1-Boc-3-溴吲哚 | 143259-56-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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-3-溴吲哚
• 中文别名: 3-溴吲哚-1-羧酸丁酯；1-N-BOC-3-溴吲哚；N-Boc-7-溴吲哚
• 英文名称: tert-butyl 3-bromo-1H-indole-1-carboxylate
• 英文别名: N-Boc-3-bromoindole；1-Boc-3-bromoindole；tert-butyl 3-bromoindole-1-carboxylate
• CAS: 143259-56-7
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: DMNYMGSBBRRGOW-UHFFFAOYSA-N

物化性质

• 沸点：
  367.9±34.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Boc-3-bromoindole
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: 1-Boc-3-bromoindole
CAS number: 143259-56-7

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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, refrigerated.
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: C13H14BrNO2
Molecular weight: 296.2

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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, hydrogen bromide.

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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-3-溴吲哚 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 生成 di-tert-butyl-3,3′-(4-methoxy-1-(methoxycarbonyl)-2,5-dioxocyclopent-3-ene-1,3-diyl)bis(1H-indole-1-carboxylate)
  参考文献：
  名称：

  Total Synthesis of Asterredione

  摘要：

  The first total synthesis of asterredione was efficiently accomplished over five linear steps and in 21.5% overall yield. As the crucial step, the 2-quaternary 1,3-cyclopentenedione skeleton of asterredione was readily achieved using the Darzens/ring-expansion strategy developed in our laboratory. The structure of synthesized asterredione was fully confirmed by X-ray crystallography.

  DOI：

  10.1021/jo4028177
• 作为产物：
  描述：

  1-Boc-吲哚 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到1-Boc-3-溴吲哚
  参考文献：
  名称：

  联合导演的邻位和远程金属化铃木交叉偶联策略。从联芳基O-氨基甲酸酯高效合成杂芳基融合的苯并吡喃酮

  摘要：

  杂芳基的简明合成dibenzopyranones图9a，b，10a中，b，图11A - Ç，和12A - ç已由杂联芳基的LDA诱导的迁移实现ø -carbamates 18，21，25，和30，这反过来，分别为使用组合的定向正交锂化（DoM）-过渡金属催化的Suzuki交叉偶联策略可以高收率制备。通往多种杂环的有效且通用的途径，包括香豆素19a和c从而实现了以前未知的异硫代库姆斯坦环系统22b。

  DOI：

  10.1021/jo900146d

文献信息

• Nickel‐Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry
  作者：Dong Liu、Hong‐Xing Ma、Ping Fang、Tian‐Sheng Mei

  DOI：10.1002/anie.201900956

  日期：2019.4

  Transition‐metal‐catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition‐metal‐catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel‐catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence

  过渡金属催化的偶联反应是合成芳基硫化合物的有用工具。但是，常规的过渡金属催化的芳基溴化物和氯化物的硫醇化反应通常需要在升高的反应温度下使用强碱。在此，我们报道了在室温下使用不分隔的电化学电池，在不存在外部碱的情况下，镍催化的芳基溴化物和氯化物的电化学催化硫醇化反应的第一个实例。
• A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates
  作者：Kai Kang、Nathan L. Loud、Tarah A. DiBenedetto、Daniel J. Weix

  DOI：10.1021/jacs.1c10907

  日期：2021.12.29

  medicine and materials science, the synthesis of biheteroaryls by cross-coupling remains challenging. We describe here a new, general approach to biheteroaryls: the Ni- and Pd-catalyzed multimetallic cross-Ullmann coupling of heteroaryl halides with triflates. An array of 5-membered, 6-membered, and fused heteroaryl bromides and chlorides, as well as aryl triflates derived from heterocyclic phenols,

  尽管它们对医学和材料科学很重要，但通过交叉偶联合成双杂芳基仍然具有挑战性。我们在这里描述了一种新的、通用的双杂芳基方法：杂芳基卤化物与三氟甲磺酸酯的 Ni 和 Pd 催化的多金属交叉 Ullmann 偶联。一系列 5 元、6 元和稠合杂芳基溴化物和氯化物，以及衍生自杂环酚的芳基三氟甲磺酸酯，被证明是该反应中可行的底物（62 个示例，平均产率为 63 ± 17%）。这种方法对双杂芳基的普遍性在 10 μmol 规模的 96 孔板格式中得到进一步证明。一组 96 种可能的产品在一组条件下提供了 >90% 的命中率。此外，可以使用配体、添加剂和还原剂的单个“工具箱板”快速优化低产率组合。
• Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
  作者：Karoline T. Neumann、Simon R. Laursen、Anders T. Lindhardt、Benny Bang-Andersen、Troels Skrydstrup

  DOI：10.1021/ol5007289

  日期：2014.4.18

  A general procedure for the palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides is reported, using near stoichiometric amounts of carbon monoxide. The method allows a broad substrate scope in moderate to excellent yields. The formed alkynone motive serves as a platform for synthesis of various heterocyclic structures, including pyrimidines. Furthermore, the presented strategy allows

  据报道，使用接近化学计量的一氧化碳，钯催化芳基溴化物的羰基化Sonogashira偶联反应的一般程序。该方法允许以中等至优异的产率在宽范围的基材上使用。形成的炔酮动机用作合成各种杂环结构（包括嘧啶）的平台。此外，提出的策略允许有效的13 C标记。
• Nickel‐Catalyzed <i>N</i> ‐Arylation of <i>NH</i> ‐Sulfoximines with Aryl Halides via Paired Electrolysis
  作者：Dong Liu、Zhao‐Ran Liu、Cong Ma、Ke‐Jin Jiao、Bing Sun、Lei Wei、Julien Lefranc、Simon Herbert、Tian‐Sheng Mei

  DOI：10.1002/anie.202016310

  日期：2021.4.19

  A novel strategy for the N‐arylation of NH‐sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and

  通过合并镍催化和电化学反应（在未分池中），开发了一种新的NH-亚砜肟亚胺的N-芳基化策略，从而为构建亚磺酰亚胺衍生物提供了一种实用的方法。在该协议中采用了配对电解，因此不需要牺牲阳极。由于温和的反应条件，获得了优异的官能团耐受性和产率。初步的机理研究表明，在室温下，Ni II物种的阳极氧化对于促进从所得Ni III物种中还原性消除C-N键至关重要。
• Divergent Synthesis of Cyclopropane-Containing Lead-Like Compounds, Fragments and Building Blocks through a Cobalt Catalyzed Cyclopropanation of Phenyl Vinyl Sulfide
  作者：Stephen J. Chawner、Manuel J. Cases-Thomas、James A. Bull

  DOI：10.1002/ejoc.201701030

  日期：2017.9.15

  space for drug discovery. A cobalt‐catalyzed cyclopropanation of phenyl vinyl sulfide affords these scaffolds on multigram scale. Divergent, orthogonal derivatization is achieved through hydrolysis, reduction, amidation and oxidation reactions as well as sulfoxide–magnesium exchange/functionalization. The cyclopropyl Grignard reagent formed from sulfoxide exchange is stable at 0 °C for > 2 h, which enables

  环丙烷为药物化学提供了重要的设计元素，并广泛存在于药物化合物中。在这里，我们描述了一种策略和广泛的合成研究，用于利用单一前体制备多种含环丙烷的类铅化合物、片段和结构单元。双官能环丙烷（E/Z）-乙基2-（苯硫基）-环丙烷-1-羧酸酯的设计允许通过酯和硫醚官能团衍生化为拓扑变化的化合物，旨在适应药物发现所需的化学空间。苯基乙烯基硫醚的钴催化环丙烷化反应可提供多克规模的支架。通过水解、还原、酰胺化和氧化反应以及亚砜-镁交换/功能化实现发散正交衍生化。由亚砜交换形成的环丙基格氏试剂在 0 °C 下稳定> 2 小时，这使得能够捕获各种亲电子试剂和 Pd 催化的 Negishi 交叉偶联反应。使用 LLAMA（先导化合物和分子分析）软件对亲脂性 (ALog P)、分子量和分子形状参数对制备的文库以及进一步的虚拟阐述进行分析，以说明生成先导化合物的成功化合物和片段。