(R)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine | 60419-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine
• 英文别名: (R)-(-)-1-(2-pyrrolidinylmethyl)pyrrolidine；(R)-2-((pyrrolidin-1-yl)methyl)pyrrolidine；(R)-2-[(pyrrolidin-1-yl)methyl]pyrrolidine；(2R)-1-(pyrrolidin-2-ylmethyl)pyrrolidine；(R)-1-(pyrrolidin-2-ylmethyl)pyrrolidine；1-[[(2R)-pyrrolidin-2-yl]methyl]pyrrolidine
• CAS: 60419-23-0
• 化学式: C₉H₁₈N₂
• mdl: MFCD00013441
• 分子量: 154.255
• InChiKey: YLBWRMSQRFEIEB-SECBINFHSA-N

物化性质

• 沸点：
  265.8±0.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H227,H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: (R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine

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: (R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine
Percent: >98.0%(GC)(T)
60419-23-0
CAS Number:
Chemical Formula: C9H18N2
(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine

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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.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
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
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
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
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
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
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
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
Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Storage conditions:
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Comply with laws.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine

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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 - Slightly pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
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):
(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine

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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：

  (R)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine 在 aluminium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (R)-(+)-1-<2-(3,4-dichlorophenyl)ethyl>-2-(1-pyrrolidinylmethyl)pyrrolidine
  参考文献：
  名称：

  构象受限的2-（1-吡咯烷基）-N- [2-（3,4-二氯苯基）乙基] -N-甲基亚乙基二烯的合成和生物学评估。1.吡咯烷，哌啶，高哌啶和四氢异喹啉类。

  摘要：

  描述了一系列2-（1-吡咯烷基）-N- [2-（3,4-二氯苯基）乙基] -N-甲基乙二胺（1）的构象受限衍生物的合成和sigma受体亲和力。该sigma受体药效基团的吡咯烷基（或N，N-二烷基），乙二胺，N-烷基和苯乙基部分受其并入1,2-环己烷二胺-，吡咯烷-，哌啶-，高哌啶-和四氢异喹啉-的限制。含有配体。使用[3H]（+）-喷他佐辛在豚鼠脑匀浆中测定这些化合物的sigma受体结合亲和力。除一类外，所有的合成都通过适当的二胺前体的酰化和烷烃还原来实现，该二胺前体的合成也已有报道。sigma受体亲和力范围为1.34 nM（对于6）（1R，2R）-反-N- [2-（3,4-二氯苯基）乙基] -N-甲基的7-二氯-2- [2-（1-（吡咯烷基）乙基]四氢异喹啉（12）至455 nM -2-（1-吡咯烷基）环己胺[（-）-4]。在该置换试验中，（+）-戊唑嗪的Ki值为3.1 nM，而DTG和氟哌啶醇的Ki值分别为27

  DOI：

  10.1021/jm00101a011
• 作为产物：
  描述：

  D-焦谷氨酸 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 16.17h， 生成 (R)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

  摘要：

  Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N- methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00579-7
• 作为试剂：
  描述：

  2-乙酰基苯甲醛 、 环戊二烯 在 溶剂黄146 、 (R)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以88%的产率得到
  参考文献：
  名称：

  对映体合成6,6-二取代的五氟甲酸酯类，含手性侧链羟基

  摘要：

  使用市售的脯氨酸基有机催化剂，通过级联反应，可以轻松合成带有手性侧链羟基的6,6-二取代的五烯丙基戊烯的简单对映选择性合成。缩合环戊二烯与1,2-甲酰基苯乙酮的乙酰基官能团，然后环化生成的带有甲酰基的富烯稳定的碳负离子，生成双环手性醇，其er初始值高达94：6。结晶后会得到异常丰富的醇对映体富集-即使是外消旋的样品也会自发消旋。这使得能够快速获得对映体和非对映体纯的新的取代的环戊二烯家族。

  DOI：

  10.1002/chem.201704247

文献信息

• Chirality Transfer in Gold(I)-Catalysed Hydroalkoxylation of 1,3-Disubstituted Allenes
  作者：Stacey Webster、Daniel R. Sutherland、Ai-Lan Lee

  DOI：10.1002/chem.201603918

  日期：2016.12.19

  Gold(I)-catalysed intermolecular hydroalkoxylation of enantioenriched 1,3-disubstituted allenes was previously reported to occur with poor chirality transfer due to rapid allene racemisation. The first intermolecular hydroalkoxylation of allenes with efficient chirality transfer is reported here, exploiting conditions that suppress allene racemisation. A full substrate scope study reveals that excellent

  先前报道了金（I）催化的对映体富集的1，3-二取代的烯的分子间氢烷氧基化，由于快速的烯被外消旋作用，具有较差的手性转移。利用有效抑制手性外消旋作用的条件，本文报道了具有有效手性转移的丙二烯的第一个分子间加氢烷氧基化反应。全面的底物范围研究表明，当存在一个σ吸收性取代基时，可以实现出色的区域选择性和立体选择性。
• BENZOXAZEPIN COMPOUNDS SELECTIVE FOR PI3K P110 DELTA AND METHODS OF USE
  申请人：Heffron Timothy

  公开号：US20120245144A1

  公开（公告）日：2012-09-27

  Benzoxazepin Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  本句翻译为中文是：苯并恶唑啉I型化合物，包括立体异构体、几何异构体、互变异构体、代谢物以及药学上可接受的盐，对于抑制PI3K的δ异构体以及治疗由脂质激酶介导的疾病如炎症、免疫疾病和癌症是有用的。公开了使用I型化合物公式进行体外、原位和体内诊断、预防或治疗哺乳动物细胞中此类疾病或相关病理状况的方法。
• Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors
  申请人：Cui Jean Jingrong

  公开号：US20060046991A1

  公开（公告）日：2006-03-02

  Enantiomerically pure compound of formula 1 are provided, as well as methods for their synthesis and use. Preferred compounds are potent inhibitors of the c-Met protein kinase, and are useful in the treatment of abnormal cell growth disorders, such as cancers.

  提供了式1的对映纯化合物，以及它们的合成和使用方法。优选化合物是c-Met蛋白激酶的强效抑制剂，并且在治疗异常细胞生长紊乱，如癌症方面具有用处。
• Hexahydro-cyclohepta-pyrrole oxindole as potent kinase inhibitors
  申请人：SUGEN, Inc.

  公开号：US20040186160A1

  公开（公告）日：2004-09-23

  The present invention is directed to a class indolinone compounds, hexahydro-cyclohepta-pyrrole oxindoles, which are useful as protein kinase inhibitors.

  本发明涉及一类吲哚酮化合物，即六氢-环庚-吡咯酮氧吲哚，其作为蛋白激酶抑制剂具有用途。
• Treatment of acute myeloid leukemia with indolinone compounds
  申请人：SUGEN, Inc.

  公开号：US20030130280A1

  公开（公告）日：2003-07-10

  A method of treating acute myeloid leukemia in patient positive for FLT-3-ITD is described. The treatment is accomplished by administration of a compound of Formula I or II as defined herein.

  描述了一种治疗FLT-3-ITD阳性患者急性髓系白血病的方法。该治疗通过给予本文中定义的I或II式化合物来实现。