5-甲氧基-2,3-二氢异吲哚-1-酮 | 22246-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 5-甲氧基-2,3-二氢异吲哚-1-酮
• 中文别名: 6-甲氧基异吲哚酮；6-甲氧基-异吲哚啉-1-酮；5-甲氧基异吲哚啉-1-酮
• 英文名称: 5-methoxyisoindolin-1-one
• 英文别名: 5-methoxy-2,3-dihydro-1H-isoindol-1-one；5-methoxy-2,3-dihydroisoindol-1-one
• CAS: 22246-66-8
• 化学式: C₉H₉NO₂
• mdl: MFCD08437636
• 分子量: 163.176
• InChiKey: VVXUPZRABQQCKL-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161℃ (acetonitrile ethyl ether )
• 沸点：
  439.2±45.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Methoxy-2,3-dihydro-isoindol-1-one
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Methoxy-2,3-dihydro-isoindol-1-one
CAS number: 22246-66-8

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H9NO2
Molecular weight: 163.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2,3-二氢异吲哚-1-酮 在 4-二甲氨基吡啶 、 三溴化硼 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-benzyl-1-oxoisoindolin-5-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
  参考文献：
  名称：

  ISOINDOLINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THERAPY

  摘要：

  本发明涉及式(I)的异吲哚啉衍生物或其生理耐受盐。本发明还涉及包含这种异吲哚啉衍生物的药物组合物，以及利用这种异吲哚啉衍生物进行治疗目的的用途。

  公开号：

  US20130210880A1
• 作为产物：
  描述：

  (2-碘-5-甲氧基苯基)甲醇 在 正丁基锂 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.5h， 生成 5-甲氧基-2,3-二氢异吲哚-1-酮
  参考文献：
  名称：

  A concise and efficient synthesis of isoindolin-1-ones. New synthetic approach to the polycyclic framework of vitedoamine A

  摘要：

  A concise and efficient synthesis of 2,3-dihydro-1H-isoindol-1-ones based upon the Parham-type cyclization of iodinated benzyldicarbamates is reported. The synthetic potential of this approach was further emphasized by the assembly of the polycyclic framework of vitedoamine A. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.021

文献信息

• Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams
  作者：Peng‐Fei Chen、Bo Zhou、Peng Wu、Binju Wang、Long‐Wu Ye

  DOI：10.1002/anie.202113464

  日期：2021.12.20

  A Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement is disclosed that involves an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds and allows the practical and atom-economic synthesis of various valuable spirolactams. Moreover, the asymmetric version of this tandem cyclization is also achieved via kinetic resolution by chiral phosphoric acid

  公开了布朗斯台德酸催化的分子内加氢烷氧基化/克莱森重排，其涉及未活化的芳烃和杂芳族化合物的意外脱芳构化，并允许各种有价值的螺内酰胺的实用和原子经济合成。此外，这种串联环化的不对称形式也是通过手性磷酸催化的动力学拆分来实现的。
• Tyrosine Kinase Inhibitor And Uses Thereof
  申请人：Xuanzhu Pharma Co., Ltd.

  公开号：US20170112833A1

  公开（公告）日：2017-04-27

  Disclosed is a compound of Formula (I) or a pharmaceutically acceptable salt, ester, or solvate thereof, or their stereoisomers, which can be used as tyrosine kinase inhibitor. Also disclosed is a method for preparing the compound, a pharmaceutical composition and a kit comprising the compound, and uses of the compound. The compound can be used as tyrosine kinase inhibitor, or can be used to reduce or inhibit activity of EGFR or mutant thereof, such as EGFR mutant comprising T790M mutation, in a cell, or to treat and/or prevent a disease associated with overactivity of EGFR, such as cancer.

  公开了一种公式(I)的化合物或其药物可接受的盐、酯或溶剂，或它们的立体异构体，可用作酪氨酸激酶抑制剂。还公开了制备该化合物的方法、包含该化合物的药物组合物和套件，以及该化合物的用途。该化合物可用作酪氨酸激酶抑制剂，或可用于减少或抑制细胞中EGFR或其突变体的活性，例如包含T790M突变的EGFR突变体，或用于治疗和/或预防与EGFR过度活动相关的疾病，如癌症。
• Synthesis and Blocking Activities of Isoindolinone- and Isobenzofuranone-Containing Phenoxylalkylamines as Potent .ALPHA.1-Adrenoceptor Antagonists
  作者：Shou-Hua Zhang、Chun-Ye Wang、Zhen-Zhou Jiang、Pei-Zhou Ni、Jin-Pei Zhou、Bao-Min Xi、Wen-Hua Chen

  DOI：10.1248/cpb.59.96

  日期：——

  This paper describes the synthesis and blocking activities of twelve new isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α(1)-Adrenoceptor antagonists. These compounds were synthesized in moderate to good yields starting from 3,4-dimethylphenol, and characterized with (1)H-NMR, MS, IR and elemental analysis. Their blocking activities toward α(1)-Adrenoceptors were evaluated

  本文描述了十二种新的含异吲哚啉酮和异苯并呋喃酮的苯氧基烷基胺作为强力α（1）-肾上腺素受体拮抗剂的合成和阻断活性。这些化合物从3,4-二甲基苯酚开始以中等至良好的产率合成，并通过（1）H-NMR，MS，IR和元素分析进行​​表征。在离体大鼠无球藻肌肉上评估了它们对α（1）-肾上腺素受体的阻断活性。结果表明，这些化合物在阻断α（1）-肾上腺素受体方面非常强，并且大多数具有与已知有效的α（1）-肾上腺素受体拮抗剂1-（2,6-二甲基苯氧基）-2相当的活性。 -（3，4-二甲氧基苯基乙基氨基）丙烷盐酸盐（DDPH）。
• FUSED HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2103620A1

  公开（公告）日：2009-09-23

  The present invention provides a fused heterocyclic compound having a tyrosine kinase inhibitory action, which is represented by the formula: wherein R1 is a hydrogen atom, a halogen atom, or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom; R2 is a hydrogen atom, or an optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to each other to form an optionally substituted ring structure; R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to the carbon atom on ring A to form an optionally substituted ring structure; ring A is an optionally substituted benzene ring; and ring B is (i) an optionally substituted fused ring, or (ii) a pyridine ring having optionally substituted carbamoyl (the pyridine ring is optionally further substituted).

  本发明提供了一种具有酪氨酸激酶抑制作用的融合杂环化合物，其化学式如下： 其中 R1是氢原子、卤素原子或通过碳原子、氮原子或氧原子键合的可选择取代基； R2是氢原子，或通过碳原子或硫原子键合的可选择取代基，或 R1和R2，或R2和R3可选择键合在一起形成可选择取代的环结构； R3是氢原子或可选择取代的脂肪烃基，或 R3可选择键合到环A上的碳原子上形成可选择取代的环结构； 环A是可选择取代的苯环；环B是 (i) 可选择取代的融合环，或 (ii) 具有可选择取代的氨基甲酰基的吡啶环（吡啶环可进一步取代）。
• [EN] ISOINDOLONE COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR POTENTIATORS<br/>[FR] COMPOSES A BASE D'ISOINDOLONE ET LEUR UTILISATION COMME POTENTIALISATEURS DU RECEPTEUR METABOTROPIQUE DU GLUTAMATE
  申请人：ASTRAZENECA AB

  公开号：WO2006020879A1

  公开（公告）日：2006-02-23

  The present invention is directed to compounds of formula (I), wherein R1 is a ring and n is a number from 1 to 8. The invention also relates to use of the compounds in therapy as metabotropic glutamate receptor modulators, particularly in neurological and psychiatric disorders.

  本发明涉及式(I)的化合物，其中R1是一个环，n是1到8之间的数字。该发明还涉及将这些化合物用于治疗作为代谢型谷氨酸受体调节剂，特别是在神经系统和精神疾病中的用途。