N-(4-ethoxy-3-methoxy-phenethyl)-formamide | 857789-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-ethoxy-3-methoxy-phenethyl)-formamide
• 英文别名: Ameisensaeure-(3-methoxy-4-aethoxy-β-phenaethylamid)；N-(4-Aethoxy-3-methoxy-phenaethyl)-formamid；N-Formyl-O-aethyl-homovanillylamin；N-[2-(4-ethoxy-3-methoxyphenyl)ethyl]formamide
• CAS: 857789-78-7
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: SKOKCAXATWIUMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-ethoxy-3-methoxy-phenethyl)-formamide 在 甲苯 、 三氯氧磷 作用下， 生成 7-ethoxy-6-methoxy-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Kondo; Tanaka, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1929, vol. 49, p. 4

  摘要：

  DOI：
• 作为产物：
  描述：

  甲酸 、 4-乙氧基-3-甲氧基苯乙胺 反应 5.0h， 生成 N-(4-ethoxy-3-methoxy-phenethyl)-formamide
  参考文献：
  名称：

  Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s

  摘要：

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.

  DOI：

  10.1021/jm00364a013

文献信息

• Spaeth; Dobrowsky, Chemische Berichte, 1925, vol. 58, p. 1281
  作者：Spaeth、Dobrowsky

  DOI：——

  日期：——
• Kondo; Tanaka, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1929, vol. 49, p. 4
  作者：Kondo、Tanaka

  DOI：——

  日期：——
• Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s
  作者：Joan M. Caroon、Robin D. Clark、Arthur F. Kluge、Chi Ho Lee、Arthur M. Strosberg

  DOI：10.1021/jm00364a013

  日期：1983.10

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.