1-(2-ethoxyphenoxy)acetone | 344309-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-ethoxyphenoxy)acetone
• 英文别名: o-Ethoxyphenoxyaceton；1-(2-Ethoxyphenoxy)-2-propanone；1-(2-ethoxyphenoxy)propan-2-one
• CAS: 344309-42-8
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD12145573
• 分子量: 194.23
• InChiKey: ZBYSCGPMXUZBJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-ethoxyphenoxy)acetone 在 platinum(IV) oxide 、 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 丁酮 为溶剂， 反应 6.0h， 生成 5-{2-[2-(2-Ethoxy-phenoxy)-1-methyl-ethylamino]-1-hydroxy-ethyl}-2-methyl-benzenesulfonamide; hydrochloride
  参考文献：
  名称：

  Studies on benzenesulfonamide derivatives with .ALPHA.- and .BETA.-adrenergic antagonistic and antihypertensive activities.

  摘要：

  通过两种方法从乙酰苯磺酰胺类化合物（II）制备了新型α和β肾上腺素能阻断剂苯磺酰胺衍生物（Ia-z）。对这些化合物进行了α和β阻断活性测试，并讨论了它们的结构-活性关系。所有目标化合物都有两个不对称中心，因此由两种非对映异构体组成。5-[1-羟基-2-[3-(2-甲氧基苯基)-1-甲基丙氨基]乙基]-2-甲基苯磺酰胺（Ir）和 5-[1-羟基-2-[2-2-(2-甲氧基苯氧基)-1-甲基乙基氨基]乙基]-2-甲基苯磺酰胺（Iu）显示了强效的α和β-阻断活性，并分别被分离成两种非对映异构体（Ir-A 和 Ir-B 以及 Iu-A 和 Iu-B）。结果发现，一种异构体主要具有 β-阻断活性，而另一种异构体主要具有 α-阻断活性。此外，研究人员还对几种具有较强α和β阻断活性的化合物进行了研究，以观察它们在有意识的自发性高血压大鼠体内的降压活性。在测试的化合物中，Ir 和 Iu 的活性最高，它们比拉贝洛尔更强。Ir和Iu化合物作为强效降压药可能具有实用价值。

  DOI：

  10.1248/cpb.30.4092

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.
• RUJIKURA, TAKASHI;NIIGATA, KUNIHIRO;HASHIMOTO, SHINICHI;IMAI, KAZUO;TAKEN+, CHEM. AND PHARM. BULL., 1982, 30, N 11, 4092-4101
  作者：RUJIKURA, TAKASHI、NIIGATA, KUNIHIRO、HASHIMOTO, SHINICHI、IMAI, KAZUO、TAKEN+

  DOI：——

  日期：——