4-(苄氧基)哌啶-1-羧酸叔丁酯 | 159557-47-8

• 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: 4-(苄氧基)哌啶-1-羧酸叔丁酯
• 英文名称: 4-benzyloxypiperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(benzyloxy)piperidine-1-carboxylate；tert-butyl 4-benzyloxypiperidine-1-carboxylate；4-benzyloxy-N-boc-piperidine；1-(tert-butoxycarbonyl)-4-benzyloxypiperidine；4-benzyloxy-1-tert-butoxycarbonyl-piperidine；tert-butyl 4-phenylmethoxypiperidine-1-carboxylate
• CAS: 159557-47-8
• 化学式: C₁₇H₂₅NO₃
• mdl: MFCD04972650
• 分子量: 291.39
• InChiKey: MWDHRTQFUAQSMK-UHFFFAOYSA-N

物化性质

• 沸点：
  383.8±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.588
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 4-(benzyloxy)piperidine-1-carboxylate
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: tert-Butyl 4-(benzyloxy)piperidine-1-carboxylate
CAS number: 159557-47-8

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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.
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: C17H25NO3
Molecular weight: 291.4

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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：

  4-(苄氧基)哌啶-1-羧酸叔丁酯 在 氢氧化钾 作用下， 以 异丙醇 为溶剂， 反应 14.0h， 以80%的产率得到4-(苄氧基)哌啶
  参考文献：
  名称：

  具有对乙酰胆碱酯酶和Abeta1-42聚集具有双重抑制作用的新型哌啶衍生物的合成，体外测定和分子建模，可用于阿尔茨海默氏病治疗。

  摘要：

  为了开发阿尔茨海默氏病疗法，我们设计并合成了具有乙酰胆碱酯酶（AChE）和β-淀粉样肽（Abeta）聚集抑制作用的新哌啶衍生物。为了与AChE的催化位点结合，设计了具有芳族基团的酯，对于外围位点，考虑了另一个芳族基团。为了插入淀粉样β-寡聚，考虑了与亲脂性基团的长且线性构象。用于具有双重作用的结构的合成方法取决于具有芳环的醇和取代的苯甲酸，它们在合成途径的最后一步被酯化。我们通过对乙酰胆碱酯酶，丁酰胆碱酯酶（BChE）的抑制试验筛选了这些新衍生物，和Abeta（1-42）肽聚集，AChE诱导的Abeta（1-42）聚集。我们的结果表明，化合物12显示出最佳的AChE抑制能力和选择性，而化合物29显示出最高的BChE抑制选择性。化合物15和12具有针对Abeta（1-42）聚合和AChE诱导的Abeta聚合的抑制活性。在对接模型中，我们确认了12的4-氯苯与AChE底部峡谷中Trp84的吲哚

  DOI：

  10.1016/j.bmc.2007.07.003
• 作为产物：
  描述：

  4-羟基哌啶 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 34.5h， 生成 4-(苄氧基)哌啶-1-羧酸叔丁酯
  参考文献：
  名称：

  三烷基胺N-CH3基团选择性C-H官能化中的逆热力学氢原子提取

  摘要：

  我们报告了一个简单的一锅法，它提供了 N-甲基-N,N-二烷基胺中 N-CH3 基团的功能化，对 N-CH2R 或 N-CHR2 基团具有高选择性。通过用三芳基胺盐氧化 DABCO 原位制备的自由基阳离子 DABCO+• 从 N-CH3 基团中影响高选择性和逆热力学 CH 提取。产生的中间体在一个锅中与有机金属亲核试剂原位反应，提供新的和高度选择性的 N-CH3 基团同系化。证明了试剂的化学选择性、可扩展性和可回收性，并通过计算和实验结果证实了机制建议。转化的效用在天然产物和药物的后期位点选择性功能化中得到证明，

  DOI：

  10.1021/jacs.6b09690

文献信息

• Pyrrolopyrimidine A2b selective antagonist compounds, their synthesis and use
  申请人：——

  公开号：US20030229067A1

  公开（公告）日：2003-12-11

  The subject invention provides compounds having the structure: 1 wherein, R 1 is a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NR a R b , —NR a R b , —NR a C(═O)NR a R b , —NR a C(═O)OR a , —OC(═O)NR a R b , or —NHC(═O)R a ; R 2 is hydrogen or a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NR a R b , —NR a R b , —NR a C(═O)NR a R b , —NR a C(═O)OR a , —OC(═O)NR a R b , or —NHC(═O)R a , or R 1 , R 2 and N together form a substituted piperazine, substituted azetidine ring, or a pyrrolidine ring substituted with —(CH 2 ) 2 OH or —CH 2 C(═O)OH; R 3 is a substituted or unsubstituted phenyl or a 5-6 membered heteroaryl ring, wherein the substituent is halogen, hydroxyl, cyano, (C 1 -C 15 )alkyl, (C 1 -C 15 )alkoxy, or —NR a R b ; R 4 is hydrogen or substituted or unsubstituted (C 1 -C 15 )alkyl; R 5 is —(CH 2 ) m OR 6 , —CHNOR 7 , —C(═O)NR 8 R 9 , —(CH 2 ) m C(═O)OR 10 , —(CH 2 ) k C(═O)NR 11 R 12 ; wherein R 6 is a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or 4-8 membered heterocyclic ring; R 7 is hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl; R 8 and R 9 are each independently hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylamino, (C 1 -C 30 )alkoxy, or a saturated or unsaturated, monocyclic or bicyclic, carbocyclic or heterocyclic ring, or R 8 , N, and R 9 together form a substituted or unsubstituted 4-8 membered heterocyclic ring; R 10 is hydrogen or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or heterocyclic ring; R 11 , N and R 12 together form a 4-8 membered heterocyclic ring; R a and R b are each independently hydrogen or alkyl; m is 0, 1, 2 or 3; and k is 1, 2 or 3, or a specific enantiomer thereof, or a specific tautomer thereof, or a pharmaceutically acceptable salt thereof, and a method for treating a disease associated with the A 2b adenosine receptor in a subject in need of such treatment comprising administering to the subject a therapeutically effective amount of the compounds of the invention.

  该主题发明提供具有以下结构的化合物： 1 其中， R 1 是取代或未取代的烷基，其中取代基是羟基、二羟基、羧基、—C(═O)NR a R b 、—NR a R b 、—NR a C(═O)NR a R b 、—NR a C(═O)OR a 、—OC(═O)NR a R b 或—NHC(═O)R a ； R 2 是氢或取代或未取代的烷基，其中取代基是羟基、二羟基、羧基、—C(═O)NR a R b 、—NR a R b 、—NR a C(═O)NR a R b 、—NR a C(═O)OR a 、—OC(═O)NR a R b 或—NHC(═O)R a ，或 R 1 、R 2 和N共同形成取代哌嗪、取代氮杂环丙烷环或取代的—(CH 2 ) 2 OH或—CH 2 C(═O)OH的吡咯烷环； R 3 是取代或未取代的苯基或5-6成员杂芳环，其中取代基是卤素、羟基、氰基、(C 1 -C 15 )烷基、(C 1 -C 15 )烷氧基或—NR a R b ； R 4 是氢或取代或未取代的(C 1 -C 15 )烷基； R 5 是—(CH 2 ) m OR 6 、—CHNOR 7 、—C(═O)NR 8 R 9 、—(CH 2 ) m C(═O)OR 10 、—(CH 2) k C(═O)NR 11 R 12 ； 其中R 6 是取代或未取代的(C 1 -C 30 )烷基、(C 3 -C 10 )环烷基或芳基、杂芳基或4-8成员杂环环； R 7 是氢或取代或未取代的(C 1 -C 30 )烷基、(C 1 -C 30 )烷基芳基； R 8 和R 9 各自独立地是氢或取代或未取代的(C 1 -C 30 )烷基、(C 1 -C 30 )烷基芳基、(C 1 -C 30 )烷基氨基、(C 1 -C 30 )烷氧基或饱和或不饱和的、单环或双环的、碳环或杂环环，或 R 8 、N和R 9 共同形成取代或未取代的4-8成员杂环环； R 10 是氢或取代或未取代的(C 1 -C 30 )烷基、(C 3 -C 10 )环烷基或芳基、杂芳基或杂环环； R 11 、N和R 12 共同形成4-8成员杂环环； R a 和R b 各自独立地是氢或烷基； m为0、1、2或3；和 k为1、2或3， 或其特定对映体，或其特定互变异构体，或其药学上可接受的盐，以及一种治疗与需要此类治疗的受试者相关的A 2b 腺苷受体相关疾病的方法，包括向受试者施用该发明化合物的治疗有效量。
• Asymmetric Michael Reactions on Polymeric Support: Auxiliary Immobilization and Stereoselective Construction of Quaternary Stereocenters
  作者：Burkard Kreidler、Angelika Baro、Jens Christoffers

  DOI：10.1002/ejoc.200500450

  日期：2005.12

  Merrifield resin and on poly(ethylene glycol) are reported. The latter is shown to work excellently in asymmetric copper(II)-catalyzed Michael reactions of cyclic β-oxo esters 2 with methyl vinyl ketone (4), yielding the corresponding addition products 5 with quaternary stereocenter in selectivities of 97–99 % ee. The PEG-supported auxiliary 1d can be precipitated from diethyl ether solutions and reused

  报道了将 L-缬氨酸衍生的辅助剂固定在 Merrifield 树脂和聚 (乙二醇) 上的几种策略。后者在不对称铜 (II) 催化的环状 β-氧代酯 2 与甲基乙烯基酮 (4) 的迈克尔反应中表现出色，以 97-99% ee 的选择性产生相应的加成产物 5，其具有季立体中心。PEG 支持的助剂 1d 可以从乙醚溶液中沉淀出来并重复使用。通过 DMAP 催化的酯交换方法以 92% 的产率制备含硫 β-氧代酯 2c，以检测固体载体上的烯胺形成。硫含量可用作燃烧分析中的附加参数，因此可用作烯胺形成的诊断探针。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
• Benzimidazole derivatives
  申请人：Merck, Sharp, & Dohme, Ltd.

  公开号：US05714498A1

  公开（公告）日：1998-02-03

  The invention is directed to substituted benzimidazole compounds which are ligands for dopamine receptor subtypes used in the treatment of the dopamine system.

  这项发明涉及替代苯并咪唑化合物，它们是多巴胺受体亚型的配体，用于治疗多巴胺系统。
• [EN] EHPATITIS B ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTIVIRAUX DE L'HÉPATITE B
  申请人：ENANTA PHARM INC

  公开号：WO2016183266A1

  公开（公告）日：2016-11-17

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: X-A-Y-Z-L-R1 (I) which inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV life cycle of the hepatitis B virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HBV infection. The invention also relates to methods of treating an HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明揭示了化合物(I)的公式，或其药学上可接受的盐、酯或前药：X-A-Y-Z-L-R1（I），其抑制由乙型肝炎病毒（HBV）编码的蛋白质或干扰HBV生命周期的功能，并且也可用作抗病毒剂。本发明还涉及包含上述化合物的制药组合物，用于治疗患有HBV感染的受试者。本发明还涉及通过给予包含本发明化合物的制药组合物来治疗受试者的HBV感染的方法。
• Azetidine, pyrrolidine and piperidine derivatives
  申请人：Merck Sharpe & Dohme Ltd.

  公开号：US05998440A1

  公开（公告）日：1999-12-07

  A class of substituted azetidine, pyrrolidine and piperidine derivatives, linked by a fluoro-substituted alkylene chain to a fused bicyclic heteroaromatic moiety such as indolyl, are selective agonists of 5-HT.sub.1 -like receptors, being potent agonists of the human 5-HT.sub.1D.alpha. receptor subtype while possessing at least a 10-fold selective affinity for the 5-HT.sub.1D.alpha. receptor subtype relative to the 5-HT.sub.1D.beta. subtype; they are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT.sub.1D receptors is indicated, while eliciting fewer side-effects, notably adverse cardiovascular events, than those associated with non-subtype-selective 5-HT.sub.1D receptor agonists.

  一类取代的氮杂环衍生物，包括氮杂丙烷、吡咯烷和哌嗪衍生物，通过含氟取代的烷基链连接到融合的双环杂芳基部分，例如吲哚基，它们是5-HT.sub.1-样受体的选择性激动剂，是人类5-HT.sub.1Dα受体亚型的有效激动剂，同时相对于5-HT.sub.1Dβ亚型具有至少10倍的选择性亲和力；因此，它们在治疗和/或预防临床病症方面具有用途，特别是偏头痛和相关疾病，需要亚型选择性的5-HT.sub.1D受体激动剂，同时引起的副作用较少，尤其是不良心血管事件，相对于非亚型选择性的5-HT.sub.1D受体激动剂。