1-(2,6-二甲氧基苯氧基)丙烷-2-酮 | 14064-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,6-二甲氧基苯氧基)丙烷-2-酮
• 英文名称: 1-(2,6-dimethoxyphenoxy)acetone
• 英文别名: syringyl acetone；1-(2,6-Dimethoxy-phenoxy)-propanon-(2)；2,6-Dimethoxyphenoxyaceton；1-(2,6-Dimethoxyphenoxy)propan-2-one
• CAS: 14064-85-8
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: ZWDQFTCIRNWDHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-(2,6-二甲氧基苯氧基)丙烷-2-酮 在 盐酸 、 4 A molecular sieve 、 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 152.25h， 生成 N-(2-chloroethyl)-N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-N-[2-(2,6-dimethoxyphenoxy)-1-methylethyl]amine hydrochloride
  参考文献：
  名称：

  Structure–Activity relationships among novel phenoxybenzamine-Related β-Chloroethylamines

  摘要：

  A series of beta-chloroethylamines 5-18, structurally related to the irreversible alpha(1)-adrenoceptor antagonist phenoxy-benzamine [PB, N-benzyl-N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)amine hydrochloride, 1] and the competitive antagonist WB4101 [N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-N-[2-(2,6-dimethoxyphenoxy)ethyl]amine hydrochloride, 2], were synthesized and evaluated for their activity at alpha-adrenoceptors of the epididymal and the prostatic portion of young CD rat vas deferens. All compounds displayed irreversible antagonist activity. Most of them showed similar antagonism at both alpha(1)- and alpha(2)-adrenoceptors, whereas compounds 13 and 18, lacking substituents on both the phenoxy group and the oxyamino carbon chain, displayed a moderate alpha(1)-adrenoceptor selectivity (10-35 times), which was comparable to that of PB. Compounds 14 and 15, belonging to the benzyl series and bearing, respectively, a 2-ethoxyphenoxy and a 2-i-propoxyphenoxy moiety, were the most potent alpha(1)-adrenoceptor antagonists with an affinity value similar to that Of PB (pIC(50) values of 7.17 and 7.06 versus 7.27). Interestingly, several compounds were able to distinguish two alpha(1)-adrenoceptor subtypes in the epididymal tissue, as revealed by the discontinuity of their inhibition curves. A mean ratio of 24:76 for these alpha(1)-adrenoceptors was determined from compounds 8-10, 12, and 15-17. Furthermore, compounds 9, 10, 12, 16a, and 16b showed higher affinity towards the minor population of receptors, whereas compounds 8, 15, and 17 preferentially inhibited the major population of alpha(1)-adrenoceptors. In addition, selected pharmacological experiments demonstrated the complementary antagonism of the two series of compounds and their different, preferential affinity for one of the two alpha(1)-adrenoceptor subtypes. In conclusion, we found beta-chloroethylamines that demonstrate a multiplicity of alpha(1)-adrenoceptors in the epididymal portion of young CD rat vas deferens and, as a consequence, they are possible useful tools for alpha(1)-adrenoceptor characterization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00395-9
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 、 溴丙酮 在 potassium carbonate 作用下， 生成 1-(2,6-二甲氧基苯氧基)丙烷-2-酮
  参考文献：
  名称：

  Govindachari,T.R. et al., Indian Journal of Chemistry, 1966, vol. 4, p. 433 - 437

  摘要：

  DOI：

文献信息

• Structure–Activity relationships among novel phenoxybenzamine-Related β-Chloroethylamines
  作者：Dario Giardinà、Mauro Crucianelli、Piero Angeli、Michela Buccioni、Ugo Gulini、Gabriella Marucci、Gianni Sagratini、Carlo Melchiorre

  DOI：10.1016/s0968-0896(01)00395-9

  日期：2002.5

  A series of beta-chloroethylamines 5-18, structurally related to the irreversible alpha(1)-adrenoceptor antagonist phenoxy-benzamine [PB, N-benzyl-N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)amine hydrochloride, 1] and the competitive antagonist WB4101 [N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-N-[2-(2,6-dimethoxyphenoxy)ethyl]amine hydrochloride, 2], were synthesized and evaluated for their activity at alpha-adrenoceptors of the epididymal and the prostatic portion of young CD rat vas deferens. All compounds displayed irreversible antagonist activity. Most of them showed similar antagonism at both alpha(1)- and alpha(2)-adrenoceptors, whereas compounds 13 and 18, lacking substituents on both the phenoxy group and the oxyamino carbon chain, displayed a moderate alpha(1)-adrenoceptor selectivity (10-35 times), which was comparable to that of PB. Compounds 14 and 15, belonging to the benzyl series and bearing, respectively, a 2-ethoxyphenoxy and a 2-i-propoxyphenoxy moiety, were the most potent alpha(1)-adrenoceptor antagonists with an affinity value similar to that Of PB (pIC(50) values of 7.17 and 7.06 versus 7.27). Interestingly, several compounds were able to distinguish two alpha(1)-adrenoceptor subtypes in the epididymal tissue, as revealed by the discontinuity of their inhibition curves. A mean ratio of 24:76 for these alpha(1)-adrenoceptors was determined from compounds 8-10, 12, and 15-17. Furthermore, compounds 9, 10, 12, 16a, and 16b showed higher affinity towards the minor population of receptors, whereas compounds 8, 15, and 17 preferentially inhibited the major population of alpha(1)-adrenoceptors. In addition, selected pharmacological experiments demonstrated the complementary antagonism of the two series of compounds and their different, preferential affinity for one of the two alpha(1)-adrenoceptor subtypes. In conclusion, we found beta-chloroethylamines that demonstrate a multiplicity of alpha(1)-adrenoceptors in the epididymal portion of young CD rat vas deferens and, as a consequence, they are possible useful tools for alpha(1)-adrenoceptor characterization. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Govindachari,T.R. et al., Indian Journal of Chemistry, 1966, vol. 4, p. 433 - 437
  作者：Govindachari,T.R. et al.

  DOI：——

  日期：——