(S)-1-苄基-3-氨基哌啶 | 168466-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (S)-1-苄基-3-氨基哌啶
• 中文别名: (S)-3-氨基-1-苄基哌啶；(S)-1-苄基3-氨基哌啶
• 英文名称: (S)-1-benzyl-3-aminopiperidine
• 英文别名: (S)-1-benzylpiperidin-3-amine；(S)-3-amino-1-benzyl-piperidine；(S)-1-phenylmethyl-3-aminopiperidine；(3S)-1-benzylpiperidin-3-amine
• CAS: 168466-85-1
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: HARWNWOLWMTQCC-LBPRGKRZSA-N

物化性质

• 沸点：
  281.2±33.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)
• 溶解度：
  易溶于乙醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
(S)-1-Benzyl-3-aminopiperidine
Product Name:
Synonyms:

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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.
(S)-1-Benzyl-3-aminopiperidine
Ingredient name:
CAS number: 168466-85-1

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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.
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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H18N2
Molecular weight: 190.3

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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：

  (S)-1-苄基-3-氨基哌啶 在 铁粉 、 氯化铵 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 24.2h， 生成 (S)-1-(1-benzylpiperidin-3-yl)-2-methyl-6-(phenylsulfonyl)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Discovery and Optimization of C-2 Methyl Imidazopyrrolopyridines as Potent and Orally Bioavailable JAK1 Inhibitors with Selectivity over JAK2

  摘要：

  Herein we report the discovery of the C-2 methyl substituted imidazopyrrolopyridine series and its optimization to provide potent and orally bioavailable JAK1 inhibitors with selectivity over JAK2. The C-2 methyl substituted inhibitor 4 exhibited not only improved JAK1 potency relative to unsubstituted compound 3 but also notable JAK1 vs JAK2 selectivity (20-fold and >33-fold in biochemical and cell-based assays, respectively). Features of the X-ray structures of 4 in complex with both JAK1 and JAK2 are delineated. Efforts to improve the in vitro and in vivo ADME properties of 4 while maintaining JAK1 selectivity are described, culminating in the discovery of a highly optimized and balanced inhibitor (20). Details of the biological characterization of 20 are disclosed including JAK1 vs JAK2 selectivity levels, preclinical in vivo PK profiles, performance in an in vivo JAK1-mediated PK/PD model, and attributes of an X-ray structure in complex with JAK1.

  DOI：

  10.1021/jm300628c
• 作为产物：
  描述：

  (S)-1-苄基-3-N-叔丁氧羰基氨基哌啶 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 (S)-1-苄基-3-氨基哌啶
  参考文献：
  名称：

  [EN] NOVEL HETEROCYCLIC COMPOUNDS AS ERK INHIBITORS
  [FR] NOUVEAUX COMPOSÉS HÉTÉROCYCLIQUES UTILISÉS COMME INHIBITEURS DE ERK

  摘要：

  本发明提供了一种化合物，其化学式为I：（此处应插入化学式 I），或其药用可接受的盐、溶剂或酯，其中 R、R1、R2 和 R3 如本文所定义。这些化合物是 ERK 抑制剂。还公开了包括上述化合物的药物组合物以及使用它们治疗癌症的方法。

  公开号：

  WO2011163330A1

文献信息

• Discovery of a PCAF Bromodomain Chemical Probe
  作者：Moses Moustakim、Peter G. K. Clark、Laura Trulli、Angel L. Fuentes de Arriba、Matthias T. Ehebauer、Apirat Chaikuad、Emma J. Murphy、Jacqui Mendez‐Johnson、Danette Daniels、Chun‐Feng D. Hou、Yu‐Hui Lin、John R. Walker、Raymond Hui、Hongbing Yang、Lucy Dorrell、Catherine M. Rogers、Octovia P. Monteiro、Oleg Fedorov、Kilian V. M. Huber、Stefan Knapp、Jag Heer、Darren J. Dixon、Paul E. Brennan

  DOI：10.1002/anie.201610816

  日期：2017.1.16

  bromodomain‐containing lysine acetyl transferases are members of subfamily I of the bromodomain phylogenetic tree. Iterative cycles of rational inhibitor design and biophysical characterization led to the discovery of the triazolopthalazine‐based L‐45 (dubbed L‐Moses) as the first potent, selective, and cell‐active PCAF bromodomain (Brd) inhibitor. Synthesis from readily available (1R,2S)‐(−)‐norephedrine furnished

  p300 / CBP相关因子（PCAF）和相关的GCN5含溴结构域的赖氨酸乙酰基转移酶是溴结构域系统发育树的亚家族I的成员。合理的抑制剂设计和生物物理特征的反复循环导致发现了基于三唑并噻嗪的L-45（称为L-Moses）作为第一种有效的，选择性的和具有细胞活性的PCAF溴结构域（Brd）抑制剂。由易于获得的（1R，2S）-（-）-去氧麻黄碱合成的对映纯形式的L-45。L-45显示出扰乱使用nanoBRET测定细胞PCAF-BRD组蛋白H3.3相互作用，和的共晶体结构L-45与来自恶性疟原虫的同源Brd PfGCN5的组合合理化了对PCAF和GCN5溴结构域的高选择性。化合物L-45在外周血单核细胞（PBMC）中没有可观察到的细胞毒性，在人和小鼠肝微粒体中没有良好的细胞渗透性和代谢稳定性，支持其在体内使用的潜力。
• HETEROCYCLIC COMPOUNDS, MEDICAMENTS CONTAINING SAID COMPOUNDS, USE THEREOF AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：HAMPRECHT Dieter

  公开号：US20140088097A1

  公开（公告）日：2014-03-27

  The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

  本发明涉及通式(I)的化合物及其互变异构体和盐，特别是药学上可接受的盐，它们具有有价值的药理学特性，特别是对上皮钠通道的抑制作用，以及它们用于治疗疾病，特别是肺部和呼吸道疾病的用途。
• The identification and use of robust transaminases from a domestic drain metagenome
  作者：Leona Leipold、Dragana Dobrijevic、Jack W. E. Jeffries、Maria Bawn、Thomas S. Moody、John M. Ward、Helen C. Hailes

  DOI：10.1039/c8gc02986e

  日期：——

  Transaminases remain one of the most promising biocatalysts for use in chiral amine synthesis, however their industrial implementation has been hampered by their general instability towards, for example, high amine donor concentrations and organic solvent content. Herein we describe the identification, cloning and screening of 29 novel transaminases from a household drain metagenome. The most promising

  转氨酶仍然是用于手性胺合成的最有前途的生物催化剂之一，然而，它们的工业实施因其普遍的不稳定性而受到阻碍，例如高胺供体浓度和有机溶剂含量。在此，我们描述了从家庭排水宏基因组中鉴定、克隆和筛选 29 种新型转氨酶。最有前途的酶得到了充分表征，并确定了 pH、温度、胺供体浓度和共溶剂的影响。几种酶表现出良好的底物耐受性以及对野生型转氨酶前所未有的稳健性。特别是一种酶很容易接受 IPA 作为胺供体，以 2-50 当量提供相同的转化率，并且能够耐受多种共溶剂，并且可以在高达 50% 的 DMSO 中操作——这一特性在野生型转氨酶。这项工作强调了利用宏基因组学在利基环境中发现生物催化剂的价值，并由此鉴定出迄今为止描述的最强大的天然转氨酶之一，在 IPA 和 DMSO 耐受性方面。
• Stereocontrolled dopamine receptor binding and subtype selectivity of clebopride analogues synthesized from aspartic acid
  作者：Jürgen Einsiedel、Klaus Weber、Christoph Thomas、Thomas Lehmann、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(03)00678-4

  日期：2003.10

  Employing the achiral 4-aminopiperidine derivative clebopride as a lead compound, chiral analogues were developed displaying dopamine receptor binding profiles that proved to be strongly dependent on the stereochemistry. Compared to the D1 receptor, the test compounds showed high selectivity for the D2-like subtypes including D2(long), D2(short), D3 and D4. The highest D4 and D3 affinities were observed

  利用非手性4-氨基哌啶衍生物clebopride作为先导化合物，开发了显示出多巴胺受体结合特征的手性类似物，事实证明该手性类似物强烈依赖于立体化学。与D1受体相比，测试化合物对D2类亚型（包括D2（长），D2（短），D3和D4）表现出高选择性。对于顺式-3-氨基-4-甲基吡咯烷3e和对映体ent3e观察到最高的D4和D3亲和力，分别导致K（i）值为0.23和1.8nM。从（S）-天冬氨酸及其非天然旋光对映体开始，以对映纯形式合成3型和5型苯甲酰胺。
• Derivatives of 3-hydroxy-pyrrole-2,4-dicarboxylic acid and uses thereof
  申请人：Cholody M. Wieslaw

  公开号：US20050026991A1

  公开（公告）日：2005-02-03

  Chemical agents of the general formula (I) and (II), such as derivatives of 3-hydroxy-pyrrole containing hydroxamic acid, and including salts thereof, that modulate levels of gene expression in cellular systems, including cancer cells, are disclosed, along with methods for preparing such agents, as well as pharmaceutical compositions containing such agents as active ingredients and methods of using these as therapeutic agents.

  揭示了一般式（I）和（II）的化学试剂，例如含有羟肟酸的3-羟基吡咯衍生物及其盐，这些试剂可以调节细胞系统中的基因表达水平，包括癌细胞。同时还公开了制备这些试剂的方法，以及含有这些试剂作为活性成分的药物组合物，以及使用这些试剂作为治疗剂的方法。