4-氰基-4-羟基哌啶-1-羧酸叔丁酯 | 908140-15-8

• 物质功能分类: 医药中间体 - 杂环化合物
• 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-氰基-4-羟基哌啶-1-羧酸叔丁酯
• 英文名称: tert-butyl 4-cyano-4-hydroxypiperidine-1-carboxylate
• 英文别名: 1-Boc-4-cyano-4-hydroxypiperidine
• CAS: 908140-15-8
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: WWAGFFFOCPKWFA-UHFFFAOYSA-N

物化性质

• 沸点：
  370.1±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存储条件：2-8°C，干燥且密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 4-cyano-4-hydroxypiperidine-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-cyano-4-hydroxypiperidine-1-carboxylate
CAS number: 908140-15-8

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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.
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: C11H18N2O3
Molecular weight: 226.3

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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：

  4-氰基-4-羟基哌啶-1-羧酸叔丁酯 在 lithium aluminium tetrahydride 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 2,2,2-三氟乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.5h， 生成
  参考文献：
  名称：

  定制SnAP试剂，用于合成C取代的螺环和双环饱和N-杂环

  摘要：

  通过将醛与新型SnAP试剂结合使用，可轻松实现C取代基在双环和螺环N杂环上的精确定位。取代的SnAP试剂易于从简单的起始原料制备，并在室温下，在操作简单的条件下与多种芳香族和杂芳香族醛类偶联，以递送取代的吗啉和哌嗪产品。

  DOI：

  10.1021/acs.orglett.5b00618
• 作为产物：
  描述：

  氰化钠 、 N-叔丁氧羰基-4-哌啶酮 在 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 生成 4-氰基-4-羟基哌啶-1-羧酸叔丁酯
  参考文献：
  名称：

  Oxyindole derivatives

  摘要：

  这项发明涉及以下式（I）的化合物： 或其药学上可接受的盐，其中： A，R1，R2，R3，R4和R5分别如本文所述或药学上可接受的盐，以及含有这种化合物的组合物和利用这种化合物治疗由5-HT 4 激动活性介导的疾病的用途，例如但不限于胃食管反流病、胃肠疾病、胃动力障碍、非溃疡性消化不良、功能性消化不良、肠易激综合征（IBS）、便秘、消化不良、食管炎、胃食管疾病、恶心、中枢神经系统疾病、阿尔茨海默病、认知障碍、呕吐、偏头痛、神经系统疾病、疼痛、心血管疾病、心力衰竭、心律失常、糖尿病或呼吸暂停综合征。

  公开号：

  US20060194842A1

文献信息

• Photoredox-Catalyzed C_α–H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies
  作者：Ozgur Yilmaz、Martins S. Oderinde、Marion H. Emmert

  DOI：10.1021/acs.joc.8b01700

  日期：2018.9.21

  general, high-yielding amine Cα–H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient Cα–H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology

  本文描述了开发和一个一般地，高产胺的C机理研究α -H氰化经由photoredox催化协议。廉价的NaCN用作氰化物源，空气是外部氧化剂，导致温和且高度官能团耐受的条件。值得注意的是，高效的C α -H的cyanations二级和三级可使用所建立的方法进行脂族胺和复杂的，生物活性化合物（药物）的。机理研究表明，该羧酸添加剂具有三种作用：形成稳定的半胱氨酸中间体，通过使底物质子化来防止催化剂分解以及调节光激发催化剂物种的荧光猝灭。
• A single-step, mild, neutral, catalyst-free method for cyanohydrin synthesis
  作者：Mariam S. Degani、Manoj D. Kakwani、Nutan H. Palsule Desai、Ranjeet Bairwa

  DOI：10.1007/s00706-011-0613-4

  日期：2012.3

  carbonyl compounds can be transformed to their corresponding cyanohydrins in a single step using a dimethyl sulfoxide (DMSO)–water system in excellent yields (75–94%). The major advantages of this system are that the reaction conditions are mild and neutral; the reaction proceeds without catalyst and gives the corresponding cyanohydrins in short time (15–120 min). Graphical Abstract

  摘要使用二甲亚砜（DMSO）-水系统可将多种羰基化合物一步转化为相应的氰醇，收率很高（75-94％）。该系统的主要优点是反应条件温和，中性。反应在没有催化剂的情况下进行，并在短时间内（15-120分钟）产生了相应的氰醇。 图形概要
• [EN] CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES AS JANUS KINASE INHIBITORS<br/>[FR] CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES EN TANT QU'INHIBITEURS DE JANUS KINASE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013040863A1

  公开（公告）日：2013-03-28

  Cycloalkylnitrile pyrazole carboxamides as JAK inhibitors useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer are provided.

  提供环烷基腈吡唑羧酰胺作为JAK抑制剂，用于治疗JAK介导的疾病，如类风湿关节炎、哮喘、慢性阻塞性肺病和癌症。
• OXYINDOLE DERIVATIVES
  申请人：Uchida Chikara

  公开号：US20100173925A1

  公开（公告）日：2010-07-08

  This invention relates to compounds of the formula (I): or a pharmaceutically acceptable salt thereof, wherein: A, R 1 , R 2 , R 3 , R 4 and R 5 are each as described herein or a pharmaceutically acceptable salt, and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by 5 -HT 4 agonistic activity such as, but not limited to, as gastroesophageal reflux disease, gastrointestinal disease, gastric motility disorder, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome (IBS), constipation, dyspepsia, esophagitis, gastroesophageal disease, nausea, central nervous system disease, Alzheimer's disease, cognitive disorder, emesis, migraine, neurological disease, pain, cardiovascular disorders, cardiac failure, heart arrhythmia, diabetes or apnea syndrome.

  本发明涉及式(I)化合物或其药学上可接受的盐，其中： A，R1，R2，R3，R4和R5如本文所述或其药学上可接受的盐，以及含有这种化合物的组合物以及在治疗由5-HT4激动剂活性介导的病症中使用这种化合物，例如，但不限于，胃食管反流病、胃肠疾病、胃动力障碍、非溃疡性消化不良、功能性消化不良、肠易激综合征（IBS）、便秘、消化不良、食管炎、胃食管疾病、恶心、中枢神经系统疾病、阿尔茨海默病、认知障碍、呕吐、偏头痛、神经系统疾病、疼痛、心血管疾病、心力衰竭、心律失常、糖尿病或呼吸暂停综合征。
• ACYCLIC CYANOETHYLPYRAZOLES AS JANUS KINASE INHIBITORS
  申请人：Brubaker Jason

  公开号：US20140228358A1

  公开（公告）日：2014-08-14

  The instant invention provides compounds of formula I which are JAK inhibitors, and as such are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.

  本发明提供了I型化合物，它们是JAK抑制剂，因此可用于治疗JAK介导的疾病，如类风湿性关节炎、哮喘、慢性阻塞性肺疾病和癌症。