4-溴-2-苯并呋喃-1(3H)-酮 | 102308-43-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 4-溴-2-苯并呋喃-1(3H)-酮
• 中文别名: 4-溴-2-苯并呋喃-13H-酮
• 英文名称: 4-bromoisobenzofuran-1(3H)-one
• 英文别名: 4-bromophthalide；4-Bromo-2-benzofuran-1[3H]-one；4-bromo-3H-2-benzofuran-1-one
• CAS: 102308-43-0
• 化学式: C₈H₅BrO₂
• 分子量: 213.03
• InChiKey: MACJSJRQNWAGJM-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  378.2±42.0 °C(Predicted)
• 密度：
  1.742±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-2-benzofuran-1(3H)-one
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-Bromo-2-benzofuran-1(3H)-one
CAS number: 102308-43-0

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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: C8H5BrO2
Molecular weight: 213.0

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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, hydrogen bromide.

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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-溴-2-苯并呋喃-1(3H)-酮 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 偶氮二异丁腈 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 为溶剂， 反应 76.25h， 生成 12-hydroxymethyl-12H-5,11a-diaza-dibenzo[b,h]fluoren-11-one
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of 22-Hydroxyacuminatine

  摘要：

  A total synthesis of 22-hydroxyacuminatine, a cytotoxic alkaloid isolated from Camptotheca acuminata, is reported. The key step in the synthesis involves the reaction of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline with a brominated phthalide to generate a substituted pentacyclic 12H-5,11a-diazadibenzo[b,h]fluoren-11-one intermediate. Despite its structural resemblance to camptothecin and luotonin A, a biological evaluation of 22-hydroxyacuminatine in a topoisomerase I-deficient cell line P388/CPT45 has confirmed that the observed cytotoxicity is not due to topoisomerase I inhibition, even though 22-hydroxyacuminatine has a hydroxyl group that can theoretically hydrogen bond to Asp533. This result is consistent with the hypothesis that pi-pi stacking is more important than hydrogen-bonding interactions in determining topoisomerase I inhibitor binding in the ternary cleavage complex.

  DOI：

  10.1021/jm051116e
• 作为产物：
  描述：

  3-溴-2-甲基苯甲酸 在 sodium persulfate 、 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 生成 4-溴-2-苯并呋喃-1(3H)-酮
  参考文献：
  名称：

  方酸酰胺催化含α，β-不饱和苄醇的不对称分子内Oxa-Michael反应：手性1-取代邻苯二酚的构建

  摘要：

  本文介绍了带有α，β-不饱和羰基的苄醇作为迈克尔受体的有机催化对映选择性分子内氧杂-迈克尔反应。使用基于金鸡纳酸方酰胺的有机催化剂，烯酮以及含苄醇的α，β-不饱和酯可提供其相应的1,3-二氢异苯并呋喃基-1-亚甲基酮和1,3-二氢异苯并呋喃基-1-亚甲基酯，且具有高对映选择性。另外，可以从1，3-二氢-2-苯并呋喃-1-醇的Wittig / oxa-Michael反应级联获得对映体富集的1，3-二氢异苯并呋喃基-1-亚甲基酮。

  DOI：

  10.1021/acs.joc.1c00715

文献信息

• Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors
  作者：Shanchao Wu、Na Liu、Guoqiang Dong、Lin Ma、Shengzheng Wang、Wencai Shi、Kun Fang、Shuqiang Chen、Jian Li、Wannian Zhang、Chunquan Sheng、Wei Wang

  DOI：10.1039/c6cc03071h

  日期：——

  An efficient redox-amination-aromatization-Friedel-Crafts acylation cascade process from trans-4-hydroxyproline and 2-formylbenzoic acids has been developed for the synthesis of pyrrolo[1,2-b]isoquinolin-10(5H)-ones. Compound 3h was identified as a new potent dual topoisomerase I/II inhibitor.

  从反式-4-羟基脯氨酸和2-甲酰基苯甲酸开发了一种有效的氧化还原胺化芳构化Friedel-Crafts酰化级联方法，用于合成吡咯并[1,2-b]异喹啉-10（5H）-。化合物3h被鉴定为新型强效双重拓扑异构酶I / II抑制剂。
• [EN] CHROMENOPYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE CHROMÉNOPYRIDINE UTILISÉS EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL PHOSPHATE KINASE
  申请人：PETRA PHARMA CORP

  公开号：WO2019126730A1

  公开（公告）日：2019-06-27

  The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I); where A1, A2, G, R1, R2, R3, R4, and W are described herein.

  这项发明涉及PI5P4K抑制剂，用于治疗癌症、神经退行性疾病、炎症性疾病和代谢性疾病，具有以下式（I）；其中A1、A2、G、R1、R2、R3、R4和W如本文所述。
• Structure−Activity Relationships for a Novel Series of Citalopram (1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile) Analogues at Monoamine Transporters
  作者：Peng Zhang、George Cyriac、Theresa Kopajtic、Yongfang Zhao、Jonathan A. Javitch、Jonathan L. Katz、Amy Hauck Newman

  DOI：10.1021/jm1005034

  日期：2010.8.26

  (+/-)-Citalopram (1, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile), and its eutomer, escitalopram (S-(+)-1) are selective serotonin reuptake inhibitors (SSRIs) that are used clinically to treat anxiety and depression. To further explore structure-activity relationships at the serotonin transporter (SERT), a series of (+/-)-4- and 5-substituted citalopram analogues were designed, synthesized, and evaluated for binding at the SERT, dopamine transporter (DAT) and norepinephrine transporter (NET) in native rodent tissue. Many of these analogues showed high SERT binding affinities (K-i = 1-40 nM) and selectivities over both NET and DAT. Selected enantiomeric pairs of analogues were synthesized and both retained enantioselectivity as with S- and wherein S > R at the SERT. In addition, the enantiomeric pairs of 1 and 5 were tested for binding at the homologous bacterial leucine transporter (LeuT), wherein low affinities and the absence of enantioselectivity suggested distinctive binding sites for these compounds at SERT as compared to LeuT. These novel ligands will provide molecular tools to elucidate drug-protein interactions at the SERT and to relate those to behavioral actions in vivo.

  (+/−)-Citalopram（1, 1-(3-(二甲基氨基)丙基)-1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈），及其eutomer（纯对映体），艾司西酞普兰（S-(+)-1）是选择性5-羟色胺再摄取抑制剂（SSRIs），临床上用于治疗焦虑和抑郁。为了进一步探索5-羟色胺转运体（SERT）处的构效关系，设计、合成了(+/-)-4-和5-取代的西酞普兰类似物，并在啮齿类动物的天然组织中评估了它们对SERT、多巴胺转运体（DAT）和去甲肾上腺素转运体（NET）的结合能力。许多这些类似物显示出高SERT结合亲和力（K-i = 1-40 nM），并且对NET和DAT具有选择性。合成了一些对映体类似物，其中S-和R-对映体在SERT处均保持了对映选择性，且S > R。此外，1和5的对映体对在同源的细菌亮氨酸转运体（LeuT）上的结合能力也被测试，结果显示低亲和力和缺乏对映选择性，这表明这些化合物在SERT上的结合位点与LeuT相比是独特的。这些新型配体将为阐明药物与蛋白质在SERT处的相互作用提供分子工具，并将这些作用与体内行为反应相关联。
• Palladium (II)‐Catalyzed Decarboxylative Cross‐Dehydrogenative Coupling: Direct Synthesis of <i>meta</i> ‐Substituted Biaryls from Aromatic Acids
  作者：Fan Pu、Lin‐Yan Zhang、Zhong‐Wen Liu、Xian‐Ying Shi

  DOI：10.1002/adsc.201800333

  日期：2018.7.16

  afford meta‐substituted biaryls in moderate to good yields. The reaction proceeds via carboxyl‐directed intermolecular cross‐dehydrogenative coupling and subsequent decarboxylation. The new C−C bonds in this transformation are formed in the ortho position of carboxyl and the reaction tolerates electron‐rich acids. Both symmetrical and unsymmetrical meta‐substituted biaryls can be directly synthesized

  已经实现了钯催化的简单芳族酸串联工艺，以中等到良好的产率提供了间位取代的联芳基。该反应通过羧基定向的分子间交叉脱氢偶联和随后的脱羧反应进行。在这种转变中，新的CC键在羧基的邻位形成，反应可耐受富电子酸。对称和不对称的间取代联芳基都可以通过这种方法直接合成。
• Palladium-Catalyzed Cross-Coupling of Ethyl Bromodifluoroacetate with Aryl Bromides or Triflates and Cross-Coupling of Ethyl Bromofluoroacetate with Aryl Iodides
  作者：Tingting Xia、Lei He、Yahu A. Liu、John F. Hartwig、Xuebin Liao

  DOI：10.1021/acs.orglett.7b00938

  日期：2017.5.19

  A palladium-catalyzed Negishi cross-coupling reaction of ethyl bromodifluoroacetate with aryl bromides or aryl triflates to construct C(sp2)–CF2 bonds is described. The reaction was conducted under mild reaction conditions, and no preparation of organozinc reagents is required. This is the first report encompassing the conversion of aryl triflates into products containing C–CF2 bonds. In addition,

  描述了钯催化的溴二氟乙酸乙酯与芳基溴化物或芳基三氟甲磺酸酯的Negishi交叉偶联反应，以构建C（sp2）-CF2键。反应在温和的反应条件下进行，不需要制备有机锌试剂。这是第一份有关将芳基三氟甲磺酸酯转化为含有C–CF2键的产物的报告。此外，在温和条件下，通过芳基碘化物与溴氟乙酸乙酯的交叉偶联，可以实现C（sp2）-CHF键的构建。