(6-甲氧基吡啶-3-基)甲醇 | 58584-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (6-甲氧基吡啶-3-基)甲醇
• 中文别名: 6-甲氧基吡啶-3-基甲醇；2-甲氧基-5-羟基甲基吡啶
• 英文名称: (6-methoxypyridin-3-yl)methanol
• 英文别名: 5-hydroxymethyl-2-methoxypyridine；2-methoxy-5-hydroxymethylpyridine；6-methoxy-3-hydroxymethyl pyridine
• CAS: 58584-63-7
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: YKTYUHMWNUVAAM-UHFFFAOYSA-N

物化性质

• 沸点：
  258℃
• 密度：
  1.155
• 闪点：
  110℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  | 室温 干燥 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (6-Methoxypyridin-3-yl)methanol
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: (6-Methoxypyridin-3-yl)methanol
CAS number: 58584-63-7

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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.
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: C7H9NO2
Molecular weight: 139.2

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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

制备方法与用途

合成方法 6-甲氧基吡啶-3-基甲酸乙酯盐酸盐的合成

将6-甲氧基吡啶-3-基甲酸和无水乙醇于冰浴中搅拌下缓慢滴入氯化亚砜，1小时内滴完。滴毕后缓慢升温至50℃反应1小时，待反应液澄清后再继续升温至回流反应4小时。减压蒸除过量的乙醇和氯化亚砜，剩余物在40℃下减压干燥，得到白色固体6-甲氧基吡啶-3-基甲酸乙酯盐酸盐。

加入适量氯仿，冰水浴冷却，控温5℃剧烈搅拌并通入氨气20~30分钟。随后进行抽滤，滤饼用氯仿洗涤，滤液与洗液合并后减压浓缩，再将剩余的白色固体用乙醚重结晶，得到无色片状晶体6-甲氧基吡啶-3-基甲酸乙酯盐酸盐。

6-甲氧基吡啶-3-基甲醇的合成

在100ml三颈瓶中加入6-甲氧基吡啶-3-基甲酸乙酯盐酸盐、硼氢化钾、氯化铝和四氢呋喃，搅拌并使悬浮液回流。2小时内缓慢滴入甲醇，滴毕后继续回流反应4小时，直至TLC检测到6-甲氧基吡啶-3-基甲酸乙酯盐酸盐完全消失（展开剂：二氯甲烷/甲醇 (15:1)）。

反应液冷却至室温，加入适量水并用乙酸乙酯萃取。合并乙酸乙酯层，无水硫酸镁干燥后过滤，滤液减压浓缩，剩余的淡黄色油状物再用乙醚重结晶，最终得到白色针状晶体6-甲氧基吡啶-3-基甲醇。

反应信息

• 作为反应物：
  描述：

  (6-甲氧基吡啶-3-基)甲醇 在 manganese(IV) oxide 、 异丙基氯化镁 、 三氧化硫吡啶 、 2,4,6-三甲基苯磺酰羟胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 邻二氯苯 为溶剂， 反应 28.5h， 生成 [7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl](pyridin-4-yl)methanone
  参考文献：
  名称：

  Phosphodiesterase inhibitors. Part 6: Design, synthesis, and structure–activity relationships of PDE4-inhibitory pyrazolo[1,5-a]pyridines with anti-inflammatory activity

  摘要：

  We previously identified KCA-1490 [(-)-6-(7-methoxy-2-trifluoromethyl-pyrazolo[1,5-alpha] pyridin-4-yl)-5- methyl-4,5-dihydro-3-(2H)-pyridazinone], a dual PDE3/4 inhibitor. In the present study, we found highly potent selective PDE4 inhibitors derived from the structure of KCA-1490. Among them, N-(3,5-dichloropyridin-4-yl)-7-methoxy-2-(trifluoromethyl) pyrazolo[1,5-alpha] pyridine-4-carboxamide (2 alpha) had good anti-inflammatory effects in an animal model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.069
• 作为产物：
  描述：

  6-甲氧基-3-吡啶甲醛 在 nickel(II) chloride hexahydrate 、 三乙醇胺 、 tetrabutylammonium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72 %的产率得到(6-甲氧基吡啶-3-基)甲醇
  参考文献：
  名称：

  电化学镍催化加氢

  摘要：

  描述了一种经济有效的电化学镍催化烯烃加氢反应。该反应具有出色的底物通用性和官能团兼容性以及独特的化学选择性。值得注意的是，烷基溴和芳基溴的加氢脱溴可以使用相同的反应体系和不同的配体来实现，并且通过配体的选择可以实现烯烃加氢和加氢脱溴之间的高化学选择性。

  DOI：

  10.1002/anie.202403475

文献信息

• [EN] HETEROARYL SUBSTITUTED HETEROCYCLYL SULFONES<br/>[FR] SULFONES À HÉTÉROCYCLYLES À SUBSTITUTION HÉTÉROARYLE
  申请人：GRUENENTHAL GMBH

  公开号：WO2015158427A1

  公开（公告）日：2015-10-22

  The invention relates to aryl substituted heterocyclyl sulfones as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及芳基取代的杂环磺酮作为电压门控钙通道阻滞剂，以及含有这些化合物的药物组合物，还涉及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。
• [EN] 2 -ARYLAMINOQUINAZOLINES FOR TREATING PROLIFERATIVE DISEASES<br/>[FR] 2 -ARYLAMINOQUINAZOLINES DESTINÉES AU TRAITEMENT DES MALADIES PROLIFÉRATIVES
  申请人：NOVARTIS AG

  公开号：WO2009153313A1

  公开（公告）日：2009-12-23

  The invention provides novel compounds that are inhibitors of PDKI. Also provided are pharmaceutical compositions including the compounds, and methods of treating proliferative diseases, such as cancers, with the compounds or composition.

  这项发明提供了一种抑制PDKI的新型化合物。还提供了包括这些化合物的药物组合物，以及使用这些化合物或组合物治疗增殖性疾病，如癌症的方法。
• Benzopyridazinone and pyridopyridazinone compounds
  申请人：Syntex U.S.A. Inc.

  公开号：US05716954A1

  公开（公告）日：1998-02-10

  Benzo or pyridopyridazinones and pyridazinthiones of the formula ##STR1## wherein: X and Y are nitrogen or carbon, provided that at least one is carbon, and Z is oxygen or sulfur; R.sup.1 is hydrogen, lower alkyl, aryl, aralkyl, heterocyclo, heterocyclo lower-alkyl, heteroaryl, or heteroaralkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, lower alkyl, halo, carboxy, alkoxycarbonyl, carbamoyl, lower-alkyl carbonyl, halocarbonyl, thiomethyl, trifluoromethyl, cyano or nitro; or a pharmaceutically acceptable ester, ether or salt thereof, have been found to be useful as an anti-inflammatory, antasthmatic, immunosuppressive, anti-allograft rejection, anti-graft-vs-host rejection, autoimmune disease or analgetic agent(s).

  苯并吡啶并吡啉酮和吡啉硫酮的化学式为##STR1##其中：X和Y为氮或碳，至少一个为碳，Z为氧或硫；R.sup.1为氢、低烷基、芳基、芳基烷基、杂环烷基、杂环低烷基、杂环芳基或杂环芳基烷基；R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6独立选择自氢、低烷基、卤素、羧基、烷氧羰基、氨基甲酰基、低烷基羰基、卤代羰基、硫甲基、三氟甲基、氰基或硝基；或其药学上可接受的酯、醚或盐已被发现可用作抗炎、抗哮喘、免疫抑制、抗移植排斥、抗移植宿主排斥、自身免疫疾病或镇痛剂。
• Inhibitors of protein kinases
  申请人：Zeitlmann Lutz

  公开号：US20110224225A1

  公开（公告）日：2011-09-15

  Compounds of general Formula (I): wherein R 1 , R 2 , R 3 , R a , A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.

  通用式(I)的化合物： 其中R1、R2、R3、Ra、A、B和x的定义如本文所述，是特定于细胞周期蛋白激酶家族和/或糖原合成酶激酶3家族的抑制剂，并且在预防和/或治疗任何类型的疼痛、炎症性疾病、癌症、免疫性疾病、增殖性疾病、传染病、心血管疾病、代谢性疾病、肾脏疾病、神经和神经精神疾病以及神经退行性疾病方面具有用处。
• Development of Inhibitors against <i>Mycobacterium abscessus</i> tRNA (m¹G37) Methyltransferase (TrmD) Using Fragment-Based Approaches
  作者：Andrew J. Whitehouse、Sherine E. Thomas、Karen P. Brown、Alexander Fanourakis、Daniel S.-H. Chan、M. Daben J. Libardo、Vitor Mendes、Helena I. M. Boshoff、R. Andres Floto、Chris Abell、Tom L. Blundell、Anthony G. Coyne

  DOI：10.1021/acs.jmedchem.9b00809

  日期：2019.8.8

  with improved efficacy. tRNA (m1G37) methyltransferase (TrmD) is a promising target for novel antibiotics. It is essential in Mab and other mycobacteria, improving reading frame maintenance on the ribosome to prevent frameshift errors. In this work, a fragment-based approach was employed with the merging of two fragments bound to the active site, followed by structure-guided elaboration to design potent

  脓肿分枝杆菌 (Mab) 是一种快速增长的多重耐药非结核分枝杆菌，对囊性纤维化和其他已有慢性肺部疾病的患者构成越来越大的威胁。单克隆抗体肺部感染很难治疗，有时甚至不可能治疗，会导致肺功能加速衰退和过早死亡。因此，迫切需要开发具有改善功效的新型抗生素。tRNA (m1G37) 甲基转移酶 (TrmD) 是新型抗生素的一个有前景的靶标。它对于 Mab 和其他分枝杆菌至关重要，可改善核糖体上的读码框维护以防止移码错误。在这项工作中，采用基于片段的方法，合并与活性位点结合的两个片段，然后进行结构引导的精加工，以设计针对 Mab TrmD 的有效纳摩尔抑制剂。其中几种化合物对分枝杆菌物种表现出有希望的活性，除了 Mab 之外，还包括结核分枝杆菌和麻风分枝杆菌，支持使用 TrmD 作为开发抗分枝杆菌化合物的靶点。