4-哌啶酮缩乙二醇 | 177-11-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 4-哌啶酮缩乙二醇
• 中文别名: 4-哌啶酮乙烯缩酮；1,4-二叠氮-8-壬烯；4-哌啶乙烯缩酮
• 英文名称: 4,4-ethylenedioxy-piperidine
• 英文别名: 1,4-dioxa-8-azaspiro[4.5]decane；4-piperidone ethylene acetal；4-piperidinone ethylene acetal；4-piperidone ethylene ketal；8-aza-1,4-dioxaspiro[4.5]decane
• CAS: 177-11-7
• 化学式: C₇H₁₃NO₂
• mdl: MFCD00005976
• 分子量: 143.186
• InChiKey: KPKNTUUIEVXMOH-UHFFFAOYSA-N

物化性质

• 沸点：
  108-111 °C26 mm Hg(lit.)
• 密度：
  1.117 g/mL at 20 °C(lit.)
• 闪点：
  179 °F
• 溶解度：
  可溶于DCM、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25,S26,S36
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 储存条件：
  存放于惰性气体中；避免接触湿气（否则可能分解）。

SDS

Name:	1 4-Dioxa-8-azaspiro(4.5)decane 98% Material Safety Data Sheet
Synonym:	4-Piperidone ethylene keta
CAS:	177-11-7

Section 1 - Chemical Product MSDS Name:1 4-Dioxa-8-azaspiro(4.5)decane 98% Material Safety Data Sheet
Synonym:4-Piperidone ethylene keta

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
177-11-7	1,4-Dioxa-8-azaspiro[4.5]decane	98	205-868-6

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin irritation. May cause dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Aspiration may lead to pulmonary edema. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Combustible liquid.
Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust. Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 177-11-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Clear liquid
Color: colorless to yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 108.0 - 110.0 deg C @ 26.00mm
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 81 deg C ( 177.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: 1.1170g/cm3
Molecular Formula: C7H13NO2
Molecular Weight: 143.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 177-11-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,4-Dioxa-8-azaspiro[4.5]decane - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 177-11-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 177-11-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 177-11-7 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

4-哌啶酮缩乙二醇可应用于合成稠合嘧啶哌啶环衍生物，并且也能够合成具有良好FXR激动活性的化合物。

反应信息

• 作为反应物：
  描述：

  4-哌啶酮缩乙二醇 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 甲酸 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 1-(4-甲基苯)哌啶-4-酮
  参考文献：
  名称：

  [EN] NOVEL TETRAHYDROPYRIDOPYRIMIDINES AND TETRAHYDROPYRIDOPYRIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
  [FR] NOUVELLES TÉTRAHYDROPYRIDOPYRIMIDINES ET TÉTRAHYDROPYRIDOPYRIDINES POUR LE TRAITEMENT ET LA PRÉVENTION D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B

  摘要：

  这项发明提供了具有一般式（I）的新化合物：其中R1、R2、R3、Q、U、W、Z、X和Y如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。这些化合物是HbsAg抑制剂，可用作治疗或预防HBV感染的药物。

  公开号：

  WO2016107832A1
• 作为产物：
  描述：

  4-羟基-1-哌啶甲酸苄酯 在 palladium on activated charcoal 氢气 、 三氧化硫吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 121.0h， 生成 4-哌啶酮缩乙二醇
  参考文献：
  名称：

  Cooper, Curt S.; Klock, Pamela L.; Chu, Daniel T. W., Journal of Medicinal Chemistry, 1992, vol. 35, # 8, p. 1393 - 1398

  摘要：

  DOI：
• 作为试剂：
  描述：

  1,1-二苯乙烯 、 环己烷 、 一氧化碳 在 二叔丁基过氧化物 、 4-哌啶酮缩乙二醇 作用下， 130.0 ℃ 、6.0 MPa 条件下， 反应 10.0h， 以14%的产率得到1-cyclohexyl-3,3-diphenylprop-2-en-1-one
  参考文献：
  名称：

  碳纳米纤维微球促进烷烃与CO的氧化双羰基化

  摘要：

  在这里，已成功实现了O和N掺杂的碳纳米纤维双微球（CNM）促进烷烃与CO的化学转化。散装化学品的有效转化在化学合成中具有重要意义。涉及CO的羰基化是在工业界和学术界中构造羰基化合物的重要过程，其中金属催化的羰基化尤为突出。但是，CO的强配位能力和还原性通常会降低金属催化剂的活性。因此，迫切需要探索新颖的转化策略，例如制造新的材料来代替传统的催化剂。在这项工作中，我们表明，几丁质衍生的CNM介导烷烃的氧化双羰基化，以制备各种烷基α-酮酰胺。在我们的发现中，具有较大表面积的多孔CNM可以为胺提供潜在的粘附位点，从而抑制了胺的氧化分解，从而促进了这种转变。值得注意的是，据我们所知，烷烃C（sp3）–尚未报告H键。

  DOI：

  10.1016/j.chempr.2018.09.003

文献信息

• [EN] S-NITROSOMERCAPTO COMPOUNDS AND RELATED DERIVATIVES<br/>[FR] COMPOSÉS DE S-NITROSOMERCAPTO ET DÉRIVÉS APPARENTÉS
  申请人：GALLEON PHARMACEUTICALS INC

  公开号：WO2009151744A1

  公开（公告）日：2009-12-17

  The present invention is directed to mercapto-based and S- nitrosomercapto-based SNO compounds and their derivatives, and their use in treating a lack of normal breathing control, including the treatment of apnea and hypoventilation associated with sleep, obesity, certain medicines and other medical conditions.

  本发明涉及基于巯基和S-亚硝基巯基的SNO化合物及其衍生物，以及它们在治疗正常呼吸控制缺失方面的用途，包括治疗与睡眠、肥胖、某些药物和其他医疗状况相关的呼吸暂停和低通气。
• Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds
  申请人：Abbott Laboratories

  公开号：US20040116518A1

  公开（公告）日：2004-06-17

  The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases and cerebral vasospasm, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及新型肉桂酰胺化合物，用于治疗炎症和免疫性疾病以及脑血管痉挛，以及含有这些化合物的药物组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• [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。
• Inhibitors of histone deacetylase
  申请人：——

  公开号：US20020177594A1

  公开（公告）日：2002-11-28

  Compounds having the formula 1 or therapeutically acceptable salts thereof, are histone deacetylase (HDAC) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed.

  具有以下化学式的化合物或其治疗上可接受的盐是组蛋白去乙酰化酶（HDAC）抑制剂。本文揭示了该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法。
• Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design
  作者：Nathan J. Adamson、Haleh Jeddi、Steven J. Malcolmson

  DOI：10.1021/jacs.9b02637

  日期：2019.5.29

  surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.

  在这项研究中，我们确定共轭烯炔在 Pd 催化下进行选择性 1,4-加氢胺化，以提供带有侧链烯丙基胺的手性丙二烯。在非对映选择性反应中，DPEphos 作为 Pd 的配体，几种伯胺和仲脂肪胺和芳基取代的胺与各种单取代和双取代的烯炔偶联。二苯甲酮亚胺作为氨替代物，在两步/一锅法中提供伯胺。手性催化剂的检查揭示了 CN 键形成的高度可逆性，这对对映选择性产生了负面影响。因此，开发了一种缺电子的二茂铁基-PHOX 配体，以实现高效和对映选择性的烯炔加氢胺化。

表征谱图