trans-2-(2-methoxyphenyl)cyclopropanecarboxylic acid | 110826-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-2-(2-methoxyphenyl)cyclopropanecarboxylic acid
• 英文别名: (1R,2R)-2-(2-methoxyphenyl)cyclopropane-1-carboxylic acid
• CAS: 110826-01-2
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QWTOSVJYKMLFEP-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2-(2-methoxyphenyl)cyclopropanecarboxylic acid 在 sodium azide 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  合成新的N-（芳基环丙基）乙酰胺和N-（芳基乙烯基）乙酰胺作为褪黑激素受体的构象受限配体

  摘要：

  已经制备了N-（芳基环丙基）乙酰胺和N-（芳基乙烯基）乙酰胺或甲基脲作为褪黑激素的约束类似物。这些新化合物对鸡脑褪黑激素受体以及重组人MT 1和MT 2受体的亲和力是通过使用2- [ 125 I]-碘降钙素作为放射性配体来评估的。在结合生物测定中，商业化激动剂阿戈美拉汀的严格的乙烯或环丙基类似物与阿戈美拉汀等效。然而，在黑色素聚集生物测定中，烯属类似物比环丙基之一更有效，但仍不如二取代的2,7-二甲氧基-萘烷化合物有效。

  DOI：

  10.1016/j.bmcl.2012.11.069
• 作为产物：
  描述：

  (E)-1-((1S,5S,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(2-methoxy-phenyl)-propenone 在 titanium(IV) isopropylate 、 palladium diacetate sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 trans-2-(2-methoxyphenyl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  Stereoselective palladium-catalyzed cyclopropanation of α,β-unsaturated carboxylic acids derivatized with oppolzer's sultam

  摘要：

  N-enoyl sultams, derived from alpha,beta-unsaturated carboxylic acids and bornane[10,2]sultam, undergo a stereoselective Pd-catalyzed cyclopropanation upon treatment with diazomethane. The stereoselectivity of the reaction is temperature dependent.

  DOI：

  10.1016/0040-4039(91)80102-c

文献信息

• Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide
  作者：Ruben Martin、Toni Moragas

  DOI：10.1055/s-0035-1560439

  日期：——

  Abstract A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components

  摘要 已经开发了镍催化的还原羧化技术来合成环丙烷羧酸。这种对用户友好且温和的转化过程在二氧化碳的大气压下进行，并利用有机卤化物或烯烃前体，因此代表了缺少相邻π组分的次要对位物的催化还原羧化反应的第一个实例。 已经开发了镍催化的还原羧化技术来合成环丙烷羧酸。这种对用户友好且温和的转化过程在二氧化碳的大气压下进行，并利用有机卤化物或烯烃前体，因此代表了缺少相邻π组分的次要对位物的催化还原羧化反应的第一个实例。
• Vallaerda, Jerk; Appelberg, Ulf; Csoeregh, Ingeborg, Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 461 - 470
  作者：Vallaerda, Jerk、Appelberg, Ulf、Csoeregh, Ingeborg、Hacksell, Uli

  DOI：——

  日期：——
• Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action
  作者：Sung Jin Cho、Niels H. Jensen、Toru Kurome、Sudhakar Kadari、Michael L. Manzano、Jessica E. Malberg、Barbara Caldarone、Bryan L. Roth、Alan P. Kozikowski

  DOI：10.1021/jm801354e

  日期：2009.4.9

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.
• N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists
  作者：Lars Erik Arvidsson、Anette M. Johansson、Uli Hacksell、J. Lars G. Nilsson、Kjell Svensson、Stephan Hjorth、Tor Magnusson、Arvid Carlsson、Per Lindberg

  DOI：10.1021/jm00396a014

  日期：1988.1

  N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.
• The First Cyclopropanation Reaction of Unmasked α<i>,</i>β-Unsaturated Carboxylic Acids:  Direct and Complete Stereospecific Synthesis of Cyclopropanecarboxylic Acids Promoted by Sm/CHI₃
  作者：José M. Concellón、Humberto Rodríguez-Solla、Carmen Simal

  DOI：10.1021/ol0709174

  日期：2007.7.1

  A samarium-promoted cyclopropanation of unmasked alpha,beta-unsaturated acids is described. This reaction can be carried out on (E)- or (Z)-alpha,beta-unsaturated carboxylic acids. In all cases the process is completely stereospecific and stereoselective. A mechanism has been proposed to explain the cyclopropanation reaction.