

  公开号：

  US20110275628A1
• 作为产物：
  描述：

  吲哚 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 13.17h， 生成 吲哚-2-硼酸频哪醇酯
  参考文献：
  名称：

  通过修饰硼取代基实现苯胺CHH烷基化中的高邻位选择性

  摘要：

  当使用B 2例如2（例如=乙二醇酯）代替B 2销2时，对苯胺的Ir催化C–H硼烷基化（CHBs）具有很高的邻位选择性，这是已知的异构体混合物。苯胺在4位上缺少封闭基团。通过这种修饰，对于各种苯胺，包括在2和3位有基团的苯胺，现在可以实现高选择性和高收率。实验表明，在CHB之前生成了ArylN（H）Beg物种，并且相对于B 2 pin 2支持了邻位选择性的提高。Ir催化剂上较小的Beg配体引起的反应。来自密度泛函理论计算分析的最低能级跃迁状态（TSs）在PhN（H）Beg和Beg配体中的O原子之间具有N–H··O氢键相互作用。PhN（H）Me与B 2例如2的Ir催化CHB也是高度邻位选择性的。1 H NMR实验表明，N-硼化在CHB之前完全生成PhN（Me）Beg。具有最低吉布斯能量的TS是邻位TS，其中Beg单元的取向与联吡啶配体相反。

  DOI：

  10.1021/acscatal.8b00641

文献信息

• Single-Site Cobalt-Catalyst Ligated with Pyridylimine-Functionalized Metal–Organic Frameworks for Arene and Benzylic Borylation
  作者：Rajashree Newar、Wahida Begum、Neha Antil、Sakshi Shukla、Ajay Kumar、Naved Akhtar、Balendra、Kuntal Manna

  DOI：10.1021/acs.inorgchem.0c00747

  日期：2020.8.3

  also significantly more robust and active than its homogeneous control, highlighting the beneficial effect of active-site isolation within the MOF framework that prevents intermolecular decomposition. The experimental and computational studies suggested (pyrim•−)CoI(THF) as the active catalytic species within the MOF, which undergoes a mechanistic pathway of oxidative addition, turnover limiting σ-bond

  我们报告了一种基于多孔且坚固耐用的吡啶基嘧啶功能化的金属有机骨架（pyrim-MOF）的高活性单中心非均相钴催化剂，用于芳烃和苄基CH键的化学选择性硼化。由U-O-68拓扑结构构成的嘧啶-MOF由锆-簇的二级结构单元和嘧啶基官能化的二羧酸桥接桥连接体构成，先用CoCl 2进行金属化，然后用NaEt 3 BH处理，得到钴官能化的MOF催化剂（pyrim- MOF-Co）。Pyrim-MOF-Co具有广泛的底物范围，允许使用B 2销2对卤素，烷氧基，烷基取代的芳烃以及杂环系统进行C–H硼化或用HBpin（pin =频哪醇酯）作为硼酸酯化剂，以高收率得到相应的芳烃或烷基硼酸酯。Pyrim-MOF-Co的营业额（TON）高达2500，并且可以循环使用至少9次。Pyrim-MOF-Co还比其均质控件强得多，并且更具活性，突出了在MOF框架内进行主动位点隔离以防止分子间分解的有益作用。实验和计算研究表明（pyrim
• Metal-organic frameworks containing nitrogen-donor ligands for efficient catalytic organic transformations
  申请人：The University of Chicago

  公开号：US10647733B2

  公开（公告）日：2020-05-12

  Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

  基于以氮为供体的有机桥联配体，包括基于1,3-二酮亚胺（NacNac）、联吡啶和柳酸亚胺的金属-有机框架（MOFs）组成物被合成，然后用金属前驱体如第一行过渡金属的络合物进行后合成金属化。有机桥联配体的金属络合物也可以直接并入MOFs中。MOFs提供了一个多功能的、可回收和可重复使用的单点固体催化剂家族，用于催化各种不对称有机转化。这些固体催化剂也可以集成到流动反应器或超临界流体反应器中。
• Noncovalent Interactions in Ir-Catalyzed C–H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
  作者：Md Emdadul Hoque、Ranjana Bisht、Chabush Haldar、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.7b04490

  日期：2017.6.14

  An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented

  描述了一种用于芳族酯的对位选择性硼化的有效策略。为了获得高的对位选择性，已经开发了一种新的催化体系，该体系改变了联吡啶的核心结构。有人提出，L型配体对于通过非共价相互作用识别酯羰基的氧原子的功能至关重要，这为超选择性C–H活化/硼化提供了空前的控制因素。
• 3,5-(Un)substituted-1H-pyrrolo[2,3-b]pyridine, 1H-pyrazolo[3,4-b]pyridine and 5H- pyrrolo[2,3-b]pyrazine dual ITK and JAK3 Kinase Inhibitors
  申请人：Arrien Pharmaceuticals LLC

  公开号：US20140315909A1

  公开（公告）日：2014-10-23

  The present invention relates to compounds described by Formula I: salts thereof, their synthesis, and their use as ITK and JAK3 inhibitors including such compounds and methods of using said compounds in the treatment of various diseases and or disorders such disease associated with abnormal cell growth such as autoimmune, inflammation, rheumatoid arthritis, systemic lupus erythematosus, atherosclerosis, ulcerative colitis, psoriatic arthritis, psoriasis, Crohn's, metabolic and cancer diseases. The present invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions and processes for preparing the compounds of the invention.

  本发明涉及由式I描述的化合物： 其盐，它们的合成，以及它们作为ITK和JAK3抑制剂的用途，包括这些化合物以及使用这些化合物治疗各种疾病和/或疾病的方法，这些疾病与异常细胞生长有关，如自身免疫、炎症、类风湿关节炎、系统性红斑狼疮、动脉粥样硬化、溃疡性结肠炎、银屑病性关节炎、银屑病、克罗恩病、代谢和癌症疾病。本发明还提供包括本发明化合物的药学上可接受的组合物以及使用这些组合物的方法和制备本发明化合物的方法。
• Direct Conversion of Pinacol Arylboronic Esters to Aryl Triolborates
  作者：Gao-Qiang Li、Shunsuke Kiyomura、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1246/cl.2011.702

  日期：2011.7.5

  Conversion of pinacol arylboronic esters 3 to aryl triolborates 5 via transesterification with 1,1,1-tris(hydroxymethyl)ethane (4) was established with the advantages of tolerance to various functional groups. Transesterification was carried out at 30–60 °C in dioxane in the presence of MOH (M = Na and K) and H2O. High yields were achieved for stable aryl triolborates 5.

  通过与1,1,1-三(羟甲基)乙烷（4）进行转酯化反应，将联苯酚芳基硼酸酯3转化为芳基三醇硼酸盐5的方法已被确立，其优点在于对各种官能团的耐受性。在二恶烷中，在MOH（M = Na和K）和H2O的存在下，于30–60°C进行转酯化反应，获得了高产率的稳定芳基三醇硼酸盐5。