吡咯烷-2-甲醇 | 498-63-5

• 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 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 吡咯烷-2-甲醇
• 中文别名: 2-(羟甲基)吡咯烷；DL-脯氨醇；吡啶烷-2-甲醇
• 英文名称: 2-hydroxymethylpyrrolidine
• 英文别名: prolinol；pyrrolidin-2-ylmethanol
• CAS: 498-63-5
• 化学式: C₅H₁₁NO
• mdl: MFCD00601073
• 分子量: 101.148
• InChiKey: HVVNJUAVDAZWCB-UHFFFAOYSA-N

物化性质

• 沸点：
  98 °C / 14mmHg
• 密度：
  1.04
• 溶解度：
  溶于乙醇。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温下保存，并请密封。

SDS

DL-Prolinol Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: DL-Prolinol

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 4
Flammable liquids
HEALTH HAZARDS
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Combustible liquid
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Keep away from flames and hot surfaces.
[Prevention]
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.
[Storage] Store in a well-ventilated place. Keep cool.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: DL-Prolinol
Percent: >95.0%(GC)(T)
498-63-5
CAS Number:
Synonyms: 2-(Hydroxymethyl)pyrrolidine , 2-Pyrrolidinemethanol
DL-Prolinol

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Chemical Formula: C5H11NO

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Get medical advice/attention if you feel unwell. Rinse mouth.
Ingestion:
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water in large amounts, carbon dioxide.
Suitable extinguishing
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
case of a fire. Use spark-proof tools and explosion-proof equipment.
hazards:

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent generation of vapour or mist. Keep away from flames and hot surfaces. Take
measures to prevent the build up of electrostatic charge. Use explosion-proof
equipment. Wash hands and face thoroughly after handling.
Use a closed system, ventilation.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
DL-Prolinol

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Colour: Colorless - Yellow
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 76°C/0.3kPa
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 1.04
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Open flame
Conditions to avoid:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):
DL-Prolinol

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  吡咯烷-2-甲醇 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 tetrahydro-pyrrolo[1,2-c]thiazole-3-thione
  参考文献：
  名称：

  Evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2-imines as inhibitors of nitric oxide synthase

  摘要：

  Syntheses and evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2-imines as inhibitors of nitric oxide synthase (NOS) are discussed. An extensive SAR was established for pyrrolidin-2-imines class of compounds. The amidines came out as the most potent inhibitors in addition to displaying selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.033
• 作为产物：
  描述：

  DL-谷氨酸 在 磷酸 、 ruthenium-carbon composite 、 氢气 作用下， 以 水 为溶剂， 180.0 ℃ 、8.0 MPa 条件下， 反应 24.0h， 以36%的产率得到吡咯烷-2-甲醇
  参考文献：
  名称：

  アミノアルコール合成方法及び触媒

  摘要：

  【课题】提供一种能够以高收率合成氨基醇的氨基醇合成方法。【解决手段】该氨基醇合成方法包括以下步骤：在具有金属表面积50.0m²/g以上、粒径10.0nm以下的金属负载催化剂存在下，将氨基酸还原以生成氨基醇。【选择图】无。

  公开号：

  JP2017109940A
• 作为试剂：
  描述：

  3-甲基-2-丁酮 在 dimethyl sulfide borane 、 吡咯烷-2-甲醇 作用下， 以 四氢呋喃 为溶剂， 生成 (+)-3-甲基-2-丁醇 、 (R)-(-)-3-甲基-2-丁醇
  参考文献：
  名称：

  树枝状大分子担载脯氨醇的合成及其在酮的对映选择性还原中的应用

  摘要：

  合成了具有光学活性的树枝状氨基醇，并将其用于催化各种酮的对映选择性硼烷还原，具有良好的产率和高对映体过量。

  DOI：

  10.1055/s-2006-926253

文献信息

• Discovery and Development of <i>N</i>-[4-(1-Cyclobutylpiperidin-4-yloxy)phenyl]-2-(morpholin-4-yl)acetamide Dihydrochloride (SUVN-G3031): A Novel, Potent, Selective, and Orally Active Histamine H₃ Receptor Inverse Agonist with Robust Wake-Promoting Activity
  作者：Ramakrishna Nirogi、Anil Shinde、Abdul Rasheed Mohammed、Rajesh Kumar Badange、Veena Reballi、Thrinath Reddy Bandyala、Sangram Keshari Saraf、Kumar Bojja、Sravanthi Manchineella、Pramod Kumar Achanta、Kiran Kumar Kandukuri、Ramkumar Subramanian、Vijay Benade、Raghava Choudary Palacharla、Pradeep Jayarajan、Santoshkumar Pandey、Venkat Jasti

  DOI：10.1021/acs.jmedchem.8b01280

  日期：2019.2.14

  histamine H3 receptor (H3R), physicochemical properties, and pharmacokinetics in rats resulted in identification of N-[4-(1-cyclobutyl-piperidin-4-yloxy)phenyl]-2-(morpholin-4-yl)acetamide dihydrochloride (17v, SUVN-G3031) as a clinical candidate. Compound 17v is a potent (hH3R Ki = 8.73 nM) inverse agonist at H3R with selectivity over other 70 targets, Compound 17v has adequate oral exposures and

  在大鼠中对组胺H3受体（H3R）的体外亲和力，理化性质和药代动力学指导下的一系列化学优化导致鉴定了N- [4-（1-环丁基-哌啶丁-4-基氧基）苯基] -2 -（吗啉-4-基）乙酰胺二盐酸盐（17v，SUVN-G3031）作为临床候选药物。化合物17v在H3R上是一种强效（hH3R Ki = 8.73 nM）反向激动剂，对其他70个靶标具有选择性。化合物17v在大鼠和狗中均具有足够的口服暴露量和良好的消除半衰期。它显示出高的受体占有率和明显的促醒作用，并减少了Orexin-B萨泊林损伤的大鼠的快速眼动睡眠，支持了其在治疗人类睡眠障碍中的潜在治疗作用。剂量比有效剂量高出几倍，对运动活性没有影响。它没有hERG和磷脂病的问题。已经成功完成了对动物的安全性，耐受性和药代动力学的第一阶段评估，以及对动物的长期安全性研究，而无需担心进一步的开发。
• Src kinase inhibitor compounds
  申请人：Merck & Co., Inc.

  公开号：US06498165B1

  公开（公告）日：2002-12-24

  Pyrimidine compounds (Formula I), or their pharmaceutically acceptable salts, hydrates, solvates, crystal forms and individual diastereomers, and pharmaceutical compositions including the same, which are inhibitors of tyrosine kinase enzymes, and as such are useful in the prophylaxis and treatment of protein tyrosine kinase-associated disorders, such as immune diseases, hyperproliferative disorders and other diseases in which inappropriate protein kinase action is believed to play a role, such as cancer, angiogensis, atheroscelerosis, graft rejection, rheumatoid arthritis and psoriasis.

  嘧啶化合物（化学式I），或其药用可接受的盐、水合物、溶剂合物、晶型和单一对映异构体，以及包括这些化合物的药物组合物，它们是酪氨酸激酶酶的抑制剂，因此在预防和治疗蛋白酪氨酸激酶相关疾病方面具有用处，如免疫疾病、高增殖性疾病和其他认为不当的蛋白激酶作用可能起作用的疾病，如癌症、血管生成、动脉粥样硬化、移植排斥、类风湿性关节炎和牛皮癣。
• En Route to a Practical Primary Alcohol Deoxygenation
  作者：Xi-Jie Dai、Chao-Jun Li

  DOI：10.1021/jacs.6b02344

  日期：2016.4.27

  efficient mainly with activated alcohols, which dictates harsh reaction conditions and thus limits its synthetic utility. Later, a significant advancement has been made on aliphatic primary alcohol deoxygenation by employing a ruthenium complex, with good functional group tolerance and exclusive selectivity under practical reaction conditions. Its synthetic utility is further illustrated by excellent

  醇脱氧领域的一个长期科学挑战是在存在其他官能团（如广泛存在于生物分子中的游离羟基和胺）的情况下，具有高选择性和高效率的直接催化 sp(3) CO 去官能化。以前，选择性问题只能通过使用化学计量试剂的经典多步脱氧策略来解决。在此，我们提出了一种基于脱氢/沃尔夫-基什纳 (WK) 还原的催化后过渡金属催化氧化还原设计，以同时解决步骤经济性和选择性方面的挑战。我们假设的早期发展侧重于主要使用活化醇有效的铱催化过程，这决定了苛刻的反应条件，从而限制了其合成效用。之后，采用钌配合物在脂肪族伯醇脱氧方面取得了重大进展，在实际反应条件下具有良好的官能团耐受性和专属选择性。在简单和复杂的分子设置中，其卓越的效率以及完全的化学和区域选择性进一步说明了其合成效用。实验支持还包括机械讨论。总体而言，我们目前的方法成功地解决了相关领域中的上述挑战，为脂肪族伯醇的直接 sp(3) CO 去官能化提供了一种实用的基于
• FUSED MORPHOLINOPYRIMIDINES AND METHODS OF USE THEREOF
  申请人：FORUM Pharmaceuticals Inc.

  公开号：US20170044182A1

  公开（公告）日：2017-02-16

  The present disclosure relates to Fused Morpholinopyrimidines, pharmaceutical compositions comprising an effective amount of a Fused Morpholinopyrimidine and methods for using a Fused Morpholinopyrimidine in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a Fused Morpholinopyrimidine.

  本公开涉及融合吗啉吡嘧啶类化合物，包括有效量的融合吗啉吡嘧啶类化合物的药物组合物，以及在治疗神经退行性疾病中使用融合吗啉吡嘧啶类化合物的方法，包括向需要的受试者施用有效量的融合吗啉吡嘧啶类化合物。
• [EN] AZAINDAZOLES AS BTK KINASE MODULATORS AND USE THEREOF<br/>[FR] AZAINDAZOLES COMME MODULATEURS DE LA KINASE BTK ET LEUR UTILISATION
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011019780A1

  公开（公告）日：2011-02-17

  Compounds having the formula (I), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, (I) are useful as kinase modulators, including Btk modulation, wherein A1, A2, A3, R4, are as defined herein.

  具有化学式(I)的化合物，以及其对映体、非对映异构体、药用可接受的盐，(I)可用作激酶调节剂，包括Btk调节，在此处定义了A1、A2、A3、R4。

表征谱图