(3-氨基萘-2-基)甲醇 | 141281-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (3-氨基萘-2-基)甲醇
• 英文名称: (3-aminonaphthalen-2-yl)methanol
• 英文别名: 3-amino-2-hydroxymethylnaphthalene；3-amino-2-naphthalenemethanol
• CAS: 141281-58-5
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: JISDTJXWUKAFFL-UHFFFAOYSA-N

物化性质

• 沸点：
  397.4±17.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Amino-2-hydroxymethylnaphthalene
Synonyms: (3-Aminonaphthalen-2-yl)methanol

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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: 3-Amino-2-hydroxymethylnaphthalene
CAS number: 141281-58-5

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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: C11H11NO
Molecular weight: 173.2

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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：

  (3-氨基萘-2-基)甲醇 在 盐酸 、 sodium nitrite 、 硫酸 、 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 5.0h， 生成 (3-iodonaphthalen-2-yl)methanol
  参考文献：
  名称：

  [EN] GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
  [FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE POUR LE TRAITEMENT DE MALADIES

  摘要：

  本文描述了一种I式化合物，制备这种化合物的方法，含有这种化合物的药物组合物和药品，以及使用这种化合物来治疗或预防与葡萄糖酰胺合成酶（GCS）相关的疾病或症状的方法。

  公开号：

  WO2016145153A1
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 硫酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 (3-氨基萘-2-基)甲醇
  参考文献：
  名称：

  Synthesis and Properties of Ligands Based on Benzo[g]quinoline

  摘要：

  The preparation of 3-amino-2-naphthaldehyde is described. Ammonolysis of 3-hydroxy-8-naphthoic acid affords the corresponding amino acid which can be esterified and then reduced with LAH. Protection of the amino group, MnO2 oxidation of the primary alcohol to an aldehyde, and deprotection gave the amino aldehyde which is an excellent Friedlander synthon for benzo[g]quinolines. Dimethylene-bridged analogues of 2,2'-bipyridine and 2,2';6,2''-terpyridine were prepared as well as orthocyclophanes derived from tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione (TCU-2,7-dione). The absorption and emission spectra of these species are consistent with the parent benzo[g]quinoline where bathochromic shifts result from increased delocalization. The TCU derivative evidences exciplex formation so that its benzo[g]quinoline emission is almost completely quenched and an exciplex emission appears at 525 nm. Electrochemical analysis indicates that both reduction and UV absorption involve the same pi(*) orbital.

  DOI：

  10.1021/jo00083a024

文献信息

• Efficient Organoruthenium Catalysts for α‐Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines <i>via</i> Hydrogen Borrowing Strategy and their Mechanistic Studies
  作者：Ankur Maji、Anshu Singh、Neetu Singh、Kaushik Ghosh

  DOI：10.1002/cctc.202000254

  日期：2020.6.5

  for C−C bond formation and exhibited excellent performance in the dehydrogenative coupling of ketones and amides. In the synthesis of C–C bonds, alcohols were utilized as the alkylating agent. A broad range of substrates, including sterically hindered ketones and alcohols, were well tolerated under the optimized conditions (TON up to 47000 and TOF up to 11750 h−1). This ruthenium (II) catalysts were

  一个新的无膦有机金属钌（II）催化剂家族（Ru1 - Ru4），由二齿NN Schiff碱配体（L 1 -L 4，其中L 1 = N，N-二甲基-4-（（2-苯基-2- （吡啶-2-基甲基）肼基）甲基）苯胺，L 2 = N，N-二乙基-4-（（2-苯基-2-（甲基-2-基甲基）肼基）甲基）苯胺，L 3 = N， N-2-甲基-4-（（2-苯基-2-（吡啶-2-基）肼基亚甲基）甲基）苯胺和L 4= N，N-二乙基-4-（（2-苯基-2-（吡啶-2-基）肼基亚甲基）甲基）苯胺被制备并表征。这些半三明治配合物可作为C-C键形成的催化剂，在酮和酰胺的脱氢偶联中表现出出色的性能。在CC键的合成中，醇被用作烷基化剂。在最佳条件下（TON高达47000，TOF高达11750 h -1），各种各样的底物，包括位阻酮和醇，都具有良好的耐受性。该钌（II）催化剂对o的脱氢环化也具有活性-氨基苄醇，用于形成喹啉
• A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene
  作者：Zhibao Huo、Ilya D. Gridnev、Yoshinori Yamamoto

  DOI：10.1021/jo902603v

  日期：2010.2.19

  A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding

  开发了一种通过亲电环化合成取代喹啉的新的有效策略。在室温下，在CH 3 NO 2中存在亲电试剂（I 2，Br 2，ICl，NBS，NIS和HNTf 2）的情况下，1-叠氮基-2-（2-丙炔基）苯1的分子内环化过程顺利进行。或在100°C的THF中催化量的AuCl 3 / AgNTf 2的存在下，以高至高收率得到相应的喹啉2。对于亲电子试剂，根据试剂类型，E等于2可以是I，Br或H，而E等于2 在亲电催化剂的情况下，H为H。
• Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
  作者：Gargi Chakraborty、Rina Sikari、Siuli Das、Rakesh Mondal、Suman Sinha、Seemika Banerjee、Nanda D. Paul

  DOI：10.1021/acs.joc.8b03070

  日期：2019.3.1

  Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines

  通过仿生脱氢缩合/偶合反应进行仿生脱氢缩合/偶合反应合成喹啉，2-氨基喹啉和喹唑啉的简单，直接和原子经济的方法，催化方法是定义明确的廉价且易于制备的具有两个反铁磁耦​​合的单重双自由基Ni（II）催化剂。描述了单线双自由基二胺型配体。各种多取代的喹啉，2-氨基喹啉和喹唑啉由不同的低成本且易于获得的起始原料以中等至良好的产率合成。进行了一些对照实验，以了解反应机理，结果表明镍和配位的二胺配体在醇的脱氢过程中以协同方式参与。
• A nickel catalyzed acceptorless dehydrogenative approach to quinolines
  作者：Seuli Parua、Rina Sikari、Suman Sinha、Siuli Das、Gargi Chakraborty、Nanda D. Paul

  DOI：10.1039/c7ob02670f

  日期：——

  benign, one-step synthesis of substituted quinoline derivatives was achieved by acceptorless dehydrogenative coupling of o-aminobenzylalcohols with ketones and secondary alcohols catalyzed by a cheap, earth abundant and easy to prepare nickel catalyst [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinolines were synthesized

  通过廉价的，土类丰富且易于制备的镍催化剂[o（MeTAA）]催化邻氨基氨基醇与酮和仲醇的无受体脱氢偶联，从而实现了一种通用，有效且对环境无害的一步合成喹啉衍生物的方法。，具有四氮杂大环配体（tetramethyltetraaza [14] annulene（MeTAA））。从容易获得的邻氨基苯甲基醇和酮或仲醇开始，高产率地合成了多种取代的喹啉。进行一些受控反应以建立反应的无受体脱氢性质。
• Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives
  作者：Jiping Hao、Yi Xu、Zhongliang Xu、Zhiqiang Zhang、Weibo Yang

  DOI：10.1021/acs.orglett.8b03440

  日期：2018.12.21

  A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N–H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative

  描述了在温和条件下Pd催化的，高度区域选择性和立体选择性的三组分多米诺烯丙基烯丙基取代/ NH卡宾插入反应。该反应证明了广泛的底物范围和令人满意的官能团耐受性，提供了范围广泛的含烯丙基砜的氨基酸衍生物。此外，DBU不使用过氧化物或任何金属氧化剂即可介导烯丙基砜的高度非对映选择性的交叉脱氢偶联环合反应。此开发的协议提供了7元环杂环化合物，其中既包含含砜的氨基酸酯，又包含一个季碳中心。机理研究表明，在这种环状结构中发生了异常的甘氨酸转运蛋白。