(3-溴吡啶-4-基)氨基甲酸叔丁酯 | 257937-08-9

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (3-溴吡啶-4-基)氨基甲酸叔丁酯
• 中文别名: (3-溴吡啶-4-基)氨甲酸叔-丁基酯
• 英文名称: tert-butyl (3-bromopyridin-4-yl)carbamate
• 英文别名: tert-butyl N-(3-bromopyridin-4-yl)carbamate
• CAS: 257937-08-9
• 化学式: C₁₀H₁₃BrN₂O₂
• 分子量: 273.129
• InChiKey: RPPLNTUECLIOOI-UHFFFAOYSA-N

物化性质

• 沸点：
  286.1±25.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,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: (3-Bromopyridin-4-yl)carbamic acid tert-butyl 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: (3-Bromopyridin-4-yl)carbamic acid tert-butyl ester
CAS number: 257937-08-9

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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, 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: C10H13BrN2O2
Molecular weight: 273.1

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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, 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：

  (3-溴吡啶-4-基)氨基甲酸叔丁酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 tert-butyl 2-methyl-1H-pyrrolo[3,2-c]pyridine-1-carboxylate
  参考文献：
  名称：

  氮杂吲哚的不对称加氢：由两个杂芳烃组成的稠合芳环系统的化学和对映选择性还原

  摘要：

  高对映选择性通过使用手性催化剂，将其从的[Ru（η制备的氮杂吲哚的氢化实现3 -methallyl）2（COD）]和反式-chelating双（膦）配体（PhTRAP）。脱芳香反应只发生在五元环上，因此相应的氮杂吲哚啉对映体比率高达97：3。

  DOI：

  10.1002/anie.201606083
• 作为产物：
  描述：

  4-(叔丁氧羰基氨基)吡啶 在 正丁基锂 、 四溴化碳 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(3-溴吡啶-4-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  新的吲哚基双膦酸酯的合成及其在PE / CA-PJ15细胞中的螯合能力评估

  摘要：

  双膦酸盐是最重要的一类抗吸收剂，可用于抗破骨细胞介导的骨质流失，最近在肿瘤学中也是如此。这些化合物对钙离子（Ca 2+）具有高亲和力，因此靶向骨矿物质，在这些地方矿物质似乎被骨吸收破骨细胞选择性内化并抑制破骨细胞功能。它们广泛用于医疗保健中，但是会受到严重副作用的影响。双膦酸酯的药理特性取决于其分子结构，这通常是肠道吸收差和分布低的原因。在这项工作中，我们合成了六种具有可变取代的吲哚部分的新型双膦酸酯化合物，以评估它们在PE / CA-PJ15细胞中的细胞外和细胞内钙螯合能力。初步的在硅片和体外ADME研究还进行和结果表明，吲哚部分在细胞渗透性和代谢性质中起重要作用。

  DOI：

  10.1016/j.ejmech.2015.08.019

文献信息

• Inhibitors of HCV replication
  申请人：Hudyma W. Thomas

  公开号：US20060046983A1

  公开（公告）日：2006-03-02

  Indole compounds of Formula I are described. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV. Different forms and compositions comprising the compounds are also described as well as methods of preparing the compounds.

  化合物I的吲哚类化合物已被描述。这些化合物对丙型肝炎病毒（HCV）具有活性，并可用于治疗感染HCV的人。还描述了包含这些化合物的不同形式和组成，以及制备这些化合物的方法。
• Pd-Catalyzed Asymmetric Dearomatization of Indoles via Decarbonylative Heck-Type Reaction of Thioesters
  作者：Ming-Liang Han、Wei Huang、Yu-Wen Liu、Min Liu、Hui Xu、Hai Xiong、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.0c03897

  日期：2021.1.1

  We report herein a palladium-catalyzed ligand-promoted asymmetric dearomatization of indoles via the decarbonylation of thioesters and the subsequent reductive Heck reaction. This protocol provides a facile and efficient way to construct an aza-quaternary stereocenter at the C2 position of indolines. A variety of functional groups and substitutions could be well tolerated, affording the substituted

  我们在本文中报道了通过硫酯的脱羰作用和随后的还原性Heck反应，钯催化的配体促进的吲哚的不对称脱芳香化作用。该协议为在二氢吲哚的C2位置构建氮杂四元立体中心提供了一种简便而有效的方法。可以很好地耐受各种官能团和取代基，从而提供具有高对映选择性的取代二氢吲哚。
• Novel fleximer pyrazole-containing adenosine analogues: chemical, enzymatic and highly efficient biotechnological synthesis
  作者：Anastasia Khandazhinskaya、Barbara Eletskaya、Ilja Fateev、Maria Kharitonova、Irina Konstantinova、Vladimir Barai、Alex Azhayev、Mervi T. Hyvonen、Tuomo A. Keinanen、Sergey Kochetkov、Katherine Seley-Radtke、Alex Khomutov、Elena Matyugina

  DOI：10.1039/d1ob01069g

  日期：——

  the heterocyclic purine base is split into its two components, i.e. pyrimidine and imidazole. Herein, we present a series of new pyrazole-containing flex-bases and the corresponding fleximer analogues of 8-aza-7-deaza nucleosides. Subsequent studies found that pyrazole-containing flex-bases are substrates of purine nucleoside phosphorylase (PNP). We have compared the chemical synthesis of fleximers and

  核苷类似物长期以来一直作为治疗病毒感染和癌症的关键化疗药物。与耐药性发展相关的问题导致人们寻找能够绕过靶酶结合位点点突变的核苷设计。作为对此问题的可能答案，Seley-Radtke 小组开发了一种柔性核苷支架（fleximers），其中杂环嘌呤碱基被分成两个组分，即嘧啶和咪唑。在此，我们提出了一系列新的含吡唑的柔性碱基和相应的 8-aza-7-deaza 核苷的柔性聚合物类似物。随后的研究发现，含吡唑的柔性碱基是嘌呤核苷磷酸化酶（PNP）的底物。我们比较了 Fleximers 的化学合成和使用分离酶的酶法以及使用过量生产 PNP 的大肠杆菌细胞。后者提供了立体化学纯的含吡唑的β- D-核糖-和β- D -2'-脱氧核糖-柔性聚合物，并且在环境问题方面是有益的，更经济，并且简化了化学方法所需的步骤。该反应在水中进行，避免了危险化学品，并使用水/乙醇混合物进行洗脱，通过离子交换色谱法分离产物。
• Radical Hydroarylation of Functionalized Olefins and Mechanistic Investigation of Photocatalytic Pyridyl Radical Reactions
  作者：Ciaran P. Seath、David B. Vogt、Zihao Xu、Allyson J. Boyington、Nathan T. Jui

  DOI：10.1021/jacs.8b10238

  日期：2018.11.14

  photoredox alkylation of halopyridines using functionalized alkene and alkyne building blocks. Selective single-electron reduction of the halogenated pyridines provides the corresponding heteroaryl radicals, which undergo anti-Markovnikov addition to the alkene substrates. The system is shown to be mild and tolerant of a variety of alkene and alkyne subtypes. A combination of computational and experimental

  我们报告了使用功能化烯烃和炔烃构建块的卤代吡啶的光氧化还原烷基化。卤化吡啶的选择性单电子还原提供了相应的杂芳基，这些杂芳基与烯烃底物发生反马尔科夫尼科夫加成。该系统表现出温和且耐受各种烯烃和炔烃亚型。计算和实验研究的结合支持涉及质子耦合电子转移的机制，然后是介质依赖性烯烃加成和由极性反转催化剂介导的快速氢原子转移。
• Synthesis of <i>N</i> ‐Heterocycles‐Fused Azasilines by Palladium‐Catalyzed Si‐Si Bond Activation
  作者：Ludovik Noël‐Duchesneau、Jacques Maddaluno、Muriel Durandetti

  DOI：10.1002/cctc.201900609

  日期：2019.8.21

  Azasilines fused nitrogen heterocycles are prepared in excellent yields (from 74 to 98 % according to the structures) for the first time in one operation with high regio‐ and stereoselectivities. The key step consists of an intramolecular palladium‐catalyzed cyclisation reaction of heteroaryl disilane cores, bearing double or triple bond. We first studied the reactivity of pyridyl heterocycles, using xylenes

  具有高区域选择性和立体选择性的首次操作以极高的收率（根据结构，从74％到98％）制备了氮杂氮杂环丙烷稠合的氮杂环。关键步骤包括分子内钯催化的带有双键或三键的杂芳基二硅烷核的环化反应。我们首先研究了吡啶基杂环的反应性，以二甲苯为溶剂，以Pd（dba）2 -P（OEt）3为催化剂，在130°C下进行。加合物的Z构型表明反应在合成后进行除炔烃外。然后通过从其他氮杂芳基化合物开始合成复杂的多杂环支架（吩噻嗪，吲哚，咔唑，喹啉和四氢喹啉）来说明该策略，以证明该方法的潜力，从而获得有前途的生物支架。