6-甲基吡啶-2-氨基甲酸叔丁酯 | 90101-22-7

• 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: 6-甲基吡啶-2-氨基甲酸叔丁酯
• 中文别名: (叔丁氧基)-n-甲基-n-[6-甲基-(2-吡啶)]羧酰胺；2-(Boc-氨基)-6-甲基吡啶
• 英文名称: 2-(tert-butoxycarbonylamino)-6-picoline
• 英文别名: (6-methyl-2-pyridinyl)carbamic acid,1,1-dimethylethyl ester；(tert-butoxy)-N-[6-methyl-(2-pyridyl)]carboxamide；2-[(t-butoxycarbonyl)amino]-6-methylpyridine；tert-butyl (6-methylpyridin-2-yl)carbamate；tert-butyl N-(6-methyl-2-pyridyl)carbamate；t-butyl (6-methyl-pyridin-2-yl)-carbamate；tert-butyl N-(6-methylpyridin-2-yl)carbamate
• CAS: 90101-22-7
• 化学式: C₁₁H₁₆N₂O₂
• mdl: MFCD07776935
• 分子量: 208.26
• InChiKey: XSVAARVWQDEAEL-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64°C
• 沸点：
  261.4±28.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 危险品标志：
  Xi
• 危险标志：
  GHS07
• 危险性描述：
  H302,H317
• 危险性防范说明：
  P280
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (6-Methyl-pyridin-2-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.
H302: Harmful if swallowed
H317: May cause an allergic skin reaction
P280: Wear protective gloves/protective clothing/eye protection/face protection

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Section 3. Composition/information on ingredients.
Ingredient name: (6-Methyl-pyridin-2-yl)-carbamic acid tert-butyl ester
CAS number: 90101-22-7

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C11H16N2O2
Molecular weight: 208.3

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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：

  6-甲基吡啶-2-氨基甲酸叔丁酯 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以95%的产率得到2-((tert-butoxycarbonyl)amino)-6-methylpyridine 1-oxide
  参考文献：
  名称：

  铜催化串联氧化重排-由醛和2-烷基杂环N-氧化物合成2-吡啶甲基酯衍生物

  摘要：

  使用简单的醛即可成功完成2-烷基吡啶，2-烷基吡嗪和2-烷基噻唑化合物的苄基C（sp 3）-H酰氧基化反应。这是通过铜催化的串联反应进行的，包括氧化酯化反应，然后通过O原子转移生成的高产率形成的Boekelheide中间体。该方法使得能够制备功能性杂环和2,6-二烷基吡啶的去对称化，从而有效地合成不对称的钳位配体，从而为更实用的布克海德重排提供了新的生命。

  DOI：

  10.1021/acs.orglett.7b03446
• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 、 碳酸二叔丁酯 以 叔丁醇 为溶剂， 以85%的产率得到6-甲基吡啶-2-氨基甲酸叔丁酯
  参考文献：
  名称：

  通过片段跳跃发现神经元一氧化氮合酶的高效选择性抑制剂

  摘要：

  选择性抑制神经元一氧化氮合酶 (nNOS) 已被证明可以预防脑损伤，并且对于治疗各种神经退行性疾病很重要。该研究表明，通过片段跳跃不仅可以获得更高的抑制效力和同工酶选择性，而且可以获得更多的药物特性。基于先导分子6的结构，片段跳跃有效地提取了 nNOS 活性位点中最少的药效成分，用于配体疏水和空间相互作用，并生成合适的亲脂性片段用于先导优化。在 20 种衍生物（化合物7 - 26）。我们用于 nNOS 和 SAR 分析的基于结构的抑制剂设计揭示了片段跳跃在先导发现和结构优化中的稳健性和效率，这意味着这种方法可以广泛应用于许多其他治疗靶点，而这些治疗靶点已知的药物样小分子调节剂仍然有限.

  DOI：

  10.1021/jm801220a

文献信息

• Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer’s Agents Based on Rational Design
  作者：Van-Hai Hoang、Phuong-Thao Tran、Minghua Cui、Van T. H. Ngo、Jihyae Ann、Jongmi Park、Jiyoun Lee、Kwanghyun Choi、Hanyang Cho、Hee Kim、Hee-Jin Ha、Hyun-Seok Hong、Sun Choi、Young-Ho Kim、Jeewoo Lee

  DOI：10.1021/acs.jmedchem.7b00098

  日期：2017.3.23

  proposed binding mode of the preferred substrate, Aβ3E−42. An in vitro structure–activity relationship study identified several excellent QC inhibitors demonstrating 5- to 40-fold increases in potency compared to a known QC inhibitor. When tested in mouse models of AD, compound 212 significantly reduced the brain concentrations of pyroform Aβ and total Aβ and restored cognitive functions. This potent Aβ-lowering

  谷氨酰胺基环化酶（QC）通过产生β淀粉样肽（pGlu-Aβ）的N末端焦谷氨酸与毒性淀粉样蛋白斑块的形成有关，因此可能参与了阿尔茨海默氏病（AD）的发病机理。我们基于优选底物Aβ3E-42的拟议结合模式设计了谷氨酰环化酶（QC）抑制剂库。一项体外结构-活性关系研究确定了几种出色的QC抑制剂，与已知的QC抑制剂相比，其效能提高了5至40倍。在AD的小鼠模型中测试时，化合物212显着降低了焦状Aβ和总Aβ的大脑浓度，并恢复了认知功能。这种强大的Aβ降低作用是通过将一个额外的结合区并入我们先前建立的药效团模型中而实现的，从而导致在QC结合位点与Glu327的羧酸酯基团发生强相互作用。我们的研究为设计新型QC抑制剂作为AD的潜在治疗方法提供了有用的见识。
• Vitronectin receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US06069158A1

  公开（公告）日：2000-05-30

  This invention relates to certain tricyclic compounds that are integrin receptor antagonists.

  本发明涉及某些三环化合物，它们是整合素受体的拮抗剂。
• Thrombin inhibitors
  申请人：——

  公开号：US20030158218A1

  公开（公告）日：2003-08-21

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: 1 wherein R 1 is, for example, hydrogen, Cl, or cyano, and R 2 is, for example, hydrogen, 2

  本发明的化合物在抑制凝血酶及相关血栓闭塞方面具有以下结构的有用： 1 其中R 1 例如是氢、氯或氰基，而R 2 例如是氢、 2
• Silver-Catalyzed Cyclization of<i>N</i>-(Prop-2-yn-1-yl)pyridin-2-amines
  作者：Mourad Chioua、Elena Soriano、Lourdes Infantes、M. Luisa Jimeno、José Marco-Contelles、Abdelouahid Samadi

  DOI：10.1002/ejoc.201201258

  日期：2013.1

  We report herein the silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-yl)pyridine-2-amines as a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines. The isomerization reactions proceeded under mild reactions conditions to give good yields and excellent regioselectivity. A DFT-based mechanistic analysis is also reported.

  我们在此报告了银催化的易于获得的 N-(prop-2-yn-1-yl)pyridine-2-amines 的环异构化作为合成不同取代的 3-methylimidazo[1,2-a ]吡啶。异构化反应在温和的反应条件下进行，具有良好的产率和优异的区域选择性。还报告了基于 DFT 的机械分析。
• Synthesis of 3-Aminoimidazo[1,2-<i>a</i>]pyridines from α-Aminopyridinyl Amides
  作者：Sophie Régnier、William S. Bechara、André B. Charette

  DOI：10.1021/acs.joc.6b01324

  日期：2016.11.4

  3-Aminoimidazo[1,2-a]pyridines are rapidly synthesized via a facile and mild cyclodehydration-aromatization reaction starting from readily available amides. The cyclodehydration step is mediated by the activation of N-Boc-protected 2-aminopyridine-containing amides by triflic anhydride (Tf2O) in the presence of 2-methoxypyridine (2-MeO-Py). Subsequently, the addition of K2CO3 in THF ensured a clean

  3-氨基咪唑并[1,2- a ]吡啶是通过容易和温和的环脱水-芳构化反应迅速合成的，从容易获得的酰胺开始。在2-甲氧基吡啶（2-MeO-Py）存在下，通过三氟甲磺酸酐（Tf 2 O）活化N -Boc保护的含2-氨基吡啶的酰胺来介导环脱水步骤。随后，添加K 2 CO 3在THF中的溶剂确保干净的脱保护-芳构化序列，以提供所需的杂环。在优化的程序下，可以容忍各种各样的官能团和取代模式，并且对于稠合的双环3-氮杂-杂环化合物，获得了良好或优异的收率。另外，发现该反应可扩展至克级，并且可以用未保护的无环酰胺前体进行。我们还发现，所得产物是Pd和Ru催化的CH芳基化反应的有价值的中间体，从而可以精制各种功能化的结构单元。