3,4,5-三甲基苯乙酸 | 51719-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4,5-三甲基苯乙酸
• 英文名称: 3,4,5-trimethylphenylacetic acid
• 英文别名: (3,4,5-trimethyl-phenyl)-acetic acid；(3,4,5-Trimethyl-phenyl)-essigsaeure；3,4,5-Trimethylphenyl-essigsaeure；(3,4,5-Trimethylphenyl)acetic acid；2-(3,4,5-trimethylphenyl)acetic acid
• CAS: 51719-67-6
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: VSSHUPHLEXRDDT-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±11.0 °C(Predicted)
• 密度：
  1.075

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲基苯乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 dimethyl 6-N-(3,4,5-trimethylphenyl)acetylamino-4-chloro-1,3-isophthalate
  参考文献：
  名称：

  A Potent, Nonpeptidyl 1H-Quinolone Antagonist for the Gonadotropin-Releasing Hormone Receptor

  摘要：

  Extensive development of the structure-activity relationships of a screening lead determined three important pharmacophores for gonadotropin-releasing hormone (GnRH) receptor antagonist activity. Incorporation of the 3,4,5-trimethylphenyl group at the 3-position, 2-(2(S)-azetidinyl)ethoxy group at the 4-position, and N-4-pyrimidinylcarboxamide at the g-position of the quinolone core resulted in the identification of 4-(2-(azetidin-2(S)-yl)ethoxy)-7-chloro-2-oxo-3-(3,4,5-trimethylphenyl)-1,2-dihydroquinoline-6-carboxylic acid pyrimidin-4-ylamide (1) as a potent antagonist of the GnRH receptor. A 104-fold increase in in vitro binding affinity is observed for the GnRH receptor as compared to the initial screening lead. Compound 1 exhibits nanomolar binding activity and functional antagonism at the human receptor and is 7-fold less active at the rhesus receptor. Intravenous administration of compound 1 to rhesus monkeys results in a significant decrease of the serum levels of downstream hormones, luteinizing hormone (79% decrease in area under the curve) and testosterone (92% decrease in area under the curve), at a dose of 3 mg/kg. Quinolone 1 is a potent nonpeptidyl antagonist for the human GnRH receptor that is efficacious for the suppression of luteinizing hormone and testosterone in primates.

  DOI：

  10.1021/jm000275p
• 作为产物：
  描述：

  3',4',5'-三甲基苯乙酮 生成 3,4,5-三甲基苯乙酸
  参考文献：
  名称：

  将6-亚甲基三环[3.2.1.0 2,7 ] oct-3-en-8-ones与甲酸转化为核甲基化苯乙酸†

  摘要：

  在先前的文献[5]中，表明1，5-二甲基-6-亚甲基-三环[3.2.1.0 2,7 ] oct-3-en-8-one（2）和相关的三环酮被强力转化酸（CF 3 COOH，FSO 3 1H）与一氧化碳的损失，polymethylated卓鎓盐例如1，2，4-trimethyltropylium离子4从2（方案1）。

  DOI：

  10.1002/hlca.19740570129

文献信息

• Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit?
  作者：Keira Gaukroger、John A Hadfield、Nicholas J Lawrence、Steven Nolan、Alan T McGown

  DOI：10.1039/b306878a

  日期：——

  A series of combretastatins possessing both a trimethoxy unit and other substituents on ring A has been synthesised and tested for cytotoxicity and their ability to interact with the protein tubulin. All previous studies have indicated that the trimethoxy unit is essential for interaction with tubulin. The studies herein show that molecules possessing functionalities other than trimethoxy can also interact with tubulin. Importantly a trimethyl substituted agent 52a has shown reduced cytotoxicity, but increased potency in its ability to inhibit the assembly of tubulin.

  一系列在A环上同时具有三甲氧基单元和其他取代基的康布瑞他汀类化合物已被合成并测试了其细胞毒性和与微管蛋白相互作用的能力。以往所有研究都表明，三甲氧基单元对于与微管蛋白的相互作用至关重要。本研究表明，除了三甲氧基的功能外，其他功能的分子也能与微管蛋白相互作用。重要的是，一个三甲基取代的化合物52a显示出降低的细胞毒性，但在抑制微管蛋白组装的能力上增强了效力。
• Substituent Effects. XVII. Rearrangement in the Acetolysis of 2-Arylethyl Tosylates
  作者：Mizue Fujio、Mutsuo Goto、Yoji Seki、Masaaki Mishima、Yuho Tsuno、Masami Sawada、Yoshio Takai

  DOI：10.1246/bcsj.60.1097

  日期：1987.3

  The label scrambling within the ethylene chain of the final acetolysis products was determined for a series of α-D2 labeled 2-arylethyl tosylates by using proton NMR spectroscopy and the kΔ⁄ks values were derived from the scrambling ratios. For both buffered and unbuffered acetolysis runs log (kΔ⁄ks) were not correlated linearly with σ° or σ+. Application of the LArSR Eq. results in linear correlations

  通过使用质子 NMR 光谱，确定了一系列 α-D2 标记的甲苯磺酸 2-芳基乙酯在最终乙酰化产物的乙烯链内的标记扰乱，kΔ⁄ks 值来自扰乱比。对于缓冲和未缓冲的乙酰化运行，日志 (kΔ⁄ks) 与 σ° 或 σ+ 不呈线性相关。LArSR 方程的应用。导致具有出色精度的线性相关性，对于无缓冲运行，log (kΔ⁄ks)=−3.70 (σ°+0.63Δ\barσR+)+0.152 和 log (kΔ⁄ks)=−3.97 (σ°+0.60Δ\barσR+) )−0.207 用于缓冲运行。芳基辅助途径的 ρΔ 和 rΔ 值是根​​据上述表观值估算的，这是基于 ks 途径的小 ρs 值的合理假设。
• Substituted stilbenes and their reactions
  申请人：——

  公开号：US20040152629A1

  公开（公告）日：2004-08-05

  The present invention relates to stilbene and quinone compounds related to combretastatin A-4 and their use as anticancer compounds and prodrugs. The compounds include those with an alkyl group on the double bond of cis or trans-stilbenes, compounds with one or more (and preferably 2 or 3) alkyl group substituents on the stilbene A ring, compounds with an alkoxy group other than methoxy at position 3, 4, and/or 5 of the stilbene A ring, compounds (or prodrugs) in which BOC amino acid esters are formed with the phenolic hydroxyl at the 3-position of the B ring and compounds (or prodrugs) based on a benzoquinone B ring. The present invention further relates to the photochemical reactions of stilbene compounds, either the above compounds disclosed for the first time herein or compounds based on prior art stilbenes. These reactions include the photochemical release of an active form of the compound from a prodrug conjugate and the photochemical isomerisation of the compounds, especially from a trans to cis form of compounds. The reactions can be used alone or in combination to convert inactive or comparatively less active forms of the compounds to more active forms, thereby allowing the compounds to be selectively targeted, e.g. activating them at the site of a tumour.

  本发明涉及与康柏他定A-4相关的stilbene和quinone化合物及其作为抗癌化合物和前药的用途。这些化合物包括那些在顺式或反式stilbenes的双键上带有烷基的化合物，带有一个或多个（最好是2个或3个）烷基基团取代物的stilbene A环上的化合物，stilbene A环的3、4和/或5位置带有非甲氧基的烷氧基的化合物，以及在B环的3位的酚羟基形成BOC氨基酸酯的化合物（或前药）和基于苯醌B环的化合物（或前药）。本发明还涉及stilbene化合物的光化学反应，无论是本文首次披露的上述化合物还是基于先前技术的stilbenes的化合物。这些反应包括从前药共轭物中光化学释放出化合物的活性形式以及化合物的光化学异构化反应，特别是从顺式到反式形式的化合物。这些反应可以单独或组合使用，将化合物的非活性或相对不活性形式转化为更活跃的形式，从而使化合物能够被选择性地靶向，例如在肿瘤部位激活它们。
• [EN] METHOD OF PRODUCING 1-HEXENE<br/>[FR] PROCÉDÉ DE FABRICATION DU 1-HEXÈNE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2011016581A1

  公开（公告）日：2011-02-10

  A method of producing 1-hexene comprising: step 1: a periodic table group IV transition metal compound, an organoaluminum compound and ethylene are brought into contact with each other in a solvent to obtain a solution containing 1-hexene; and step 2: the solution obtained in step 1 is brought into contact with an aqueous solution containing a metal hydroxide and having a pH of 12.0 or higher.

  生产1-己烯的方法包括：步骤1：将周期表第IV族过渡金属化合物、有机铝化合物和乙烯在溶剂中接触，以获得含有1-己烯的溶液；步骤2：将步骤1中获得的溶液与含有金属氢氧化物且pH值为12.0或更高的水溶液接触。
• SUBSTITUTED STILBENES AND THEIR REACTIONS
  申请人：Hadfield John Anthony

  公开号：US20130023663A1

  公开（公告）日：2013-01-24

  The present invention relates to stilbene and quinine compounds related to combretastatin A-4 and their use as anticancer compounds and prodrugs. The compounds include those with an alkyl group on the double bond of cis- or trans-stilbenes, compounds with one or more (and preferably 2 or 3) alkyl group substituents on the stilbene A ring, compounds with an alkoxy group other than methoxy at position 3, 4, and/or 5 of the stilbene A ring, compounds (or prodrugs) in which BBOC amino acid esters are formed with the phenolic hydroxyl at the 3 -position of the B ring and compounds (or prodrugs) based on a benzoquinone B ring. The present invention further relates to the photochemical reactions of stilbene compounds, either the above compounds disclosed for the first time herein or compounds based on prior stilbenes. These reactions include the photochemical release of an active form of the compound from a prodrug conjugate and the photochemical isomerization of the compounds, especially from a trans to cis form of compounds. The reactions can be used alone or in combination to convert inactive or comparatively less active forms of the compounds to more active forms, thereby allowing the compounds to be selectively targeted, e.g., activating them at the site of a tumour.

  本发明涉及与Combretastatin A-4相关的Stilbene和Chinoline化合物及其作为抗癌化合物和前药的使用。这些化合物包括具有顺式或反式Stilbene双键上的烷基基团的化合物，具有一个或多个（最好是2或3个）烷基基团取代Stilbene A环的化合物，具有3、4和/或5位于Stilbene A环上的甲氧基以外的烷氧基的化合物，以及基于苯醌B环的化合物（或前药）和在B环的3位的酚羟基处形成BBOC氨基酸酯的化合物（或前药）。本发明还涉及Stilbene化合物的光化学反应，无论是首次在此处披露的上述化合物还是基于先前的Stilbenes的化合物。这些反应包括从前药共轭物中光化学释放化合物的活性形式和化合物的光化学异构化反应，特别是从顺式到反式的化合物。这些反应可以单独或组合使用，将化合物的非活性或相对不活性形式转化为更活性的形式，从而允许选择性地靶向这些化合物，例如在肿瘤部位激活它们。