3-(2,6-二甲氧基苯基)丙烯酸甲酯 | 86761-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 3-(2,6-二甲氧基苯基)丙烯酸甲酯
• 英文名称: 3-(2,6-dimethoxyphenyl)acrylic acid methyl ester
• 英文别名: Methyl 3-(2,6-dimethoxyphenyl)prop-2-enoate
• CAS: 86761-34-4
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: PQLQSEUZCLHNEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,6-二甲氧基苯基)丙烯酸甲酯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到5-羟基香豆素
  参考文献：
  名称：

  An Efficient Large Scale Synthesis of Coumarins by a Dealkylative Boron-Mediated Ring Closure of 3-(Ortho-methoxyaryl)propenoic Esters

  摘要：

  Various substituted coumarins 3 were prepared via a dealkylative boron-mediated ring closure of ortho-methoxycinnamates 2.

  DOI：

  10.1080/00397919908086054
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 2,6-二甲氧基苯甲醛 以 甲苯 为溶剂， 以72%的产率得到3-(2,6-二甲氧基苯基)丙烯酸甲酯
  参考文献：
  名称：

  4-Phenoxybutoxy-substituted heterocycles – A structure–activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

  摘要：

  The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC(50) of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC(50)s of 150 nM to 10 mu M in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC(50) 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.033

文献信息

• Pyrimidin-4-one compounds
  申请人：——

  公开号：US20030087916A1

  公开（公告）日：2003-05-08

  Compound of formula (I): 1 wherein: R 1 , R 2 , R 3 and R 4 , which may be the same or different, each represent a hydrogen atom, a halogen atom or a group selected from alkyl, alkoxy, polyhaloalkyl, hydroxy, cyano, nitro and amino, or R 1 with R 2 , R 2 with R 3 , or R 3 with R 4 , together with the carbon atoms carrying them, form an optionally substituted benzene ring or an optionally substituted heteroaromatic ring, X represents an oxygen atom or a methylene group, A represents an alkylene chain, 2 represents an optionally substituted, unsaturated, nitrogen-containing heterocycle and R 5 represents an alkyl group, its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically acceptable acid. a medicinal products containing the same are useful as a double &agr; 2 /5-HT 2c antagonist.

  化合物的结构式（I）如下：其中：R1、R2、R3和R4，可以相同也可以不同，每个代表一个氢原子、卤原子或者从烷基、烷氧基、多卤代烷基、羟基、氰基、硝基和氨基中选择的基团，或者R1与R2、R2与R3、或者R3与R4，连同携带它们的碳原子一起，形成一个可选择取代的苯环或者一个可选择取代的杂芳环，X代表一个氧原子或者一个亚甲基基团，A代表一个烷基链，2代表一个可选择取代的、不饱和的、含氮的杂环，R5代表一个烷基基团，它的对映异构体和顺式异构体以及与药学上可接受的酸形成的加合盐，含有该化合物的药物制剂作为双α2/5-HT2c拮抗剂具有用途。
• Template-directed photoligation
  申请人：Amoco Corporation

  公开号：US05449602A1

  公开（公告）日：1995-09-12

  Methods, apparatus and compositions are presented for ligating ligands together which bind to a common target. One embodiment includes polynucleotide probes having photoreactive functional groups. The probes are capable of assuming substantially contiguous reactive positions on a target polynucleotide placing the photoreactive groups in juxtaposition. Activation of the photoreactive functional groups with radiant energy form a probe reaction product in which the probes are bound to each other.

  介绍了将结合到共同靶点的配体进行连接的方法、装置和组合物。其中一种实施方式包括具有光反应性功能基团的多核苷酸探针。这些探针能够在靶向多核苷酸上假定基本连续的反应位置，将光反应性基团放置在相邻位置。用辐射能量激活光反应性功能基团，形成探针反应产物，其中探针彼此结合。
• Template-directed ligation and amplification assay
  申请人：The Regents of the University of California

  公开号：US05686243A1

  公开（公告）日：1997-11-11

  A method for the detection of a target polynucleotide sequence wherein the target polynucleotide sequence is used as a template to direct hybridization of first and second polynucleotide probes to contiguous portions of the target. The hybridized probes are then ligated, preferably by covalent linkage of photoreactive functional groups present on each of the probes, to produce a ligated reaction product. The ligated reaction product is then multiplied with a polymerase such as Q-beta replicase to produce an enzyme reaction product which is then detected. The presence of the enzyme reaction product is indicative of the presence of the target polynucleotide sequence.

  一种检测目标多核苷酸序列的方法，其中目标多核苷酸序列被用作模板，引导第一和第二多核苷酸探针与目标的相邻部分杂交。然后将杂交的探针连接起来，最好通过连接在每个探针上的光敏功能基团的共价键连接，以产生连接的反应产物。然后将连接的反应产物与聚合酶（例如Q-β复制酶）一起扩增，以产生酶反应产物，然后检测。酶反应产物的存在表明目标多核苷酸序列的存在。
• US5449602A
  申请人：——

  公开号：US5449602A

  公开（公告）日：1995-09-12
• US5559134A
  申请人：——

  公开号：US5559134A

  公开（公告）日：1996-09-24