吲哚-7-硼酸 | 210889-31-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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-7-硼酸
• 英文名称: (1H-indol-7-yl)boronic acid
• 英文别名: indole-7-boronic acid；indol-7-ylboronic acid；1H-indol-7-ylboronic acid
• CAS: 210889-31-9
• 化学式: C₈H₈BNO₂
• 分子量: 160.968
• InChiKey: HABOMNOJYJNVHE-UHFFFAOYSA-N

物化性质

• 沸点：
  433.2±37.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  3
• 氢受体数：
  2

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Indole-7-boronic 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: Indole-7-boronic acid
CAS number: 210889-31-9

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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: C8H8BNO2
Molecular weight: 161.0

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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, 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

制备方法与用途

吲哚-7-硼酸

吲哚-7-硼酸是一种硼酸衍生物，在有机合成中广泛用于碳-碳键的形成。在Suzuki偶联反应中，芳基卤化物和硼酸芳基或乙烯基酯通过四(三苯基膦)钯（Pd(PPb)4）催化实现偶联。

制备

在无光条件下，在0℃且氩气气氛的烧瓶中，将62毫克钾氢化物(KH)悬浮于0.4毫升无水四氢呋喃(THF)中。随后加入300毫克7-溴吲哚溶解于2.6毫升无水THF中的溶液，并搅拌混合物15分钟。

待温度降至-78℃后，缓慢滴加预先冷却至相同温度的叔丁基锂在戊烷中浓度为3.1毫摩尔/毫升的溶液。将混合物恢复到室温并继续搅拌15分钟后再次冷却回-78℃。加入1.53毫摩尔的三甲基硼酸酯（B(OMe)3），再于室温下搅拌3小时。

最后，向反应混合物中加入5毫升水，并使用20毫升乙酸乙酯(EtAcO)分两次萃取。通过添加10％盐酸将水层pH值调整至1，并再次用20毫升乙酸乙酯萃取三次。合并的有机提取物经无水硫酸镁(MgSO4)干燥后过滤，蒸干溶剂得到浅棕色油状物形式的粗制吲哚-7-硼酸。

反应信息

• 作为反应物：
  描述：

  吲哚-7-硼酸 在 四(三苯基膦)钯 、 羟胺 、 sodium acetate 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced PEPCK activation

  摘要：

  Continuing studies based on dihydroquinoline glucocorticoid receptor agonists lead to the discovery of a series of C4-oxime analogs. Representative compounds exhibited potent transrepression activity with minimal transactivation of phosphoenolpyruvate caboxykinase (PEPCK), a key protein in the gluconeogenesis pathway. These compounds represent promising leads in identifying GR agonists with high anti-inflammatory activity and attenuated potential for glucose elevation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.104
• 作为产物：
  描述：

  7-溴吲哚 在 盐酸 、 potassium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 3.67h， 生成 吲哚-7-硼酸
  参考文献：
  名称：

  遷移金属化合物、オレフィン重合用触媒およびオレフィン系重合体の製造方法

  摘要：

  提供含有新型过渡金属化合物和优良的烯烃聚合活性的烯烃聚合用催化剂。采用以下化合物（D）代表的过渡金属化合物，以及包含该过渡金属化合物，最好包括有机金属化合物、有机铝氧化合物以及与上述过渡金属化合物反应形成离子对的化合物的烯烃系聚合体用催化剂。【选择图】无

  公开号：

  JP2015193612A

文献信息

• 유기 전기 발광 소자용 발광 재료, 이를 이용한 유기 전기 발광 소자 및 유기 전기 발광 소자용 재료
  申请人：CHOI,DON-SOO 최돈수(419990450773)

  公开号：KR102175379B1

  公开（公告）日：2020-11-09

  발광 파장 조절 및 발광 효율이 우수한 퓨즈드 화합물, 그의 제조방법 및 상기 퓨즈드 화합물을 포함하는 유기전자소자를 제시한다.

  发光波长调节和发光效率优异的融合化合物，以及其制备方法和包含所述融合化合物的有机电子器件。
• [EN] EP1 RECEPTOR LIGANDS<br/>[FR] LIGANDS DU RÉCEPTEUR EP1
  申请人：ESTEVE LABOR DR

  公开号：WO2013037960A1

  公开（公告）日：2013-03-21

  The present invention belongs to the field of EP1 receptor ligands. More specifically it refers to compounds of general formula (I) having great affinity and selectivity for the EP1 receptor. The invention also refers to the process for their preparation, to their use as medicament for the treatment and/or prophylaxis of diseases or disorders mediated by the EP1 receptor as well as to pharmaceutical compositions comprising them.

  本发明属于EP1受体配体领域。更具体地，它涉及具有对EP1受体具有很高亲和力和选择性的一般式(I)化合物。该发明还涉及它们的制备方法，以及它们作为治疗和/或预防由EP1受体介导的疾病或紊乱的药物的用途，以及包含它们的药物组合物。
• [EN] NOVEL PYRIDIN-2(1H)ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR THE TREATMENT OF PAIN<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRIDIN-2(1H)ONE, LEUR PRÉPARATION ET LEUR UTILISATION POUR LE TRAITEMENT DE LA DOULEUR
  申请人：INST NAT SANTE RECH MED

  公开号：WO2021064186A1

  公开（公告）日：2021-04-08

  The present invention concerns novel pyridin-2(1H)one derivatives, their process of preparation and their use in therapeutics, in particular as agents for treating and/or preventing pain.

  这项发明涉及新型吡啶-2(1H)酮衍生物，它们的制备过程以及它们在治疗学中的用途，特别是作为治疗和/或预防疼痛的药物。
• [EN] SUBSTITUTED TRIAZOLO QUINOXALINE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZOLO-QUINOXALINE SUBSTITUÉS
  申请人：GRUENENTHAL GMBH

  公开号：WO2020016453A1

  公开（公告）日：2020-01-23

  The present invention relates to compounds according to general formula (I) which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.

  本发明涉及符合一般式(I)的化合物，其作为糖皮质激素受体的调节剂，并可用于治疗和/或预防至少部分由糖皮质激素受体介导的疾病。
• [EN] MONOCYCLIC HETEROARYL SUBSTITUTED COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROARYLE MONOCYCLIQUE SUBSTITUÉS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018013772A1

  公开（公告）日：2018-01-18

  Disclosed are compounds of Formulas (I), (II), (III), (IV), (V), (VI), (VII), or (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII) or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a monocyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

  公开的是Formula（I）、（II）、（III）、（IV）、（V）、（VI）、（VII）或（VIII）的化合物：（I）（II）（III）（IV）（V）（VI）（VII）（VIII）或其立体异构体、互变异构体、药学上可接受的盐、溶剂合物或前药，其中R3是一个单环杂环芳基基团，其上取代零至3个R3a；R1、R2、R3a、R4和n在此处有定义。还公开了将这些化合物用作PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在抑制或预防血小板聚集方面很有用，并且可用于治疗血栓栓塞性疾病或血栓栓塞性疾病的初级预防。