4-甲氧基-1-萘胺 | 16430-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-甲氧基-1-萘胺
• 英文名称: 1-amino-4-methoxynaphthalene
• 英文别名: 4-methoxy-1-naphthylamine；4-methoxynaphthalen-1-amine；4-methoxynaphthalene-1-amine；4-methoxy-1-naphthalenamine；1-Amino-4-methoxy-naphthalin；4-methoxy-β-naphthylamine
• CAS: 16430-99-2
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: JVMUPDOMGALPOW-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• 沸点：
  165 °C(Press: 7 Torr)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxynaphthalen-1-amine
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: 4-Methoxynaphthalen-1-amine
CAS number: 16430-99-2

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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：

  4-甲氧基-1-萘胺 在 三氟化硼乙醚 、 亚硝酸特丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以85%的产率得到4-methoxynaphtalene-1-diazonium tetrafluoroborate
  参考文献：
  名称：

  Deprotection of Arenediazonium Tetrafluoroborate Ethers with BBr₃

  摘要：

  Ether cleavage was carried out oil arene bearing a diazonium salt. The deprotection takes place with boron tribromide under very mild conditions in good yields without affecting the diazonium group.

  DOI：

  10.1021/jo8027906
• 作为产物：
  描述：

  1-甲氧基萘 在 palladium 10% on activated carbon 、 氢气 、 硝酸 、 乙酸酐 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-甲氧基-1-萘胺
  参考文献：
  名称：

  SB03178 的开发、临床前评估和初步剂量测定分析，SB03178 是一种用于癌症成像和治疗的首创基于苯并[h]喹啉的成纤维细胞激活蛋白-α 靶向放射治疗剂

  摘要：

  成纤维细胞激活蛋白-α (FAP) 是癌症相关成纤维细胞 (CAF) 的标志物，CAF 构成大多数癌症的重要组成部分。由于它在肿瘤生长和转移中发挥着关键作用，因此利用靶向放射性药物及时检测并识别早期发育阶段的肿瘤病变已获得重大推动力。在目前的工作中，合成了两种新型 FAP 靶向前体 SB03178 和 SB04033，由非典型苯并[]喹啉结构组成，并与诊断性放射性核素镓 68 或治疗性放射性核素镥 177 螯合，放射化学纯度≥90%，22- 76% 衰变校正放射化学产率。 Ga 标记的复合物表现出剂量依赖性 FAP 抑制作用，Ga-SB03178 的结合效力比 Ga-SB04033 高约 17 倍。为了评估其药代动力学特征，在 FAP 过表达 HEK293T:hFAP 荷瘤小鼠中进行 PET 成像和生物分布分析。虽然两种示踪剂都显示出清晰的肿瘤可视化，主要由 FAP 仲裁，在大多数外周组织中的摄取可以忽略不计，但

  DOI：

  10.1016/j.ejmech.2024.116238

文献信息

• MONNA, a Potent and Selective Blocker for Transmembrane Protein with Unknown Function 16/Anoctamin-1
  作者：Soo-Jin Oh、Seok Jin Hwang、Jonghoon Jung、Kuai Yu、Jeongyeon Kim、Jung Yoon Choi、H. Criss Hartzell、Eun Joo Roh、C. Justin Lee

  DOI：10.1124/mol.113.087502

  日期：2013.11

  Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established ([Oh et al., 2008][1]). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a −NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC50 < 10 μ M. The most potent blocker, N -((4-methoxy)-2-naphthyl)-5-nitroanthranilic acid (MONNA), had an IC50 of 0.08 μ M for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10∼30 μ M MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia. [1]: #ref-12

  跨膜蛋白16/anoctamin-1（ANO1）是一种在哺乳动物组织中广泛表达的蛋白质，具有经典钙激活氯通道（CaCC）的特性。这种蛋白质已被认为涉及许多主要的生理功能。然而，缺乏有效且选择性的阻断剂阻碍了对该通道生理功能的详细研究。在本研究中，我们利用先前建立的药物筛选方法（Oh等，2008），开发了一种对非洲爪蟾卵母细胞中内源性ANO1（xANO1）具有强效和选择性的阻断剂。我们合成了许多邻氨基苯甲酸衍生物，并确定了这些衍生物中的生物活性与取代基性质和位置之间的关联。从结构-活性关系中发现了一系列新的xANO1阻断剂化学类别。这些衍生物在萘基取代的邻氨基苯甲酸的5位含有一个−NO2基团，能完全阻断xANO1氯电流，IC50 < 10 μM。最强效的阻断剂，N -((4-甲氧基)-2-萘基)-5-硝基邻氨基苯甲酸（MONNA），对xANO1的IC50为0.08 μM。选择性测试表明，其他氯通道如bestrophin-1、氯通道蛋白2和囊性纤维化跨膜传导调节因子在10～30 μM MONNA下未被明显阻断。本研究识别出的对ANO1具有强效和选择性的阻断剂应能允许对ANO1/CaCC功能进行药理学解析，并作为治疗高血压、囊性纤维化、支气管炎、哮喘和痛觉过敏等相关疾病的潜在药物候选。
• Copper-Catalyzed N-tert-Butylation of Aromatic Amines under Mild Condi­tions Using tert-Butyl 2,2,2-Trichloroacetimidate
  作者：John Cran、Dinesh Vidhani、Marie Krafft

  DOI：10.1055/s-0033-1339107

  日期：——

  A variety of aromatic amines have been found to expediently undergo copper-catalyzed N-tert-butylation in the presence of tert-butyl 2,2,2-trichloroactimidate at room temperature.

  已经发现，在室温下，在 2,2,2-三氯亚胺酸叔丁酯存在下，多种芳香胺可以方便地进行铜催化的 N-叔丁基化反应。
• Free‐Amine‐Directed Iridium‐Catalyzed C−H Bond Activation and Cyclization of Naphthalen‐1‐amines with Diazo Compounds Leading to Naphtho[1,8‐ <i>bc</i> ]pyridines
  作者：Kelu Yan、Yongxue Lin、Yong Kong、Bin Li、Baiquan Wang

  DOI：10.1002/adsc.201801598

  日期：2019.4

  Iridium‐catalyzed C−H activation and cyclization of naphthalen‐1‐amines with diazo compounds leading to naphtho[1,8‐bc]pyridines have been developed. Different from the previous free‐amine‐directed C−H functionalization with diazo compounds that relied on the coordination of lone pair electrons or in situ formation of imine, this transformation passes through a five‐membered iridacycle intermediate containing an

  已经开发了铱催化的CH-1活化和萘-1-胺与重氮化合物的环合反应，从而生成萘[1,8- bc ]吡啶。与以前的重氮化合物基于孤对电子的配位或亚胺的原位形成的重氮化合物的游离胺定向的CH官能化不同，该转化过程通过包含N-Irσ-键的五元iridacycle中间体进行。 。它为在温和条件下合成有用的各种萘并[1,8- bc ]吡啶衍生物提供了另一种方法。
• Discovery of a Flexible Triazolylbutanoic Acid as a Highly Potent Uric Acid Transporter 1 (URAT1) Inhibitor
  作者：He Tian、Wei Liu、Zhixing Zhou、Qian Shang、Yuqiang Liu、Yafei Xie、Changying Liu、Weiren Xu、Lida Tang、Jianwu Wang、Guilong Zhao

  DOI：10.3390/molecules21111543

  日期：——

  In order to systematically explore and understand the structure–activity relationship (SAR) of a lesinurad-based hit (1c) derived from the replacement of the S atom in lesinurad with CH2, 18 compounds (1a–1r) were designed, synthesized and subjected to in vitro URAT1 inhibitory assay. The SAR exploration led to the discovery of a highly potent flexible URAT1 inhibitor, 1q, which was 31-fold more potent than parent lesinurad (IC50 = 0.23 μM against human URAT1 for 1q vs 7.18 μM for lesinurad). The present study discovered a flexible molecular scaffold, as represented by 1q, which might serve as a promising prototype scaffold for further development of potent URAT1 inhibitors, and also demonstrated that the S atom in lesinurad was not indispensable for its URAT1 inhibitory activity.

  为了系统地探索和理解基于lesinurad的命中化合物（1c）的结构-活性关系（SAR），该化合物是通过将lesinurad中的S原子替换为CH2得到的，设计并合成了18个化合物（1a–1r），并对其进行了体外URAT1抑制活性测试。SAR探索发现了一个高效的柔性URAT1抑制剂1q，其活性比母体lesinurad高31倍（对于人URAT1的IC50值，1q为0.23 μM，而lesinurad为7.18 μM）。本研究发现了一种柔性分子骨架，如1q所示，这可能作为进一步开发高效URAT1抑制剂的有前景的原型骨架，并且表明lesinurad中的S原子对其URAT1抑制活性并非必需。
• Cobalt-Catalyzed Direct Carbonylative Synthesis of Free (<i>NH</i>)-Benzo[<i>cd</i>]indol-2(1<i>H</i>)-ones from Naphthylamides
  作者：Jun Ying、Lu-Yang Fu、Guoqiang Zhong、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.9b02037

  日期：2019.7.19

  cobalt-catalyzed C–H carbonylation of naphthylamides for the synthesis of benzo[cd]indol-2(1H)-one scaffolds has been developed. The reaction employs a traceless directing group and uses benzene-1,3,5-triyl triormate as the CO source, affording various free (NH)-benzo[cd]indol-2(1H)-ones in moderate to high yields (up to 88%). Using this protocol, the total synthesis of BET bromodomain inhibitors A and B was accomplished

  已开发了钴催化的萘甲酰胺的CH羰基化反应，用于合成苯并[ cd ]吲哚-2（1 H）-一个支架。该反应采用无痕导向基团，并使用苯甲酸1,3,5-三甲酸三乙酯作为CO源，以中等至高收率提供各种游离的（NH）-苯并[ cd ]吲哚-2（1 H）-（高达88％）。使用该方案，也完成了BET溴结构域抑制剂A和B的总合成。