2-(5-甲氧基苯并呋喃-3-基)乙酸甲酯 | 118610-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-(5-甲氧基苯并呋喃-3-基)乙酸甲酯
• 英文名称: methyl 2-(5-methoxybenzofuran-3-yl)acetate
• 英文别名: 5-methoxy-3-benzofuranacetic acid methylester；3-Benzofuranacetic acid, 5-methoxy-, methyl ester；methyl 2-(5-methoxy-1-benzofuran-3-yl)acetate
• CAS: 118610-60-9
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: BFKFTCAHLXGCDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  315.7±27.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-甲氧基苯并呋喃-3-基)乙酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到2-(5-methoxybenzofuran-3-yl)ethanol
  参考文献：
  名称：

  Benzofuran bioisosteres of hallucinogenic tryptamines

  摘要：

  The benzofuran analogues of the hallucinogens 5-methoxy-NN-dimethyltryptamine and 5-methoxy-alpha-methyl-tryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled with [I-125]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane ([I-125]DOI) and [H-3]-8-hydroxy-2-(N,N-di-n-propylamino)tetralin ([H-3]-8-OH-DPAT), respectively. At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTA1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor. It is suggested that benzofurans may be useful in the design of serotonin receptor ligands.

  DOI：

  10.1021/jm00089a017
• 作为产物：
  描述：

  2,5-二甲氧基苯甲酸 在 草酰氯 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 反应 54.0h， 生成 2-(5-甲氧基苯并呋喃-3-基)乙酸甲酯
  参考文献：
  名称：

  取代萘并呋喃为致幻剂苯乙胺-麦角灵杂合分子，具有意想不到的毒蕈碱拮抗活性。

  摘要：

  合成了一系列取代的消旋萘并呋喃，作为两种主要的典型致幻药物类别（苯乙胺和色胺/麦角灵）的“混合”分子。尽管据推测这些新药可能对5-羟色胺5-HT2A / 2C受体亚型具有很高的亲和力，但仍观察到了对毒蕈碱受体的出乎意料的亲和力。最初合成用于本研究的化合物为（+/-）-抗-和合成-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘[1,8-bc]呋喃（4a ，b）和它们的8-溴衍生物4c，d。首先在训练中区分盐水与LSD酒石酸盐（0. 08 mg / kg）的大鼠中，分析了溴化伯胺4c，d在双杠杆药物歧视（DD）范式中的活性。还有4c 评估d在克隆的人5-HT 2A，5-HT 2B和5-HT 2C受体上与激动剂和拮抗剂放射性配体竞争的能力。在这些初步分析中发现顺式非对映异构体具有最高活性后，N-烷基化类似物syn-N，N-N-二甲基-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘并[1

  DOI：

  10.1021/jm980076u

文献信息

• CNS affecting 5-oxy-3-aminomethyl-dihydro-benzofurans and benzothiophenes
  申请人：H. Lundbeck A/S

  公开号：US04847254A1

  公开（公告）日：1989-07-11

  The present invention relates to 3-aminomethyl derivatives of indane, dihydrobenzofurane, dihydrobenzothiophene, and indoline, acid addition salts thereof, isomers thereof, methods of preparation, pharmaceutical compositions and method of treating CNS-disorders such as schizophrenia, Parkinson's disease, depression, anxiety, migraine and senile dementia, or in the cure of cardiovascular diseases, by administering such a derivative.

  本发明涉及吲烷、二氢苯并呋喃、二氢苯并噻吩和吲哚啉的3-氨基甲基衍生物，其酸加成盐、异构体、制备方法、药物组合物以及通过施用此类衍生物治疗中枢神经系统疾病如精神分裂症、帕金森病、抑郁症、焦虑症、偏头痛和老年痴呆症，或在治疗心血管疾病中的方法。
• Asymmetric [4 + 3] Cycloadditions between Benzofuranyldiazoacetates and Dienes:  Formal Synthesis of (+)-Frondosin B
  作者：Jeremy P. Olson、Huw M. L. Davies

  DOI：10.1021/ol702844g

  日期：2008.2.1

  The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh2(R-DOSP)4, generates formal [4+3] cycloadducts with >94% de and 91-98% ee. The reaction proceeds by a tandem cyclopropanation/Cope rearrangement followed by a stereoselective tautomerization. This methodology was extended to a formal synthesis of (+)-frondosin B.

  苯并呋喃基重氮乙酸酯与四羧酸二铑Rh2（R-DOSP）4催化的1,3-二烯发生反应，生成正式的[4 + 3]环加合物，其de> 94％，ee为91-98％。该反应通过串联环丙烷化/ Cope重排，随后进行立体选择性互变异构而进行。此方法扩展到（+）-frondosin B的形式合成。
• Benzofuran bioisosteres of hallucinogenic tryptamines
  作者：Zbigniew Tomaszewski、Michael P. Johnson、Xuemei Huang、David E. Nichols

  DOI：10.1021/jm00089a017

  日期：1992.5

  The benzofuran analogues of the hallucinogens 5-methoxy-NN-dimethyltryptamine and 5-methoxy-alpha-methyl-tryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled with [I-125]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane ([I-125]DOI) and [H-3]-8-hydroxy-2-(N,N-di-n-propylamino)tetralin ([H-3]-8-OH-DPAT), respectively. At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTA1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor. It is suggested that benzofurans may be useful in the design of serotonin receptor ligands.
• Substituted Naphthofurans as Hallucinogenic Phenethylamine−Ergoline Hybrid Molecules with Unexpected Muscarinic Antagonist Activity
  作者：Aaron P. Monte、Danuta Marona-Lewicka、Mechelle M. Lewis、Richard B. Mailman、David B. Wainscott、David L. Nelson、David E. Nichols

  DOI：10.1021/jm980076u

  日期：1998.6.1

  have the highest activity in these preliminary assays, the N-alkylated analogues syn-N,N-dimethyl-4-amino-6-methoxy-2a,3,4, 5-tetrahydro-2H-naphtho[1,8-bc]furan (4e) and syn-N, N-dipropyl-4-amino-6-methoxy-2a,3,4,5-tetrahydro-2H-naphtho[1, 8-bc]furan (4f) were prepared and assayed for their affinities at [3H]ketanserin-labeled 5-HT2A and [3H]-8-OH-DPAT-labeled 5-HT1A sites. All of the molecules tested

  合成了一系列取代的消旋萘并呋喃，作为两种主要的典型致幻药物类别（苯乙胺和色胺/麦角灵）的“混合”分子。尽管据推测这些新药可能对5-羟色胺5-HT2A / 2C受体亚型具有很高的亲和力，但仍观察到了对毒蕈碱受体的出乎意料的亲和力。最初合成用于本研究的化合物为（+/-）-抗-和合成-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘[1,8-bc]呋喃（4a ，b）和它们的8-溴衍生物4c，d。首先在训练中区分盐水与LSD酒石酸盐（0. 08 mg / kg）的大鼠中，分析了溴化伯胺4c，d在双杠杆药物歧视（DD）范式中的活性。还有4c 评估d在克隆的人5-HT 2A，5-HT 2B和5-HT 2C受体上与激动剂和拮抗剂放射性配体竞争的能力。在这些初步分析中发现顺式非对映异构体具有最高活性后，N-烷基化类似物syn-N，N-N-二甲基-4-氨基-6-甲氧基-2a，3,4,5-四氢-2H-萘并[1