2-(3,4-双(苄氧基)苯基)乙酸 | 1699-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(3,4-双(苄氧基)苯基)乙酸
• 英文名称: 3,4-dibenzyloxyphenylacetic acid
• 英文别名: (3.4-Dibenzyloxy-phenyl)-essigsaeure；2-(3,4-bis(benzyloxy)phenyl)acetic acid；2-[3,4-bis(phenylmethoxy)phenyl]acetic acid
• CAS: 1699-61-2
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: KVAFNOAGIQWNSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  109 °C
• 沸点：
  533.2±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)
• 溶解度：
  溶于乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(3,4-Bis(benzyloxy)phenyl)acetic acid
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-Bis(benzyloxy)phenyl)acetic acid
CAS number: 1699-61-2

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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: C22H20O4
Molecular weight: 348.4

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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-双(苄氧基)苯基)乙酸 在 sodium tetrahydroborate 、 甲烷磺酸 、 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 羟基酪醇
  参考文献：
  名称：

  Efficient Synthesis of Hydroxytyrosol from 3,4-Dihydroxybenzaldehyde

  摘要：

  Hydroxytyrosol is a naturally occurred orthodiphenolic component of olive oil. A variety of biological functions for this molecule have been reported. We report herein an efficient and practical method for the chemical synthesis of hydroxytyrosol from 2,3-dihydroxybenzaldehyde.

  DOI：

  10.1080/00397911.2010.531369
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 在 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 2-(3,4-双(苄氧基)苯基)乙酸
  参考文献：
  名称：

  具有降血脂、抗氧化和保肝作用的新型芝麻酚酚酸衍生物的合成与评价

  摘要：

  本研究的目的是合成一系列基于组合原理设计的芝麻酚基酚酸衍生物。所有这些化合物的降血脂活性通过Triton WR 1339诱导的急性高血脂小鼠模型进行初步筛选，其中化合物T6表现出比非诺贝特更显着的降低血浆TG和TC。还发现化合物T6显着降低高脂饮食诱导的高脂血症小鼠血浆和肝组织中的TG和TC。此外，T6显示出保肝作用，其特征性肝酶的显着改善被检查并且组织病理学观察显示化合物T6抑制肝脏中的脂质积累。T6处理后肝组织中与脂质代谢相关的PPAR-α受体水平上调。还观察到 T6 的其他有效作用，例如抗氧化和抗炎活性。基于这些发现，化合物 T6 可以作为一种有效的降血脂和保肝剂。

  DOI：

  10.1007/s00044-021-02770-1

文献信息

• 一种溴代呋喃酮酯类化合物及其制备方法及 其应用
  申请人：暨南大学

  公开号：CN108276367B

  公开（公告）日：2020-05-08

  本发明公开了一种溴代呋喃酮酯类化合物及其制备方法及应用。所述的溴代呋喃酮酯类化合物在制备治疗糖尿病足耐药菌感染药物的应用，所述的溴代呋喃酮酯类化合物作为活性成分和药学上可接受的辅料。所述的溴代呋喃酮酯类化合物的制备方法，包括如下步骤：(1)将式I所示的化合物I加入低温的溶剂中，搅拌，缓慢滴加溴素，然后升温回流反应，停止反应，冷却，待固体析出后抽滤，用还原性溶液和水洗涤滤饼，纯化，得到式II所示的化合物II；(2)将化合物II加入溶剂中，依次加入化合物III，脱水剂，催化剂，通入氮气，室温搅拌反应，后处理及纯化，得到如式IV所示的化合物IV。
• Biosynthesis. Part 24. Speculative incorporation experiments with 1-benzylisoquinolines and a logical approach via C₆–C₂and C₆–C₃precursors to the biosynthesis of hasubanonine and protostephanine
  作者：Alan R. Battersby、Raymond C. F. Jones、Rymantas Kazlauskas、Craig W. Thornber、Somsak Ruchirawat、James Staunton

  DOI：10.1039/p19810002016

  日期：——

  Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly. Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6–C2 biogenetic

  已经研究了许多可能的1-苄基四氢异喹啉类化合物，它们是Stephania japonica植物中生物碱hasubanonine（1）和protostephanine（2）的可能的高级前体，但没有明显掺入。施用仅具有一个芳香环的各种前体分子（例如酪氨酸）已证明这两种生物碱均来自两个不同的C 6 -C 2生物遗传单位。随后无法进一步引入1-苄基四氢异喹啉和双苯乙胺，这表明（a）改性的1-苄基异喹啉或（b）三加氧的C 6 –C 2中间体建筑模块。设计用于检查第一种可能性的前体，例如1-苄基-3,4-二氢异喹啉或1-苄基-1-羧基四氢异喹啉，未合并到（1）和（2）中，而两个3'，4'，5'-掺入三氧化的2-苯基乙胺。这些发现允许进一步描述对生物碱（1）和（2）的后续前体的需求。
• Encapsulated binding sites—synthetically simple receptors for the binding and transport of HCl
  作者：Keith J. Winstanley、Sarah J. Allen、David K. Smith

  DOI：10.1039/b906737j

  日期：——

  We report a receptor with an encapsulated amine/amidebinding site, which binds HCl with high affinity in organic media—the rate of HCl transport through an apolar phase is controlled by the degree of encapsulation of the HClbinding site.

  我们报道了一种具有封装胺/酰胺结合位点的受体，该受体在有机介质中与HCl具有高亲和性——HCl通过非极性相的传输速率由HCl结合位点的封装程度控制。
• Synthese von Catechol-O-methyl-transferase-hemmenden Verbindungen. In den Catecholaminmetabolismus eingreifende Substanzen. 1. Mitteilung
  作者：A. Carlsson、M. Lindqvist、S. Fila-Hromadko、H. Corrodi

  DOI：10.1002/hlca.19620450133

  日期：——

  The synthesis of a series of compounds with the general structure shown in formula I is described. These compounds, especially 3, 4-dihydroxyphenylacetamide (XVI), are potent and nontoxic inhibitors in vivo of catechol-O-methyl transferase. They compare favourably with pyrogallol and other known inhibitors of this enzyme.

  描述了具有式I所示的一般结构的一系列化合物的合成。这些化合物，特别是3,4- dihydroxyphenylacetamide（XVI），是有效的和无毒性的抑制剂在体内儿茶酚-O-甲基转移酶。它们与邻苯三酚和该酶的其他已知抑制剂相比具有优势。
• Designing New Analogs for Streamlining the Structure of Cytotoxic Lamellarin Natural Products
  作者：Kassrin Tangdenpaisal、Rattana Worayuthakarn、Supatra Karnkla、Poonsakdi Ploypradith、Pakamas Intachote、Suchada Sengsai、Busakorn Saimanee、Somsak Ruchirawat、Montakarn Chittchang

  DOI：10.1002/asia.201403361

  日期：2015.4

  Despite the therapeutic potential of marine‐derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug‐like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully

  尽管海洋来源的lamellarin天然产物具有治疗潜力，但其亲脂性质阻碍了它们的临床前开发，导致水溶性很差。为了开发更多类似药物的类似物，本研究从细胞毒性活性和亲脂性的角度简化了它们的结构。首先，成功设计了一条改良的总合成路线来构建59个系统设计的lamellarin类似物的文库，然后对其进行细胞毒性和log P测定。连同先前在我们实验室中合成的25种第一代薄片蛋白，对结构-活性和结构-亲脂性之间的关系进行了广泛的评估。我们的结果清楚地表明了层状蛋白骨架周围的其他结构要求，