2-(3,4,5-三甲氧基苯基)铬-4-酮 | 67858-30-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(3,4,5-三甲氧基苯基)铬-4-酮
• 英文名称: 2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
• 英文别名: 3',4',5'-trimethoxyflavone；3′,4′,5′-trimethoxyflavone；2-(3,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 67858-30-4
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: QCXAJQVDUHKDEL-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  175-176°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090
• WGK Germany：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(3,4,5-Trimethoxyphenyl)chromen-4-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: 2-(3,4,5-Trimethoxyphenyl)chromen-4-one
CAS number: 67858-30-4

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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.
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: C18H16O5
Molecular weight: 312.3

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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.

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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：

  2-(3,4,5-三甲氧基苯基)铬-4-酮 在 碘苯二乙酸 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 以89%的产率得到3-bromo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  SYNTHESIS OF 3-BROMO DERIVATIVES OF FLAVONES

  摘要：

  Various 3-halo flavones were prepared by reaction of the corresponding flavone derivatives with R4NBr/PhI(OAc)(2) system under mild reaction conditions.

  DOI：

  10.1081/scc-120003625
• 作为产物：
  描述：

  hydroxy-2' trimethoxy-3,4,5 dihydrochalcone 在 palladium(II) trifluoroacetate 、 5-硝基-1,10-菲咯啉 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以75%的产率得到2-(3,4,5-三甲氧基苯基)铬-4-酮
  参考文献：
  名称：

  钯 (II) 催化氧化环化从 2'-羟基二氢查尔酮合成黄酮和黄烷酮

  摘要：

  公开了通过有效的 Pd( II ) 催化合成黄酮和黄烷酮的不同且通用的合成路线。根据氧化剂和添加剂，这些 Pd( II ) 催化剂分别以高度原子经济的方式通过涉及脱氢的区分氧化环化序列，方便地从 2'-羟基二氢查耳酮中提供各种黄酮和黄烷酮作为常见的中间体。

  DOI：

  10.1039/d1ra01672e

文献信息

• A practical synthesis of flavones from methyl salicylate
  作者：Dhanapalan Nagarathnam、Mark Cushman

  DOI：10.1016/s0040-4020(01)87119-2

  日期：1991.1

  A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1,3-diones 8a-i, which on treatment with glacial acetic acid containing

  已经开发了一种简便的合成方法，用于将水杨酸甲酯（5）以高收率转化为黄酮1a-i。用叔丁基二甲基甲硅烷基氯（6）处理化合物5，得到O-甲硅烷基保护的酯7。将该酯7与由苯乙酮3a -i生成的锂阴离子进行缩合，得到1.3-二芳基丙烷-1,3-二酮8a-i，将其用含0.5％H 2 SO 4的冰醋酸在95- ℃处理3小时。 100°C以83–94％的收率提供了所需的黄酮1a-i。
• Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogs
  作者：Mark Cushman、Dhanapalan Nagarathnam、Debra L. Burg、Robert L. Geahlen

  DOI：10.1021/jm00106a047

  日期：1991.2

  Treatment of o-hydroxyacetophenones 2a-e with excess lithium bis(trimethylsilyl)amide followed by dialkyl carbonates gave alkyl 3-(2-hydroxyaryl)-3-oxopropanoates 3a-e. The latter substances were transformed through the reaction of their magnesium chelates with benzoyl chlorides into a series of 3-(alkoxycarbonyl)-2-arylflavones, which were subsequently elaborated into a variety of flavonoids. These

  用过量的双（三甲基甲硅烷基）酰胺锂，然后用碳酸二烷基酯处理邻羟基苯乙酮2a-e，得到3-（2-羟基芳基）-3-氧代丙酸烷基酯3a-e。后者的物质通过其镁螯合物与苯甲酰氯的反应转化为一系列的3-（烷氧基羰基）-2-芳基黄酮，随后将其精加工成各种类黄酮。测试了这些化合物抑制p56lck体外蛋白酪氨酸激酶活性的能力，该酶被认为在淋巴细胞活化过程中在介导CD4受体的信号转导中起关键作用。所有的活性化合物在2-芳基环的4'-位具有氨基或羟基取代基。本研究中制备的活性最高的物质是化合物17c，其功效比天然产物槲皮素（1）高约1个数量级。化合物17c相对于ATP是p56lck的竞争性抑制剂，并且相对于蛋白质丝氨酸/苏氨酸激酶，对蛋白质酪氨酸的抑制具有高度选择性。
• Water-mediated phosphorylative cyclodehydrogenation: An efficient preparation of flavones and flavanones
  作者：Manorama Vimal、Uma Pathak、Anand Kumar Halve

  DOI：10.1080/00397911.2019.1643484

  日期：——

  for the conversion of 2′-hydroxychalcones to flavanones and flavones has been developed. The reagent efficiently promoted one-pot conversion of 2′-hydroxychalcones to flavones through flavanones involving cyclization and oxidative dehydrogenation. By changing the stoichiometery of the reagents, the reaction can be tuned to generate either flavanone or flavone. The developed protocol was found to be applicable

  摘要 开发了一种利用 POCl3-水将 2'-羟基查耳酮转化为黄烷酮和黄酮的新合成策略。该试剂通过涉及环化和氧化脱氢的黄烷酮有效地促进了 2'-羟基查尔酮向黄酮的一锅法转化。通过改变试剂的化学计量，可以调整反应以生成黄烷酮或黄酮。发现开发的协议适用于各种 2'-羟基查尔酮。图形概要
• Rh-Catalyzed aldehydic C–H alkynylation and annulation
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1039/c9ob02670c

  日期：——

  aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-dibromoalkene followed by annulation. This protocol shows good functional group tolerance including aryl, alkenyl, alkyl and heteroaryl-1,1-dibromoalkenes. The steric/electronic

  描述了新颖的Rh催化醛CH键炔化和环化原位合成色酮和aurones。它涉及水杨醛与由1,1-二溴烯烃原位生成的1-溴炔烃进行的连续醛CH键炔化反应，然后进行环化。该协议显示出良好的官能团耐受性，包括芳基，烯基，烷基和杂芳基-1,1-二溴烯烃。在邻位羟基炔酮的碱介导的原位环化过程中证明了空间/电子效应，以生成金酮。
• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，