7-甲氧基异喹啉 | 39989-39-4

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 7-甲氧基异喹啉
• 英文名称: 7-methoxyisoquinoline
• 英文别名: 7-Methoxy-isochinolin；7-Isoquinolinyl methyl ether
• CAS: 39989-39-4
• 化学式: C₁₀H₉NO
• mdl: MFCD09030747
• 分子量: 159.188
• InChiKey: PNNUXNXZDJVGSB-UHFFFAOYSA-N

物化性质

• 熔点：
  49°C
• 沸点：
  284.68°C (rough estimate)
• 密度：
  1.1202 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R22
• 海关编码：
  2933499090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-Methoxyisoquinoline
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: 7-Methoxyisoquinoline
CAS number: 39989-39-4

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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: C10H9NO
Molecular weight: 159.2

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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

用途

7-甲氧基异喹啉是一种用于有机合成和其他化学过程的有用研究化学品。

制备

以氨基乙醛缩二乙醇及3-甲氧基苯甲醛为起始物料，通过成环反应制备得到目标化合物7-甲氧基异喹啉。其合成反应式如下：

实验操作

1. 取洁净的单口反应瓶，加入氨基乙醛缩二乙醇及3-甲氧基苯甲醛。
2. 倒入无水乙醇，反应液室温搅拌。
3. 使用薄层色谱检测反应进度。当反应进行2小时后结束反应。
4. 用4 mol·L−1 氢氧化钠水溶液调节溶液pH至约10。
5. 加热回流4小时，冷却后析出固体。
6. 过滤固体，使用乙醇重结晶。

最终可得到7-甲氧基异喹啉。

反应信息

• 作为反应物：
  描述：

  7-甲氧基异喹啉 在 吡啶盐酸盐 作用下， 以 乙酸乙酯 为溶剂， 生成 7-羟基异喹啉
  参考文献：
  名称：

  Bicyclic compound and platelet aggregation inhibitor containing the same

  摘要：

  该发明涉及一种新型化合物，其化学式表示为（1），基于纤维蛋白原拮抗作用具有出色的抑制血小板聚集作用。含有化合物（1）的血小板聚集抑制剂作为有效成分对预防和治疗血栓形成以及经皮透支式冠状动脉成形术或经皮透支式冠状动脉再通术后的再狭窄或再闭塞具有有效性。

  公开号：

  US05629321A1
• 作为产物：
  描述：

  3-methoxy-N-(2,2-dimethoxyethyl)benzylidenamine 在 硫酸 作用下， 生成 7-甲氧基异喹啉
  参考文献：
  名称：

  Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors

  摘要：

  A series of novel 2,7-disubstituted tetrahydroisoquinoline derivatives were designed and synthesized. Among these derivatives, compounds I and 2 (JTV-803) exhibited potent inhibitory activity against FXa and good selectivity with respect to other serine proteases (thrombin, plasmin, and trypsin). In addition, compound 2 exhibited potent anti-FXa activity after intravenous and oral administration to cynomolgus monkey, and showed a dose-dependent antithrombotic effect in a rat model of venous thrombosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.033

文献信息

• Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions
  作者：Stuart Pearson、Shaun Fillery、Kristin Goldberg、Julie Demeritt、Jonathan Eden、Jonathan Finlayson、Anil Patel

  DOI：10.1055/s-0037-1610223

  日期：2018.12

  indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described. Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of

  摘要 使氨磺酰氯活化的异喹啉在3组分反应中与吲哚反应，生成二氢异喹啉衍生物的文库。使用差异保护基团策略，可以进一步衍生产品。还描述了使用几种不同方法合成异喹啉原料。 使氨磺酰氯活化的异喹啉在3组分反应中与吲哚反应，生成二氢异喹啉衍生物的文库。使用差异保护基团策略，可以进一步衍生产品。还描述了使用几种不同方法合成异喹啉原料。
• Asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral Brønsted acids
  作者：Wei Wu、Yan Wang、Jing Guo、Liu Cai、Yuan Chen、Yanmin Huang、Yungui Peng

  DOI：10.1039/d0cc03201h

  日期：——

  An efficient asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate has been developed using chiral spiro phosphoric acids as catalysts. This reaction allowed the construction of a series of chiral 1,2-dihydroisoquinolines bearing a tertiary stereocenter at the C1 position with up to 98% yield and 99% ee.

  使用手性螺环磷酸作为催化剂，已经开发了异喹啉与α-（重氮甲基）膦酸酯和重氮乙酸酯的有效不对称酰基曼尼希反应。该反应允许构建一系列手性的1,2-二氢异喹啉，在C1位置带有叔立体中心，产率高达98％，ee高达99％。
• Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines
  作者：Xiangyuan Liu、Yang Liu、Guobi Chai、Baokun Qiao、Xiaowei Zhao、Zhiyong Jiang

  DOI：10.1021/acs.orglett.8b02791

  日期：2018.10.5

  With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced

  借助手性磷酸和二氰基吡嗪衍生的生色团（DPZ）光敏剂的双重有机催化体系，并在可见光照射下，将α-氨基酸衍生的氧化还原活性酯（RAE）的对映选择性Minisci型加到异喹啉中已经被开发出来。从RAE产生的各种前手性α-氨基烷基已成功引入异喹啉，以高收率提供了一系列有价值的α-异喹啉取代的手性仲胺，具有良好或优异的对映选择性。
• Metal‐ and Solvent‐Free, One‐Pot Synthesis of 3‐Unsubstituted Benzoindolizines
  作者：Lukas Schifferer、Olga García Mancheño

  DOI：10.1002/ejoc.202001245

  日期：2020.12.13

  A simple, one‐pot, metal‐free method for the synthesis of 3‐unsubstituted indolizines from readily available (iso)quinolines and propiolates is presented. Employing solvent‐free conditions, the competitive cyclization into 1,2‐disubstituted indolizines was suppressed, allowing remarkable chemoselectivity towards the synthetically valuable C1 mono‐substituted indolizines.

  提出了一种简单，单罐，无金属的方法，该方法可从容易获得的（异）喹啉和丙酸酯合成3-未取代的吲哚嗪。在无溶剂条件下，竞争性环化成1,2-二取代的吲哚嗪类化合物被抑制，从而对具有合成价值的C1单取代的吲哚嗪类化合物具有显着的化学选择性。
• Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons
  作者：Dongping Chen、Guangqing Xu、Qinghai Zhou、Lung Wa Chung、Wenjun Tang

  DOI：10.1021/jacs.7b04256

  日期：2017.7.26

  We herein describe a chiral diboron-templated highly diastereoselective and enantioselective reductive coupling of isoquinolines that provided expedited access to a series of chiral substituted bisisoquinolines in good yields and excellent ee’s under mild conditions. The method enjoys a broad substrate scope and good functional group compatibility. Mechanistic investigation suggests the reaction proceeds

  我们在本文中描述了异喹啉的手性二硼烷模板化的高度非对映选择性和对映选择性还原偶联，其在温和条件下以良好的产率和优异的ee提供了快速获得一系列手性取代的双异喹啉的途径。该方法具有广泛的底物范围和良好的官能团相容性。机理研究表明，该反应通过协同的[3,3]-σ重排而进行。