1-BOC-5-甲基吲哚-2-硼酸 | 475102-14-8

• 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: 1-BOC-5-甲基吲哚-2-硼酸
• 中文别名: 1-BOC-5-甲基-1H-吲哚-2-硼酸
• 英文名称: (1-(tert-butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronic acid
• 英文别名: [5-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid
• CAS: 475102-14-8
• 化学式: C₁₄H₁₈BNO₄
• 分子量: 275.112
• InChiKey: PEOOUPNYKOKTRH-UHFFFAOYSA-N

物化性质

• 熔点：
  112-116
• 沸点：
  456.8±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 储存条件：
  存储条件：2-8°C，需密封并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
1-BOC-5-methylindole-2-boronic acid
Product Name:
Synonyms: 1-t-Butoxycarbonyl-5-methylindole-2-boronic acid; 1-BOC-5-methyl-2-indoleboronic acid

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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
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
1-BOC-5-methylindole-2-boronic acid
Ingredient name:
CAS number: 475102-14-8

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H18BNO4
Molecular weight: 275.1

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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：

  1-BOC-5-甲基吲哚-2-硼酸 在 吡啶 、 四氮唑 、 palladium diacetate 、 sodium carbonate 、 二异丙胺 、 trisodium triphenylphosphine‐3,3′,3″‐trisulfonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 26.0h， 生成 β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose-3-(2-cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  DNA双链体和形成三链体的寡脱氧核苷酸结合了修饰的核苷，形成稳定且选择性的三链体†

  摘要：

  我们以前曾报道过含有非天然碱基三联体G-PPI·C3的DNA三链体，其中 生产者价格指数 是吲哚融合的 胞嘧啶 衍生物掺入DNA双链体中，C3是由三聚体形成的三链体形成寡核苷酸（TFO）的无碱基位点 丙烯链接器。在这项研究中，我们开发了一个新的非自然基础三合会A-ψ·C R1，其中ψ和C R1 是基本部分 2'-脱氧伪神经杜里定 和5-取代的 脱氧胞苷， 分别。我们检查了R1的几个吸电子取代基，发现5-溴胞嘧啶 （碳溴）可以选择性地识别ψ。此外，我们开发了新的生产者价格指数 衍生物， PPI我，在吲哚环上具有一个甲基，以便在结合了各种Watson-Crick碱基对的DNA双链体之间实现选择性的三链体形成，例如 TA， CG， -， 和 G-PPI我以及包含T，C， 碳溴和C3。我们使用紫外熔融和凝胶迁移率迁移分析研究了这些双链体和TFO之间的选择性三链体形成。

  DOI：

  10.1039/c1ob06411h
• 作为产物：
  描述：

  1-(叔丁氧羰基)-5-甲基吲哚 在 硼酸三异丙酯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到1-BOC-5-甲基吲哚-2-硼酸
  参考文献：
  名称：

  DNA双链体和形成三链体的寡脱氧核苷酸结合了修饰的核苷，形成稳定且选择性的三链体†

  摘要：

  我们以前曾报道过含有非天然碱基三联体G-PPI·C3的DNA三链体，其中 生产者价格指数 是吲哚融合的 胞嘧啶 衍生物掺入DNA双链体中，C3是由三聚体形成的三链体形成寡核苷酸（TFO）的无碱基位点 丙烯链接器。在这项研究中，我们开发了一个新的非自然基础三合会A-ψ·C R1，其中ψ和C R1 是基本部分 2'-脱氧伪神经杜里定 和5-取代的 脱氧胞苷， 分别。我们检查了R1的几个吸电子取代基，发现5-溴胞嘧啶 （碳溴）可以选择性地识别ψ。此外，我们开发了新的生产者价格指数 衍生物， PPI我，在吲哚环上具有一个甲基，以便在结合了各种Watson-Crick碱基对的DNA双链体之间实现选择性的三链体形成，例如 TA， CG， -， 和 G-PPI我以及包含T，C， 碳溴和C3。我们使用紫外熔融和凝胶迁移率迁移分析研究了这些双链体和TFO之间的选择性三链体形成。

  DOI：

  10.1039/c1ob06411h

文献信息

• Discovery and structure–activity relationship studies of indole derivatives as liver X receptor (LXR) agonists
  作者：Farid Bakir、Sunil Kher、Madhavi Pannala、Norma Wilson、Trang Nguyen、Ila Sircar、Kei Takedomi、Chiaki Fukushima、James Zapf、Kui Xu、Shao-Hui Zhang、Juping Liu、Lisa Morera、Lisa Schneider、Naoki Sakurai、Rick Jack、Jie-Fei Cheng

  DOI：10.1016/j.bmcl.2007.03.076

  日期：2007.6

  A structurally novel liver X receptor (LXR) agonist (1) was identified from internal compound collection utilizing the combination of structure-based virtual screening and high-throughput gene profiling. Compound 1 increased ABCA1 gene expression by eightfold and SREBP1c by threefold in differentiated THP-1 macrophage cell lines. Confirmation of its agonistic activity against LXR was obtained in the

  利用基于结构的虚拟筛选和高通量基因分析相结合的方法，从内部化合物收集中鉴定出一种结构新颖的肝X受体（LXR）激动剂（1）。在分化的THP-1巨噬细胞系中，化合物1使ABCA1基因表达增加了8倍，而SREBP1c增加了3倍。在辅助因子募集和报告基因反式激活测定中获得了其对LXR的激动活性的证实。描述了对化合物1的构效关系研究。
• [EN] PIPERIDINE DERIVATIVES FOR USE IN THE TREATMENT OR PREVENTION OF PSYCHIATRIC AND NEUROLOGICAL CONDITIONS<br/>[FR] DÉRIVÉS DE PIPÉRIDINE DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT OU LA PRÉVENTION DE TROUBLES PSYCHIATRIQUES ET NEUROLOGIQUES
  申请人：TAKEDA CAMBRIDGE LTD

  公开号：WO2015079224A1

  公开（公告）日：2015-06-04

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, in which R1, R2, R3, R4 and R5 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了式（I）化合物及其药用可接受盐，其中R1、R2、R3、R4和R5如规范中定义，其制备方法，含有它们的药物组合物以及它们在治疗中的应用。
• Isolation of a Natural Killer Group 2D Small‐Molecule Ligand from DNA‐Encoded Chemical Libraries
  作者：Sheila Dakhel、Andrea Galbiati、Francesca Migliorini、Claudia Comacchio、Sebastian Oehler、Luca Prati、Jörg Scheuermann、Samuele Cazzamalli、Dario Neri、Gabriele Bassi、Nicholas Favalli

  DOI：10.1002/cmdc.202200350

  日期：2022.11.4

  Isolation of NKG2D Hit from DEL screening. Compact single-pharmacophore two-building block DNA-Encoded Chemical Libraries (DELs) containing in total more than 1 million compounds were screened against site-selective immobilized Natural Killer Group 2D (NKG2D). Compound 17, preferential enriched after DEL selection experiments was identified and validated as ligand of NKG2D with affinity constant in

  从 DEL 筛选中分离 NKG2D 命中。针对位点选择性固定化 Natural Killer Group 2D (NKG2D) 筛选了包含总共超过 100 万种化合物的紧凑型单药团双结构单元 DNA 编码化学文库 (DEL)。在 DEL 选择实验后优先富集的化合物17被鉴定并验证为 NKG2D 的配体，其亲和常数在纳摩尔范围内。
• A Non-cryogenic Method for the Preparation of 2-(Indolyl) Borates, Silanes, and Silanols
  作者：Enrique Vazquez、Ian W. Davies、Joseph F. Payack

  DOI：10.1021/jo026087j

  日期：2002.10.1

  2-Indolyl borates are prepared via addition of LDA to a mixture of N-Boc-indole and triisopropyl borate at 0-5 degreesC. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).
• Identification of potent ITK inhibitors through focused compound library design including structural information
  作者：Matthias Herdemann、Isabelle Heit、Frank-Uwe Bosch、Gianluca Quintini、Claudia Scheipers、Alexander Weber

  DOI：10.1016/j.bmcl.2010.09.119

  日期：2010.12

  A series of novel compound libraries inhibiting interleukin-2 inducible T cell kinase (ITK) were designed, synthesized and evaluated. In the first design cycle two library scaffolds were identified showing low micromolar inhibition of ITK. Further iterative design cycles including crystal structure information of ITK and structurally related kinases led to the identification of indolylindazole and indolylpyrazolopyridine compounds with low nanomolar ITK inhibition. (C) 2010 Elsevier Ltd. All rights reserved.