4-甲酰基-N-CBZ 哌啶 | 138163-08-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲酰基-N-CBZ 哌啶
• 中文别名: 4-甲酰基-N-CBZ哌啶；1-N-Cbz-4-甲酰基哌啶；4-甲酰基哌啶-1-甲酸苄酯；1-CBZ-4-哌啶甲醛；4-甲酰基-N-Cbz-哌啶；1-Cbz-4-哌啶甲醛；1-N-CBZ-4-甲酰基哌啶；N-CBZ-4-哌啶甲醛
• 英文名称: N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde
• 英文别名: 1-benzyloxycarbonyl-4-piperidinecarbaldehyde；benzyl 4-formylpiperidine-1-carboxylate；4-formyl-N-CBZ-piperidine；4-formylpiperidine-1-carboxylic acid benzyl ester
• CAS: 138163-08-3
• 化学式: C₁₄H₁₇NO₃
• mdl: MFCD01317806
• 分子量: 247.294
• InChiKey: ZJQMLJFHCKTCSF-UHFFFAOYSA-N

物化性质

• 沸点：
  384.5±42.0 °C(Predicted)
• 密度：
  1.22g/ml

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 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
• 储存条件：
  室温

SDS

Name:	Benzyl 4-formyltetrahydro-1(2H)-pyridinecarboxylate 90+% Material Safety Data Sheet
Synonym:	4-Formyl-piperidine-1-carboxylic acid benzyl este
CAS:	138163-08-3

Section 1 - Chemical Product MSDS Name:Benzyl 4-formyltetrahydro-1(2H)-pyridinecarboxylate 90+% Material Safety Data Sheet
Synonym:4-Formyl-piperidine-1-carboxylic acid benzyl este

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
138163-08-3	Benzyl 4-formyltetrahydro-1(2H)-pyridi	90+%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 138163-08-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Viscous liquid
Color: yellow
Odor: sweetish odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H17NO3
Molecular Weight: 247

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, amines, reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 138163-08-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Benzyl 4-formyltetrahydro-1(2H)-pyridinecarboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 138163-08-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 138163-08-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 138163-08-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

4-甲酰基-N-CBZ 哌啶在常温常压下为液体状，是一种哌啶类衍生物，主要用于有机合成和生物化学合成中间体。它还可用于药物分子及生物活性分子的衍生化。

合成方法

将草酰氯（59.1毫升，674毫摩尔）溶解在二氯甲烷（500毫升）中，并冷却至-78℃。随后加入二甲亚砜（68.3毫升，963毫摩尔），搅拌15分钟后，再加入4-羟甲基哌啶-1-羧酸苄酯（2，120克，481毫摩尔）溶解在二氯甲烷（500毫升）中的溶液。将此混合物升温至-55℃，继续搅拌反应15分钟后再冷却至-78℃。然后加入三乙胺（205毫升，1443毫摩尔），溶解于二氯甲烷（250毫升）中。使悬浮液升至室温，并用冰醋酸（100毫升）淬灭。接下来用水洗涤溶液，水相再用二氯甲烷（2×200毫升）萃取，合并的有机层经盐水洗涤后在硫酸钠上干燥并过滤除去干燥剂，最后浓缩得到4-甲酰基哌啶-1-羧酸苄酯（119克，收率100%）。

图 4-甲酰基-N-CBZ 哌啶的合成路线

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  N-Cbz-哌啶-4-羧酸	1-benzyloxycarbonylpiperidine-4-carboxylic acid	10314-98-4	C14H17NO4	263.293
  4-氯羰酰四氢-吡啶羧酸苄酯	benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate	10314-99-5	C14H16ClNO3	281.739
  1-Cbz-4-羟甲基哌啶	benzyl 4-(hydroxymethyl)piperidine-N-carboxylate	122860-33-7	C14H19NO3	249.31
  1-Cbz-4-哌啶甲酸甲酯	methyl-1-benzyloxycarbonyl-4-piperidinecarboxylate	138163-07-2	C15H19NO4	277.32
  1-Cbz-哌啶-4-甲酸乙酯	1-benzyl 4-ethyl piperidine-1,4-dicarboxylate	160809-38-1	C16H21NO4	291.347
  1-Cbz-n-甲氧基-n-甲基-4-哌啶羧酰胺	benzyl 4-{[methoxy(methyl)amino]carbonyl}piperidine-1-carboxylate	148148-48-5	C16H22N2O4	306.362
  1-叔丁氧羰基哌啶-4-甲醛	tert butyl 4-formylpiperidine-1-carboxylate	137076-22-3	C11H19NO3	213.277

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1-Cbz-4-羟甲基哌啶	benzyl 4-(hydroxymethyl)piperidine-N-carboxylate	122860-33-7	C14H19NO3	249.31
  ——	benzyl 4-vinylpiperidine-1-carboxylate	138163-09-4	C15H19NO2	245.321
  1-N-Cbz-4-氰基哌啶	benzyl 4-cyanopiperidine-1-carboxylate	161609-84-3	C14H16N2O2	244.293
  ——	benzyl 4-(difluoromethyl)piperidine-1-carboxylate	1624605-95-3	C14H17F2NO2	269.291
  N-苄氧羰基-4-哌啶丙酸	3-(N-benzyloxycarbonyl-4-piperidyl)propionoic acid	63845-33-0	C16H21NO4	291.347
  ——	(RS)-1-Benzyloxycarbonyl-4-(1-hydroxyethyl)piperidine	160809-35-8	C15H21NO3	263.337
  ——	4-Cyclopropylaminomethyl-piperidine-1-carboxylic acid benzyl ester	877858-53-2	C17H24N2O2	288.4
  1-Cbz-4-哌啶酮	benzyl 4-oxo-1-piperidinecarboxylate	19099-93-5	C13H15NO3	233.267
  N-Cbz-9-氧代-3-氮杂螺[5.5]十一烷	benzyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate	1056629-20-9	C18H23NO3	301.386
  ——	benzyl 4-(dimethoxymethyl)piperidine-1-carboxylate	——	C16H23NO4	293.363

反应信息

• 作为反应物：
  描述：

  4-甲酰基-N-CBZ 哌啶 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 螺[吲哚啉-3,4’-哌啶]-1’-羧酸苄酯
  参考文献：
  名称：

  基于螺吲哚啉的生长激素促分泌素MK-677的简便合成

  摘要：

  摘要描述了一种合成基于口服活性螺环二氢吲哚的生长激素促分泌素MK-677的简便方法。关键步骤采用了菲舍尔吲哚/还原策略。还优化了关键中间体N-保护的哌啶羧醛5和N-Boc-O-苄基-d-丝氨酸（2）的制备。

  DOI：

  10.1016/j.cclet.2012.03.032
• 作为产物：
  描述：

  1-Cbz-4-哌啶甲酸甲酯 在 二异丁基氢化铝 、 甲醇 、 水 、 sodium chloride 作用下， 以 甲苯 为溶剂， 以49%的产率得到4-甲酰基-N-CBZ 哌啶
  参考文献：
  名称：

  Substituted Spiro-amide Compounds

  摘要：

  将与式I相对应的螺环酰胺化合物替代为R5至R8、D、X、Y和Z具有定义含义的过程，用于制备这种螺环酰胺化合物，含有这种化合物的药物组合物，以及使用这种螺环酰胺化合物治疗和/或抑制至少部分由激肽酶1受体介导的疾病或疾病状态的方法。

  公开号：

  US20100249095A1
• 作为试剂：
  描述：

  (2-氧代-2-苯乙基)膦酸二乙酯 以 四氢呋喃 、 4-甲酰基-N-CBZ 哌啶 为溶剂， 生成 1-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylprop-1-en-1-yl)piperidine
  参考文献：
  名称：

  Pyrrolidine modulators of chemokine receptor activity

  摘要：

  本发明涉及式1的吡咯烷化合物：（其中R1、R2、R3、R4、R5、R6和n在此处定义），这些化合物可用作趋化因子受体活性的调节剂。具体来说，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。

  公开号：

  US06265434B1

文献信息

• Substituted Indole Compounds
  申请人：Schunk Stefan

  公开号：US20100222324A1

  公开（公告）日：2010-09-02

  Substituted indole compounds corresponding to the formula I: In which R 8 , R 9a , R 9b , R 10 , R 11 , R 200 , R 210 , A, D, T, q, s and t have defined meanings, processes for the preparation thereof, pharmaceutical compositions containing such compounds and the use of substituted indole compounds for the treatment or inhibition of pain and other conditions which are at least partly mediated by Bradykinin 1 receptors (B1R).

  将与下式I对应的吲哚化合物替代： 其中R8、R9a、R9b、R10、R11、R200、R210、A、D、T、q、s和t具有定义的含义，其制备方法，含有这种化合物的药物组合物以及用于治疗或抑制至少部分由Bradykinin 1受体（B1R）介导的疼痛和其他病症的替代吲哚化合物的用途。
• [EN] POLYCYCLIC COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF RAPIDLY ACCELERATED FIBROSARCOMA POLYPEPTIDES<br/>[FR] COMPOSÉS POLYCYCLIQUES ET MÉTHODES POUR LA DÉGRADATION CIBLÉE DE POLYPEPTIDES DU FIBROSARCOME RAPIDEMENT ACCÉLÉRÉ
  申请人：ARVINAS OPERATIONS INC

  公开号：WO2020051564A1

  公开（公告）日：2020-03-12

  The present disclosure relates to bifunctional compounds, ULM— L—PTM, which find utility as modulators of Rapidly Accelerated Fibrosarcoma (RAF, such as c-RAF, A- RAF and/or B-RAF; the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein RAF, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein, or the constitutive activation of the target protein, are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物ULM—L—PTM，其作为快速加速纤维肉瘤（RAF，如c-RAF、A-RAF和/或B-RAF；目标蛋白）的调节剂具有实用性。具体而言，本公开涉及含有一端结合到相应E3泛素连接酶的Von Hippel-Lindau、cereblon、凋亡抑制蛋白或鼠双分子同源物2配体的双功能化合物，另一端结合到目标蛋白RAF的部分，使得目标蛋白与泛素连接酶靠近，以实现目标蛋白的降解（和抑制）。本公开展示了与目标蛋白的降解/抑制相关的广泛药理活性范围。本公开的化合物和组合物用于治疗或预防由目标蛋白的聚集或积累，或目标蛋白的构成性激活导致的疾病或紊乱。
• [EN] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES AS HISTAMINE H3 ANTAGONISTS<br/>[FR] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR H3 DE L'HISTAMINE
  申请人：SCHERING CORP

  公开号：WO2003103669A1

  公开（公告）日：2003-12-18

  Disclosed are histamine H3 antagonists of the formula (I) wherein R1 is benzimidazolone derivative, M1 and M2 are optionally substituted carbon or nitrogen, R2 includes optionally substituted aryl or heteroaryl, and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of Formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of formula (I) in combination with a H1 receptor antagonist.

  揭示了公式（I）中的组胺H3拮抗剂，其中R1是苯并咪唑酮衍生物，M1和M2是可选择地取代的碳或氮，R2包括可选择地取代的芳基或杂环基，其余变量如规范中所定义。还揭示了包括公式（I）化合物的药物组合物。还揭示了使用公式（I）化合物治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）的方法。还揭示了使用公式（I）化合物与H1受体拮抗剂结合治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）。
• N-substituted nonaryl-heterocyclic NMDA/NR2B antagonists
  申请人：——

  公开号：US20020165241A1

  公开（公告）日：2002-11-07

  Compounds represented by Formula (I): 1 or pharmaceutically acceptable salts thereof, are effective as NMDA NR2B antagonists useful for relieving pain.

  由化学式（I）表示的化合物及其药学上可接受的盐，可作为NMDA NR2B拮抗剂，用于缓解疼痛。
• Substituted Disulfonamide Compounds
  申请人：REICH Melanie

  公开号：US20100152158A1

  公开（公告）日：2010-06-17

  Substituted disulfonamide compounds corresponding to formula I: In which R 1 , R 2 , R 3 , R 4a , R 4b , R 5a , R 5b , R 8 , R 9a , R 9b , R 10 , R 11 , a, b, s, t and A have defined meanings, pharmaceutical compositions containing one or more such compounds, processes for preparing such compounds, and a method of using such compounds for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin receptor 1 (BR1).

  将对应于公式I的取代二磺酰胺化合物： 其中R 1 ，R 2 ，R 3 ，R 4a ，R 4b ，R 5a ，R 5b ，R 8 ，R 9a ，R 9b ，R 10 ，R 11 ，a，b，s，t和A具有定义的含义，包含一种或多种此类化合物的药物组合物，制备这种化合物的方法，以及使用这种化合物治疗或抑制由激肽酶受体1（BR1）介导的疼痛和/或其他病症的方法。