5-(methoxymethyl)cyclohexane-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(methoxymethyl)cyclohexane-1,3-dione
• 英文别名: 5-methoxymethyl-1,3-cyclohexanedione
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: GNBJMPXLLDWFEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(methoxymethyl)cyclohexane-1,3-dione 在 palladium diacetate molecular sieve 、 2-溴-1,3,5-三甲基苯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 7-Methoxymethyl-7,8-dihydro-6H-quinolin-5-one
  参考文献：
  名称：

  New synthetic approaches to CNS drugs. A straightforward, efficient synthesis of tetrahydroindol-4-ones and tetrahydroquinolin-5-ones via palladium-catalyzed oxidation of hydroxyenaminones

  摘要：

  We have developed a facile and efficient synthesis of new conformationally restricted butyrophenones in the indole and quinoline series via palladium-catalyzed oxidation of hydroxyenaminones, and subsequent cyclization followed by spontaneous arornatization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01901-9

文献信息

• Efficient synthesis of quinazolinones as intermediates of CNS agents via inverse-electron demand Diels–Alder reaction
  作者：Estibaliz R. Bilbao、Mario Alvarado、Christian F. Masaguer、Enrique Raviña

  DOI：10.1016/s0040-4039(02)00563-4

  日期：2002.5

  Enaminones undergo inverse electron demand Diels–Alder reaction with 1,3,5-triazine, allowing access to functionalised quinazolinones as intermediates in the synthesis of CNS agents. This reaction is highly dependent of the solvent: 1,3,5-triazine undergoes single or double [4+2] cycloadditions with enaminones, and quinazolinones or acridinediones can be selectively obtained.

  烯胺酮与1,3,5-三嗪发生逆电子需量Diels-Alder反应，从而允许官能化的喹唑啉酮类作为CNS试剂合成中的中间体。该反应高度依赖于溶剂：1,3,5-三嗪与烯胺酮进行一次或两次[4 + 2]环加成，可以选择性地获得喹唑啉酮或a啶二酮。
• Synthesis and binding affinity of new pyrazole and isoxazole derivatives as potential atypical antipsychotics
  作者：María Barceló、Enrique Raviña、Christian F. Masaguer、Eduardo Domínguez、Filipe Miguel Areias、José Brea、María I. Loza

  DOI：10.1016/j.bmcl.2007.06.045

  日期：2007.9

  We describe the synthesis and binding affinities on D(2), 5-HT(2A) and 5-HT(2C) receptors of 6-aminomethyl-6,7-dihydro-1H-indazol-4(5H)-ones and 6-aminomethyl-6,7-dihydro-3-methyl-benzo[d]isoxazol-4(5H)-ones, as conformationally constrained butyrophenone analogues. One of the new compounds showed good in vitro binding features, and a Meltzer's ratio characteristic of an atypical antipsychotic profile

  我们描述了6-氨基甲基-6,7-dihydro-1H-吲唑-4（5H）-ones和6的D（2），5-HT（2A）和5-HT（2C）受体的合成和结合亲和力-氨基甲基-6,7-二氢-3-甲基-苯并[d]异恶唑-4（5H）-构象受限的丁苯酮类似物。新化合物之一显示出良好的体外结合特性，以及非典型抗精神病药物的梅尔兹比特征。
• Synthesis and binding affinity of potential atypical antipsychotics with the tetrahydroquinazolinone motif
  作者：Laura Carro、Enrique Raviña、Eduardo Domínguez、José Brea、María I. Loza、Christian F. Masaguer

  DOI：10.1016/j.bmcl.2009.09.041

  日期：2009.11

  A series of 8 new tetrahydroquinazolinone derivatives was synthesized and evaluated for binding affinity to D-2 and 5-HT2A human receptors; in addition, some properties related to blood-brain barrier penetration were calculated. From the results of these assays, three compounds were selected for further binding tests on D-1, D-3, and 5-HT2C human receptors, which are thought to be involved in schizophrenia. From these data, compound 19b emerged as the most promising candidate based on its good binding affinities for D-1, D-2, and D-3 receptors, high affinity for 5-HT2A, low affinity for 5-HT2C receptors, and a Meltzer's ratio characteristic of an atypical antipsychotic profile. (C) 2009 Elsevier Ltd. All rights reserved.