2,3,4-trimethoxyphenoxyacetic acid | 79984-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-trimethoxyphenoxyacetic acid
• 英文别名: (2,3,4-trimethoxy-phenoxy)-acetic acid；(2,3,4-Trimethoxy-phenoxy)-essigsaeure；2-(2,3,4-trimethoxyphenoxy)acetic acid
• CAS: 79984-86-4
• 化学式: C₁₁H₁₄O₆
• 分子量: 242.229
• InChiKey: QLBVEGCBLMYBIF-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  366.3±37.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxyphenoxyacetic acid 在 aluminum oxide 、 PPA 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-[1-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-meth-(Z)-ylidene]-5,6,7-trimethoxy-benzofuran-3-one
  参考文献：
  名称：

  The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents

  摘要：

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.003
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 sodium hydroxide 、 水 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.5h， 生成 2,3,4-trimethoxyphenoxyacetic acid
  参考文献：
  名称：

  苯并呋喃的有效合成及其在制备Calea属天然产物中的应用

  摘要：

  Lewis酸催化的β-取代烯烃2-芳氧基-3-二甲基氨基丙酸甲酯3a - 3f的分子内环化反应导致短而新颖的苯并呋喃2a - 2f的合成。当使用烯烃4-二甲基氨基-3-芳氧基-3-丁烯-2-酮4a – 4f时，环化过程更快，并提供了相应的取代的2-乙酰基苯并呋喃1a – 1f。在后者中，天然存在的化合物calebertin（1a），caleprunin A（1b）和caleprunin B（1c）以较高的总收率制备。这些苯并呋喃还可以通过在前驱体中用DMFDMA对前体1-芳氧基丙烷-2-酮7a - 7c进行MW辐射直接处理，然后添加催化剂而得到，从而使路线缩短了一个步骤。

  DOI：

  10.1016/j.tet.2005.08.015

文献信息

• TUBULIN BINDING AGENTS
  申请人：The Provost, Fellows, Foundation Scholars, & the other Members of Board, of the College of the Holy

  公开号：US20150018566A1

  公开（公告）日：2015-01-15

  The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.

  该发明提供了类似于康柏他定A-4的化合物，经过改良以增强微管结合活性，在某些实施例中还具有促进在进行血管生成的血管系统中积聚（归巢活性）的能力。这些化合物基于康柏他定A-4的骨架结构，其具有一个微管结合药效团，包括两个融合环（A环和B环），其中B环被取代为（a）芳香环结构（C环）和（b）从B环上脱落的第二取代基/官能团。芳香环结构通常是一个六元环酚或苯胺结构，也可以是一个融合环结构，如取代或未取代的萘。B环上的第二取代基可以是已知可提供增强微管结合活性的取代基（例如酰基），也可以是促进B环官能化的取代基（例如羟基或胺基），或者可以是一种针对在进行血管生成的血管系统上优先表达而在静止血管系统上不表达的靶标的结合剂。
• Combretastatin a-4 derivatives having antineoplastic activity
  申请人：Lawrence James Nicholas

  公开号：US20050065213A1

  公开（公告）日：2005-03-24

  Compounds are disclosed that are designed to mimic the activity of combretastatin A-4 based on chalcone, aurone, or indanone structures, or involving benzoquinone or quinone rings. The anti-cancer activity of exemplified compounds is demonstrated in a range of in vitro and in vivo assays.

  公开了一些化合物，这些化合物是基于查尔酮、金合欢素或茚酮结构设计的，或涉及苯醌或醌环，旨在模仿紫杉醇A-4的活性。在一系列体外和体内试验中，展示了这些化合物的抗癌活性。
• Captodative olefins: methyl 2-aryloxy-3-dimethyl-aminopropenoates and their application in a new synthesis of benzofurans
  作者：Marı́a del Carmen Cruz、Joaquı́n Tamariz

  DOI：10.1016/j.tetlet.2004.01.073

  日期：2004.3

  The beta-substituted captodative olefins methyl 2-aryloxy-3-dimethylaminopropenoates 4a-h were synthesized, via amino-methylenation of the corresponding 2-phenoxyacetic esters 9a-h. Lewis acid promoted intramolecular cyclization of alkenes 4 led to benzofurans 7a-h, in an efficient synthetic approach to the benzofuran frame. (C) 2004 Elsevier Ltd. All rights reserved.
• COMBRETASTATIN A-4 DERIVATIVES HAVING ANTINEOPLASTIC ACTIVITY
  申请人：CANCER RESEARCH TECHNOLOGY LIMITED

  公开号：EP1444190A1

  公开（公告）日：2004-08-11
• [EN] COMBRETASTATIN A-4 DERIVATIVES HAVING ANTINEOPLASTIC ACTIVITY<br/>[FR] DERIVES DE LA COMBRETASTATINE A-4 A EFFETS ANTINEOPLASIQUES
  申请人：PATERSON INST FOR CANCER RES

  公开号：WO2003040077A1

  公开（公告）日：2003-05-15

  Compounds are disclosed that are designed to mimic the activity of combretastatin A-4 based on chalcone, aurone, or indanone structures, or involving benzoquinone or quinone rings. The anti-cancer activity of exemplified compounds is demonstrated in a range of in vitro and in vivo assays.