(S)-1-(3-吡啶基)乙醇 | 5096-11-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (S)-1-(3-吡啶基)乙醇
• 中文别名: (S)-(-)-3-吡啶-1-乙醇
• 英文名称: (S)-1-(3-Pyridyl)ethanol
• 英文别名: (S)-3-(1-hydroxyethyl)pyridine；(1S)-1-pyridin-3-ylethanol
• CAS: 5096-11-7
• 化学式: C₇H₉NO
• mdl: MFCD07368884
• 分子量: 123.155
• InChiKey: QMDUEBURHKSKDG-LURJTMIESA-N

物化性质

• 沸点：
  80 °C(Press: 1.5 Torr)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-1-(3-Pyridyl)ethanol
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: (S)-1-(3-Pyridyl)ethanol
CAS number: 5096-11-7

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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.
Store in closed vessels, refrigerated.
Storage:

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H9NO
Molecular weight: 123.2

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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：

  (S)-1-(3-吡啶基)乙醇 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 铁粉 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.5h， 生成 3-[(1R)-1-(pyridin-3-yl)ethoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
  参考文献：
  名称：

  [EN] MAP4K1 INHIBITORS
  [FR] INHIBITEURS DE MAP4K1

  摘要：

  本发明涉及公式（I）（I）的Map4K1抑制剂，其中A，E，G，Q，R1，R2和R4的含义与说明中定义的相同，涉及包含根据本发明的化合物的制药组合物和组合物，以及创新化合物的预防和治疗用途，分别用于制造用于治疗或预防疾病的制药组合物，特别是用于肿瘤性疾病，或与异常MAP4K1信号相关的其他紊乱免疫反应或其他疾病，作为唯一药物或与其他活性成分联合使用。本发明还涉及用于制造用于治疗或预防良性增生，动脉粥样硬化疾病，败血症，自身免疫性疾病，血管疾病，病毒感染，神经退行性疾病，炎症性疾病，动脉粥样硬化疾病和男性生育控制的制药组合物的使用，分别使用上述化合物制造制药组合物。

  公开号：

  WO2022167627A1
• 作为产物：
  描述：

  3-乙酰基吡啶 在 (S)-α,α-双[3,5-双(三氟甲基)苯基]-2-吡咯烷甲醇 、 硼酸三甲酯 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(S)-1-(3-吡啶基)乙醇
  参考文献：
  名称：

  Efficient separation of a trifluoromethyl substituted organocatalyst: just add water

  摘要：

  开发了一种实用的、节省成本的标记方法，该方法利用了三氟甲基基团的疏水性，以调节含有至少50%水的水相–有机相介质应用和回收CBS前催化剂为例。

  DOI：

  10.1039/b908967e

文献信息

• Highly enantioselective carbonyl reduction with borane catalyzed by chiral spiroborate esters derived from chiral beta-aminoalcohols
  申请人：Ortiz-Marciales Margarita

  公开号：US20080200672A1

  公开（公告）日：2008-08-21

  Novel spiroborate esters derived from non-recemic 1,2-amino alcohols were examined as chiral catalyst in the borane reduction of acetophenone and other aromatic ketones at room temperature. The optically active alcohols were obtained in excellent chemical yields and up to 99% ee with less than 10% catalyst.

  从非手性1,2-氨基醇衍生的新型螺环硼酸酯作为手性催化剂在室温下用于苯乙酮和其他芳香酮的硼氢化还原反应。光学活性醇以极高的化学产率获得，ee值高达99%，催化剂用量不到10%。
• Chiral Imidazo[1,5-<i>a</i>]pyridine–Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones
  作者：Chinna Ayya Swamy P、Andrii Varenikov、Graham de Ruiter

  DOI：10.1021/acs.organomet.9b00526

  日期：2020.1.27

  report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The

  本文中，我们报告了基于咪唑并[1,5- a]的一类多用途的N-杂环卡宾配体的合成和应用融合到手性恶唑啉助剂上的]吡啶-3-吡啶骨架。这些配体合成的关键步骤涉及通过氰基偶氮盐与各种2-氨基醇的微波辅助缩合来安​​装恶唑啉官能团。所得手性双齿NHC-恶唑啉配体与铑（I）形成稳定的络合物，铑是有效的催化剂，用于结构多样的酮的对映选择性氢化硅烷化。分离出相应的仲醇，收率好（通常> 90％），对映选择性好（极好）（80-93％ee）。报道的氢化硅烷化发生在环境温度（40°C）下，具有出色的官能团耐受性。甚至带有杂环取代基的酮（例如，
• RhIII- and IrIII-Catalyzed Asymmetric Transfer Hydrogenation of Ketones in Water
  作者：Xiaofeng Wu、Xiaohong Li、Antonio Zanotti-Gerosa、Allan Pettman、Jianke Liu、Allan James Mills、Jianliang Xiao

  DOI：10.1002/chem.200701258

  日期：2008.2.27

  formate in neat water is shown to be viable with Rh-TsDPEN and Ir-TsDPEN catalysts, derived in situ from [Cp*MCl2]2 (M=Rh, Ir) and TsDPEN. A variety of ketones were reduced, including nonfunctionalized aryl ketones, heteroaryl ketones, ketoesters, and unsaturated ketones. In comparison with Ir-TsDPEN and the related Ru II catalyst, the Rh III catalyst is most efficient in water, affording enantioselectivities

  研究表明，纯净水中甲酸酯在酮中的不对称转移氢化（ATH）在Rh-TsDPEN和Ir-TsDPEN催化剂上是可行的，该催化剂原位衍生自[Cp * MCl2] 2（M = Rh，Ir）和TsDPEN。还原了多种酮，包括未官能化的芳基酮，杂芳基酮，酮酸酯和不饱和酮。与Ir-TsDPEN和相关的Ru II催化剂相比，Rh III催化剂在水中的效率最高，即使在100-1000的底物/催化剂（S / C）比下，对映选择性高达99％ee。惰性气氛。水相还原显示出高度依赖pH值；对于Rh-和Ir-TsDPEN，TOF大于50 mol mol（-1）h（-1）的最佳pH窗口分别为5.5-10.0和6.5-8.5。在pH窗口之外，根据pH的不同，还原速度会变慢或停滞。但是，对映选择性仅在酸性条件下会腐蚀。在较高的S / C比下，Rh-TsDPEN的ATH水溶液显示出对产物以及副产物的抑制作用。产物抑制似乎至少
• Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity
  作者：Tian Du、Biwen Wang、Chao Wang、Jianliang Xiao、Weijun Tang

  DOI：10.1016/j.cclet.2020.09.011

  日期：2021.3

  achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

  手性钴夹钳配合物，与非手性富电子的单膦配体结合，可催化多种芳基酮的有效不对称氢化，提供高收率和中等至优异对映选择性的手性醇（29例，最高93％ee）。值得注意的是，非手性单膦配体对反应的对映选择性表现出显着的影响。
• A convenient enantioselective CBS-reduction of arylketones in flow-microreactor systems
  作者：Sonia De Angelis、Maddalena De Renzo、Claudia Carlucci、Leonardo Degennaro、Renzo Luisi

  DOI：10.1039/c6ob00336b

  日期：——

  A convenient, versatile, and green CBS-asymmetric reduction of aryl and heteroaryl ketones has been developed by using the microreactor technology.

  一种便捷、多用途且环保的CBS不对称还原芳基和杂芳基酮的方法已经通过使用微反应器技术得以开发。