2-氧代哌啶-1-羧酸苄酯 | 106412-35-5

• 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: 2-氧代哌啶-1-羧酸苄酯
• 英文名称: N-benzyloxycarbonyl-2-piperidone
• 英文别名: benzyl 2-oxopiperidine-1-carboxylate
• CAS: 106412-35-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: LKGMGCSFOUSKCR-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±24.0 °C(Predicted)
• 密度：
  1.194 g/mL at 25 °C
• 闪点：
  >110℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8℃，干燥。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1-Z-2-Piperidone
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 106412-35-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
R52/53
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 1-N-(Benzyloxycarbonyl)-2-piperidone
Formula : C13H15NO3
Molecular Weight : 233,26 g/mol
CAS-No. : 106412-35-5
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
1-Z-2-Piperidone
CAS-No. 106412-35-5 <= 100 %

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point > 110 °C
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 1,1943 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,932
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
Harmful to aquatic life.

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氧代哌啶-1-羧酸苄酯 在 氯化二乙基铝 、 茴香硫醚 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.17h， 以97%的产率得到哌啶酮
  参考文献：
  名称：

  Efficient Detachment ofN-Benzyl Carbamate Group

  摘要：

  本文介绍了在温和条件下，结合使用硬路易斯酸和软亲核剂对氨基甲酸苄酯（N-Cbz）基团进行高效脱保护的过程。

  DOI：

  10.1055/s-2002-32986
• 作为产物：
  描述：

  哌啶酮 、 氯甲酸苄酯 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 2-氧代哌啶-1-羧酸苄酯
  参考文献：
  名称：

  氨基环丙烷的催化选择性环化：蛇毒精的正式合成和古霉素的全合成

  摘要：

  温和的控制：通过调节反应条件（参见方案），可实现氨基环丙烷在吲哚环的N1或C3位置的选择性环化。该策略适用于蛇毒精的正式合成和古霉素的总合成，对多种肿瘤细胞系均表现出显着的细胞毒性（IC 50 = 150–400 n M）。Cbz =苄氧羰基，Ts = 4-甲苯磺酰基

  DOI：

  10.1002/anie.201001853

文献信息

• Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes
  作者：Filippo De Simone、Tanguy Saget、Fides Benfatti、Sofia Almeida、Jérôme Waser

  DOI：10.1002/chem.201102583

  日期：2011.12.16

  Replacing one of the vinyl groups by a cyclopropane leads to a formal homo‐Nazarov process for the synthesis of cyclohexenones. In contrast to the Nazarov reaction, the cyclization of vinyl‐cyclopropyl ketones is a stepwise process, often requiring harsh conditions. Herein, we describe two different approaches for further polarization of the three‐membered ring of vinyl‐cyclopropyl ketones to allow the

  纳扎罗夫对二乙烯基酮的环化作用可得到环戊烯酮。用环丙烷取代乙烯基之一会导致形成正式的正己-纳扎罗夫合成环己烯酮的过程。与纳扎罗夫反应相反，乙烯基环丙基酮的环化是一个逐步过程，通常需要苛刻的条件。本文中，我们描述了两种不同的方法，可进一步极化乙烯基-环丙基酮的三元环，从而在温和的催化条件下进行正式的均一纳扎罗夫反应。在第一种方法中，将酯基α引入到环丙烷的羰基上，反应速率提高了十倍以上，这使我们可以将反应范围扩展到β位置的非电子富芳基供体取代基环丙烷上的羰基。在这种情况下，使用手性路易斯酸催化剂可以实现不对称诱导的原理证明。在第二种方法中，将杂原子（尤其是氮）引入β到环丙烷的羰基上。在这种情况下，当乙烯基被吲哚杂环取代时，反应特别成功。对于游离吲哚，使用铜催化剂观察到了吲哚C3位置的正式均一纳扎罗夫环化反应。相反，使用布朗斯台德酸催化剂观察到在N1位置发生了新的环化反应。两种反应均用于天然生物
• [EN] HETEROCYCLIC COMPOUND<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2019027054A1

  公开（公告）日：2019-02-07

  The present invention provides a heterocyclic compound having a HDAC inhibitory action, and useful for the treatment of central nervous system diseases including neurodegenerative disease, and the like, and a medicament comprising the compound. The present invention relates to a compound represented by the formula (I) wherein each symbol is as defined in the specification, or a salt thereof.

  本发明提供了一种具有HDAC抑制作用的杂环化合物，用于治疗包括神经退行性疾病在内的中枢神经系统疾病，以及包含该化合物的药物。本发明涉及一种由式(I)表示的化合物，其中每个符号如规范中定义的，或其盐。
• Unprecedented copper-catalyzed asymmetric conjugate addition of organometallic reagents to α,β-unsaturated lactams
  作者：Mauro Pineschi、Federica Del Moro、Francesca Gini、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1039/b403793f

  日期：——

  For the first time, an excellent enantioselectivity has been obtained in the conjugate addition of hard organometallic reagents to alpha,beta-unsaturated lactams bearing appropriate protecting-activating groups on the nitrogen.

  第一次，在将硬有机金属试剂共轭加到在氮上带有适当保护活化基团的α，β-不饱和内酰胺中，获得了极好的对映选择性。
• Efficient Synthesis of Piperidine Derivatives. Development of Metal Triflate-Catalyzed Diastereoselective Nucleophilic Substitution Reactions of 2-Methoxy- and 2-Acyloxypiperidines
  作者：Osamu Okitsu、Ritsu Suzuki、Shū Kobayashi

  DOI：10.1021/jo001297m

  日期：2001.2.1

  Nucleophilic substitution reactions of 2-methoxy- and 2-acyloxypiperidines were investigated. First, new and efficient methods for the preparation of the starting piperidine derivatives were developed. N-Benzyloxycarbonyl-2-methoxypiperidine (3) and 3-substituted-2-acyloxy-N-benzyloxycarbonylpiperidines (4a-d), which are recognized as the simplest imino-sugars, were prepared and were examined as substrates

  研究了2-甲氧基-和2-酰氧基哌啶的亲核取代反应。首先，开发了用于制备起始哌啶衍生物的新的有效方法。制备被认为是最简单的亚氨基糖的N-苄氧基羰基-2-甲氧基哌啶（3）和3-取代的-2-酰氧基-N-苄氧基羰基哌啶（4a-d）并作为亲核取代反应与甲硅烷基烯醇盐在催化量的金属三氟甲磺酸酯（Sc（OTf）3，Sn（OTf）2，Cu（OTf）2，Hf（OTf）4等）的影响下。在测试的三氟甲磺酸酯中，Sc（OTf）3给出了最佳结果。发现2-乙酰氧基-3-苄氧基-N-苄氧基羰基哌啶（4a）与烯丙基甲硅烷基酯反应得到高顺式选择性的2-烷基化加合物，而2，3-二酰氧基-N-苄氧基羰基哌啶（4b-d）显示出反选择性。使用NMR分析，X射线晶体学和合成转化过程仔细进行了立体化学分配。在这些非对映选择性亲核取代反应的基础上，由2,3-二乙酰氧基-N-苄氧基羰基哌啶（4b）成功合成了强效抗疟生物碱Febrifugine（1）。
• Asymmetric Construction of the Azaspiro[5.5]undec-8-ene System Towards Gymnodimine Synthesis
  作者：Takashi Tsujimoto、Jun Ishihara、Mariko Horie、Akio Murai

  DOI：10.1055/s-2002-20450

  日期：——

  In the course of the synthetic studies on gymnodimine, a potent shellfish toxin, the asymmetric construction of the azaspirocyclic part was achieved by the (-)-siam·Cu(SbF6)2 complex catalyzed intermolecular Diels-Alder reaction in high exo- and enantioselectivities.

  在对 Gymnodimine 这种强效贝类毒素的综合研究过程中，通过（-）-siam·Cu（SbF6）2 配合物催化的具有高外向选择性和对映选择性的分子间 Diels-Alder 反应，成功实现了氮杂螺环部分的不对称构建。