2-(tert-butyl)-4-methoxyphenyl acetate | 91401-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-(tert-butyl)-4-methoxyphenyl acetate
• 英文别名: (2-tert-butyl-4-methoxyphenyl) acetate
• CAS: 91401-26-2
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: IJMFKXAOABVKPT-UHFFFAOYSA-N

物化性质

• 沸点：
  305.7±42.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butyl)-4-methoxyphenyl acetate 在 bis(1,5-cyclooctadiene)nickel (0) 、 频那醇硼烷 、 1,3-双(2,6-二异丙苯基)咪唑啉酮-2-亚基 作用下， 反应 24.0h， 以58%的产率得到1-叔丁基-3-甲氧基苯
  参考文献：
  名称：

  乙酸芳基酯的选择性镍催化加氢脱乙酰氧基化

  摘要：

  在绿色溶剂碳酸二甲酯 (DMC) 中，使用频哪醇硼烷 (HBpin) 和镍-N-杂环卡宾 (NHC) 催化体系，将衍生自（可再生）酚醛的富电子乙酸芳基酯选择性还原为相应的芳烃。该方法适用于松木衍生的乙酸4-丙基愈创木酯。

  DOI：

  10.1002/anie.202201751
• 作为产物：
  描述：

  叔丁基对羟基茴香醚 、 乙酸酐 在 magnesium chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 72.0h， 以78%的产率得到2-(tert-butyl)-4-methoxyphenyl acetate
  参考文献：
  名称：

  乙酸芳基酯的选择性镍催化加氢脱乙酰氧基化

  摘要：

  在绿色溶剂碳酸二甲酯 (DMC) 中，使用频哪醇硼烷 (HBpin) 和镍-N-杂环卡宾 (NHC) 催化体系，将衍生自（可再生）酚醛的富电子乙酸芳基酯选择性还原为相应的芳烃。该方法适用于松木衍生的乙酸4-丙基愈创木酯。

  DOI：

  10.1002/anie.202201751

文献信息

• Hydroquinone compounds, preparation methods therefor, and use in anti-tumor or immunomodulation therapy
  申请人：Biomedical Analysis Center, Academy of Military Medical Sciences

  公开号：US10786481B2

  公开（公告）日：2020-09-29

  Disclosed are hydroquinone compounds, preparation methods therefor, and uses thereof in anti-tumor or immunomodulation. The structural formula of the hydroquinone compounds are shown by formula I, wherein X is C═O or CH2; Y is NH, O or absent; R is a substituted or unsubstituted alkyl group having at least one carbon atom, a substituted or unsubstituted cycloalkyl group having at least three carbon atoms, a substituted or unsubstituted alkenyl group or alkynyl group having at least two carbon atoms; and a substituted or unsubstituted aryl group or heteroaryl group containing at least four carbon atoms. The compounds provided slowly release 2-tert-butyl-4-methoxyphenol in vivo and maintain stable plasma concentration of 2-tert-butyl-4-methoxyphenol (T½=12˜24 h). The compounds provided by the present invention protect the phenolic hydroxyl group of 2-tert-butyl-4-methoxyphenol, avoid environmental oxidation and increase the environmental stability of drugs containing the compounds.

  本文披露了羟基喹啉化合物、其制备方法以及在抗肿瘤或免疫调节中的用途。羟基喹啉化合物的结构式如下，其中X为C═O或CH2；Y为NH、O或缺失；R为具有至少一个碳原子的取代或未取代的烷基基团，具有至少三个碳原子的取代或未取代的环烷基基团，具有至少两个碳原子的取代或未取代的烯基基团或炔基基团；以及含有至少四个碳原子的取代或未取代的芳基或杂环芳基。本发明提供的化合物在体内缓慢释放2-叔丁基-4-甲氧基苯酚，并维持2-叔丁基-4-甲氧基苯酚的稳定血浆浓度（T½=12˜24小时）。本发明提供的化合物保护2-叔丁基-4-甲氧基苯酚的酚羟基，避免环境氧化，增加含有该化合物的药物的环境稳定性。
• Simultaneous In-Cell Derivatization Pressurized Liquid Extraction for the Determination of Multiclass Preservatives in Leave-On Cosmetics
  作者：Lucia Sanchez-Prado、J. Pablo Lamas、Marta Lores、Carmen Garcia-Jares、Maria Llompart

  DOI：10.1021/ac101985h

  日期：2010.11.15

  An effective one-step sample preparation methodology for the determination of multiclass preservatives in cosmetics has been developed, applying, for the first time to this kind of matrix, pressurized liquid extraction (PLE) and a very simple, cheap, and fast derivatization procedure: acetylation with acetic anhydride and pyridine. A multifactorial experimental design has been used to evaluate and optimize the main experimental parameters potentially affecting the extraction process. In the final conditions the sample was mixed with Florisil as the dispersing sorbent and extracted with ethyl acetate for 15 min at 120 °C. One of the main goals of this work was to demonstrate the possibility of carrying out direct cosmetic preservative acetylation by simply adding the derivatization reagents into the PLE cell. The extract was then analyzed by GC/MS without any further cleanup or concentration step. The accuracy, precision, linearity, and detection limits (LODs) were evaluated to assess the performance of the proposed method. Quantitative recoveries were obtained, and relative standard deviation values were lower than 10% in all cases. The obtained LODs ranged from 0.000004% to 0.0001% (w/w), values far below the established restrictions in the European Cosmetics Regulation, making this multicomponent analytical method suitable for routine control. Finally, several cosmetic products such as moisturizing and antiwrinkle creams and lotions, hand creams, sunscreen and after-sun creams, baby lotions, and hair care products were analyzed. All the samples contained several of the target cosmetic ingredients, in some cases at quite high concentrations, although the actual European Cosmetics Regulation was fulfilled in all cases.

  该方法首次将加压液体萃取（PLE）和一种非常简单、廉价和快速的衍生程序（用乙酸酐和吡啶进行乙酰化）应用于此类基质。采用多因素实验设计来评估和优化可能影响萃取过程的主要实验参数。在最终条件下，样品与作为分散吸附剂的 Florisil 混合，并在 120 °C 下用乙酸乙酯萃取 15 分钟。这项工作的主要目的之一是证明只需将衍生化试剂加入 PLE 小室，即可直接进行化妆品防腐剂乙酰化。然后对提取物进行气相色谱/质谱分析，无需任何进一步的净化或浓缩步骤。对该方法的准确度、精密度、线性度和检测限（LOD）进行了评估。该方法的定量回收率和相对标准偏差值均低于 10%。所获得的检出限范围为 0.000004% 至 0.0001%（w/w），远远低于《欧洲化妆品条例》规定的限制值，因此这种多组分分析方法适用于日常控制。最后，对保湿抗皱霜和乳液、护手霜、防晒霜和晒后霜、婴儿乳液和护发产品等几种化妆品进行了分析。尽管所有样品都符合《欧洲化妆品条例》的规定，但所有样品中都含有多种目标化妆品成分，有些样品中的浓度还相当高。
• Atmosphere- and Solvent-Controlled Coupling and Acetylation of Phenols Induced by Visible Light
  作者：Jiangtao Meng、Yutong Zhou、Jianyu Gu、Jinfei Deng、Qianqiu Zheng、Xiushen Ye、Qiuli Yao

  DOI：10.1021/acs.joc.2c02470

  日期：2023.2.3

  A tunable coupling or acetylation of phenol derivatives with diacetyl was enabled through the switch of the atmosphere and solvent induced by visible light under metal-free conditions. Symmetric and asymmetric diphenols or binaphthols were obtained under oxygen in water or 1,1,1,3,3,3-hexafluoroisopropanol, whereas phenol acetates were formed under argon in the presence of diacetyl and acetic acid

  在无金属条件下，通过可见光诱导的气氛和溶剂的切换，可以实现苯酚衍生物与双乙酰的可调偶联或乙酰化。对称和不对称二酚或联萘酚是在水或 1,1,1,3,3,3-六氟异丙醇中的氧气下获得的，而苯酚乙酸酯是在双乙酰和乙酸存在下的氩气下形成的。控制化学和区域选择性的可能性丰富了光反应的合成多功能性。
• HYDROQUINONE COMPOUND, PREPARATION METHOD THEREFOR, AND APPLICATION IN TUMOUR RESISTANCE OR IMMUNOMODULATION
  申请人：Biomedical Analysis Center Academy of Military Medical Sciences

  公开号：EP3398934A1

  公开（公告）日：2018-11-07

  Disclosed area hydroquinone compound, a preparation method therefor, and use thereof in anti-tumor or immunomodulation. The structural formula of the hydroquinone compound is as shown by formula I, wherein X is C=O or CH2; Y is NH, O or absent; R is selected from any one of the following groups: a substituted or unsubstituted alkyl group having at least one carbon atom, a substituted or unsubstituted cycloalkyl group having at least three carbon atoms, a substituted or unsubstituted alkenyl group or alkynyl group having at least two carbon atoms; and a substituted or unsubstituted aryl group or heteroaryl group containing at least four carbon atoms. The compound provided by the present invention can slowly releases 2-tert-butyl-4-methoxyphenol in vivo, overcomes the disadvantage that the half-life of 2-tert-butyl-4-methoxyphenol directly adminisitered in the body is short (T1/2 = 0.5∼1h), and maintains stable plasma concentration of 2-tert-butyl-4-methoxyphenol (T1/2=12∼24h). The compound provided by the present invention protects the phenolic hydroxyl group of 2-tert-butyl-4-methoxyphenol, avoids the oxidation in the environment and increases the enviromental stability of drugs.

  本发明公开了一种对苯二酚化合物、其制备方法及其在抗肿瘤或免疫调节中的用途。对苯二酚化合物的结构式如式I所示，其中X为C=O或CH2；Y为NH、O或无；R选自下列任一基团：具有至少一个碳原子的取代或未取代的烷基、具有至少三个碳原子的取代或未取代的环烷基、具有至少两个碳原子的取代或未取代的烯基或炔基；以及含有至少四个碳原子的取代或未取代的芳基或杂芳基。本发明提供的化合物能在体内缓慢释放 2-叔丁基-4-甲氧基苯酚，克服了 2-叔丁基-4-甲氧基苯酚在体内直接给药半衰期短（T1/2=0.5∼1h）的缺点，并能保持 2-叔丁基-4-甲氧基苯酚血浆浓度的稳定（T1/2=12∼24h）。本发明提供的化合物保护了 2-叔丁基-4-甲氧基苯酚的酚羟基，避免了环境中的氧化，提高了药物的环境稳定性。
• HYDROQUINONE COMPOUNDS, PREPARATION METHODS THEREFOR, AND USE IN ANTI-TUMOR OR IMMUNOMODULATION THERAPY
  申请人：Biomedical Analysis Center, Academy Of Military Medical Sciences

  公开号：US20190022049A1

  公开（公告）日：2019-01-24

  Disclosed are hydroquinone compounds, preparation methods therefor, and uses thereof in anti-tumor or immunomodulation. The structural formula of the hydroquinone compounds are shown by formula I, wherein X is C═O or CH 2 ; Y is NH, O or absent; R is a substituted or unsubstituted alkyl group having at least one carbon atom, a substituted or unsubstituted cycloalkyl group having at least three carbon atoms, a substituted or unsubstituted alkenyl group or alkynyl group having at least two carbon atoms; and a substituted or unsubstituted aryl group or heteroaryl group containing at least four carbon atoms. The compounds provided slowly release 2-tert-butyl-4-methoxyphenol in vivo and maintain stable plasma concentration of 2-tert-butyl-4-methoxyphenol (T½=12˜24 h). The compounds provided by the present invention protect the phenolic hydroxyl group of 2-tert-butyl-4-methoxyphenol, avoid environmental oxidation and increase the environmental stability of drugs containing the compounds.