(S)-3-羟基吡咯烷盐酸盐 | 122536-94-1

• 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: (S)-3-羟基吡咯烷盐酸盐
• 中文别名: (S)-(+)-3-羟基吡咯烷盐酸盐；（S）-3-羟基吡咯烷盐酸盐；(S)-(-)-3-羟基吡咯烷盐酸盐；(S)-3-羟基吡咯烷盐酸盐L；(S)-3-羟基吡咯啉(HCL)；S-3-羟基吡咯盐酸盐；S-3-羟基吡咯烷盐酸盐
• 英文名称: (S)-3-hydroxypyrrolidine hydrochloride
• 英文别名: (S)-pyrrolidin-3-ol hydrochloride；(3S)-pyrrolidin-3-ol hydrochloride；(S)-3-pyrrolidinol hydrochloride；(S)-pyrrolidine-3-ol hydrochloride；(S)-pyrrolidin-3-ol hydrochloride salt；(S)-3-hydroxyl-pyrrolidine hydrochloride；(3S)-3-Hydroxypyrrolidine hydrochloride；(S)-3-hydroxypyrrolidine HCl salt；(3S)-pyrrolidin-3-ol;hydrochloride
• CAS: 122536-94-1
• 化学式: C₄H₉NO*ClH
• mdl: MFCD00272298
• 分子量: 123.582
• InChiKey: QPMSJEFZULFYTB-WCCKRBBISA-N

物化性质

• 熔点：
  104-107°C
• 沸点：
  108-110℃/8mm
• 溶解度：
  DMSO（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37
• 危险类别码：
  R,R36/37/38
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-Pyrrolidin-3-ol, HCl
Synonyms: (S)-(+)-3-Hydroxypyrrolidine hydrochloride

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: (S)-Pyrrolidin-3-ol, HCl
CAS number: 122536-94-1

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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.

---

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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H10ClNO
Molecular weight: 123.6

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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, hydrogen chloride.

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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

制备方法与用途

(S)-3-羟基吡咯烷盐酸盐可用作医药中间体，主要用于化工医药杂环设计过程中。

合成方法如下：取(3S)-N-苄基-3-羟基吡咯烷-2,5-二酮（100g），加入到1L高压反应釜中，再加入乙醇500mL和5g的10％钯碳催化剂（含水量58％，型号D10H5A，由陕西瑞科新材料股份有限公司提供）。通入氢气并保持反应体系压力在0.5MPa，然后慢慢升温至70℃，持续反应5小时。中控检查反应完成情况后，过滤回收钯碳，并浓缩溶剂。接着向残余物中加入200mL异丙醇搅拌溶解完全，随后滴加45mL浓度为12M的浓盐酸（过量1.1倍），在室温下搅拌过夜。最后，通过过滤得到白色固体产物，即(S)-3-吡咯烷醇盐酸盐，总收率为85％，纯度达到99.1％。

反应信息

• 作为反应物：
  描述：

  (S)-3-羟基吡咯烷盐酸盐 在 sodium hydroxide 、 sodium phosphate 作用下， 以 甲醇 为溶剂， 以88.7 %的产率得到(S)-3-吡咯烷醇
  参考文献：
  名称：

  WO2024121219A1

  摘要：

  公开号：
• 作为产物：
  描述：

  (3S)-N-苄基-3-羟基吡咯烷-2,5-二酮 在 palladium 10% on activated carbon 、 氢气 、 盐酸 作用下， 以 乙醇 、 异丙醇 为溶剂， 20.0~75.0 ℃ 、550.01 kPa 条件下， 反应 5.0h， 以88%的产率得到(S)-3-羟基吡咯烷盐酸盐
  参考文献：
  名称：

  一种(S)-3-吡咯烷醇盐酸盐的合成方法

  摘要：

  本发明公开了一种(S)‑3‑吡咯烷醇盐酸盐的合成方法，属于药物合成领域，该方法以L‑苹果酸与苄胺为原料经过脱水酰胺化得到(3S)‑N‑苄基‑3‑羟基吡咯烷‑2,5‑二酮，之后一锅法还原、脱苄基，成盐合成(S)‑3‑吡咯烷醇盐酸盐。本发明合成路线短，操作简单，收率高，产品纯度好，利于工业化生产。

  公开号：

  CN111518007B
• 作为试剂：
  描述：

  (S)-3-羟基吡咯烷盐酸盐 、 α-N-(ethoxycarbonyl)-D,L-phenylglycine 在 (S)-3-羟基吡咯烷盐酸盐 作用下， 生成 ethyl ((S)-2-((S)-3-hydroxypyrrolidin-1-yl)-2-oxo-1-phenylethyl)
  参考文献：
  名称：

  N-methyl-N-[(1S)-1-phenyl-2-(3S)-hydroxypyrrolidin-1-yl)ethyl]-2

  摘要：

  本发明涉及一种新的热稳定形式的N-甲基-N-[(1S)-1-苯基-2-((3S)-3-羟基吡咯烷-1-基)乙基]-2,2-二苯乙酰胺，以及制备和分离该化合物的新形式的方法，以及用于制备含有该化合物和/或其生理上可接受的盐之一的药物的用途。

  公开号：

  US06060504A1

文献信息

• [EN] PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLOTRIAZINONE EN TANT QU'INHIBITEURS DES PI3K
  申请人：ALMIRALL SA

  公开号：WO2014060432A1

  公开（公告）日：2014-04-24

  New pyrrolotriazinone derivatives having the chemical structure of formula (I), are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks)

  新的吡咯三唑酮衍生物具有化学结构式（I），公开；以及它们的制备方法，包括它们的药物组合物和它们作为磷脂酰肌醇3-激酶（PI3Ks）抑制剂在治疗中的应用。
• Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline
  作者：Giuliana Cardillo、Luca Gentilucci、Alessandra Tolomelli、Maria Calienni、Ahmed R. Qasem、Santi Spampinato

  DOI：10.1039/b301507f

  日期：2003.4.23

  The enantiomer of endomorphin-1 (Tyr-Pro-Trp-PheNH2) and the analogues containing (S)- or (R)-β-proline have been synthesized, and their affinities towards μ-opioid receptors have been measured. As expected, the incubations of the different peptides with some commercially available enzymes showed that the presence of D-residues gave strong resistance towards digestion. The presence of β-proline alone is sufficient to confer good resistance against the hydrolysis of the biologically strategic Pro–Trp bond.

  内啡肽-1（Tyr-Pro-Trp-PheNH2）的对映体及其含（S）-或（R）-β-脯氨酸的类似物已被合成，并测定了它们对μ-阿片受体的亲和力。如预期所料，不同肽与一些商业可用酶的共育显示，D-残基的存在赋予了较强的抵抗消化能力。β-脯氨酸单独的存在就足以赋予生物学上关键的Pro-Trp键良好的抵抗水解能力。
• [EN] C17-ALKANEDIYL AND ALKENEDIYL DERIVATIVES OF OLEANOLIC ACID AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS C17-ALCANEDIYLÉS ET ALCÈNEDIYLÉS DE L'ACIDE OLÉANOLIQUE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：REATA PHARMACEUTICALS INC

  公开号：WO2014040060A1

  公开（公告）日：2014-03-13

  Disclosed herein are novel C17-alkanediyi and aikenediyl derivatives of oleanolic acid, including those of the formula (I), wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds. Methods and intermediates useful for making the compounds, and methods of using the compounds, for example, as antioxidant inflammation modulators, and compositions thereof are also provided.

  本文披露了瑞香酸的新颖C17-烷二烯基和烯二烯基衍生物，包括式(I)所示的衍生物，其中变量在此处定义。还提供了包含这些化合物的药物组合物、试剂盒和制造品。还提供了用于制备这些化合物的方法和中间体，以及使用这些化合物的方法，例如作为抗氧化炎症调节剂，以及这些化合物的组合物。
• [EN] INHIBITORS OF RAF KINASES<br/>[FR] INHIBITEURS DE KINASES RAF
  申请人：KINNATE BIOPHARMA INC

  公开号：WO2020198058A1

  公开（公告）日：2020-10-01

  Provided herein are inhibitors of receptor tyrosine kinase effector, RAF, pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.

  本文提供了受体酪氨酸激酶效应子RAF的抑制剂，包括所述化合物的药物组合物，以及使用这些化合物治疗疾病的方法。
• Discovery of BNC375, a Potent, Selective, and Orally Available Type I Positive Allosteric Modulator of α7 nAChRs
  作者：Andrew J. Harvey、Thomas D. Avery、Laurent Schaeffer、Christophe Joseph、Belinda C. Huff、Rajinder Singh、Christophe Morice、Bruno Giethlen、Anton A. Grishin、Carolyn J. Coles、Peter Kolesik、Stéphanie Wagner、Emile Andriambeloson、Bertrand Huyard、Etienne Poiraud、Dharam Paul、Susan M. O’Connor

  DOI：10.1021/acsmedchemlett.9b00001

  日期：2019.5.9

  whereas Type II PAMs both increase channel response and delay receptor desensitization. Both Type I and Type II PAMs are reported in literature, but there are limited reports describing their structure-kinetic profile relationships. Here, we report a novel class of compounds with either Type I or Type II behavior that can be tuned by the relative stereochemistry around the central cyclopropyl ring: for example

  就其对通道动力学的影响而言，α7nAChRs的正变构调节剂（PAM）可能具有不同的特性。I型PAM会放大对乙酰胆碱的峰通道响应，但似乎不会影响通道脱敏动力学，而II型PAM会增加通道响应并延迟受体脱敏。I型和II型PAM均在文献中进行了报道，但很少有报道描述它们的结构动力学轮廓关系。在这里，我们报告了一类具有I型或II型行为的新型化合物，可以通过围绕中央环丙基环的相对立体化学进行调节：例如（R，R）-13（BNC375）及其具有RR立体化学的类似物I型PAM位于中央环丙基环周围，而具有SS立体化学的同一系列化合物（例如，（S，S）-13）是使用膜片钳电生理学测量的II型PAM。通过改变苯胺环上的取代基可实现对动力学的进一步精细控制：通常，苯胺被强吸电子基团取代会降低这些化合物的II型特性。我们通过结构活性优化工作发现了BNC375，这是一种具有良好CNS-药物样性质和临床候选潜力的小分子。