Propenal O-benzyl-oxime | 172881-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Propenal O-benzyl-oxime
• 英文别名: (Z)-N-phenylmethoxyprop-2-en-1-imine
• CAS: 172881-06-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: MNUUUFUXMFMGLW-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Propenal O-benzyl-oxime 在 Oxone 、 氢氧化钾 、 phosphate buffer 、 18-冠醚-6 作用下， 以 苯 为溶剂， 反应 312.0h， 生成 2-Hydroxy-3-isopropylamino-propionaldehyde O-benzyl-oxime
  参考文献：
  名称：

  Synthesis and β-Adrenergic Properties of (Z)-N-[3-(Alkylamino)-2-hydroxypropylidene](aryl-methyloxy)amines: Effects of the Configuration Around the Methyloxyiminomethyl (MOIM) Double Bond on the Biopharmacological Properties of MOIM-type β-Blocking Agents

  摘要：

  The N-isopropyl- (3a-g) and N-tert-butyl-substituted (4a-g) (Z)-N-(3-(amino)-2-hydroxypropylidene)(arylmethyloxy)amines were synthesized in order to compare their beta(1)- and beta(2)-adrenergic properties with those of their previously studied corresponding analogues with the E configuration (la-g and 2a-g). Compounds 3 and 4 were tested for their affinity for beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments, and the compounds with the highest affinity were also assayed for their activity towards the same types of beta-adrenoceptors by functional tests on isolated preparations. The Z-methyloxyiminomethyl (Z-MOIM) compounds 3 and 4 proved to possess, on the whole, affinity (K-i) and activity (pIC(50)) indices similar to those of the E isomers 1 and 2, thus indicating that for the MOIM-type beta-adrenergic antagonists 1-4, the type of configuration around the MOIM double bond does not have any appreciable effect either on the affinity or on the activity towards beta-adrenoceptors. These results are rationalized on the basis of the steric and electronic analogies existing between the MOIM groups of 1-4 in the two types of configurations (E and Z). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00172-2
• 作为产物：
  描述：

  三丁基乙烯基锡 、 在 四(三苯基膦)钯 potassium fluoride 作用下， 反应 3.0h， 以62%的产率得到Propenal O-benzyl-oxime
  参考文献：
  名称：

  N-Alkoxyimidoyl Bromides as a New and Efficient Coupling Partner in Pd-Catalyzed Stille Reaction

  摘要：

  N-烷氧基亚氨基溴化物已成功用作Pd催化的Stille偶联反应中与各种有机锡化合物的有效有机伙伴，并以良好至优异的收率获得了相应的O-烷基肟。

  DOI：

  10.1055/s-2001-17480

文献信息

• Synthesis and β-adrenergic properties of (E)-N-[3-(alkylamino)-2-hydroxypropylidene](methyloxy)amines substituted with an aromatic group on their [(methyloxy)imino]methyl moiety (MOIMM): an investigation into the biopharmacological effects of an aryl substitution in the class of MOIM β-blocking drugs
  作者：A Balsamo、MC Breschi、G Chiellini、L Favero、M Macchia、A Martinelli、C Martini、A Rossello、R Scatizzi

  DOI：10.1016/0223-5234(96)88293-6

  日期：1995.1

  N-Isopropyl-(5a-g) and N-t-butyl-substituted(6a-g) (E)-N-[3-(amino)-2-hydroxypropylidene](arylmethyloxy)amines, which present an aromatic ring (Ar) linked to the CH2 carbon of the [(methyloxy)imino]methyl moiety (MOIMM), were synthesized with the aim of comparing their beta-adrenergic properties with those of the previously studied completely aliphatic analogs 1,2 and 3,4. Compounds 5 and 6 were tested for their affinity towards beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments; the compounds with the highest affinity were also assayed for their beta(1) and beta(2)-adrenergic activity by functional tests on isolated preparations. The biopharmacological results show that, for the MOIM derivatives studied (1-6), the presence of an Ar substituent linked to the MOIM, as in 5 and 6, does not have any appreciable effect on the beta(1)-adrenergic properties in terms of affinity and activity; this type of substituent, on the contrary, appears to be capable of improving the beta(2)-adrenergic properties, as far as the receptor affinity is concerned. These results are discussed on the basis of a comparison of the conformational and electronic characteristics.
• Synthesis and β-Adrenergic Properties of (Z)-N-[3-(Alkylamino)-2-hydroxypropylidene](aryl-methyloxy)amines: Effects of the Configuration Around the Methyloxyiminomethyl (MOIM) Double Bond on the Biopharmacological Properties of MOIM-type β-Blocking Agents
  作者：Aldo Balsamo、Maria C. Breschi、Grazia Chiellini、Annalina Lapucci、Nicola Lazzeri、Marco Macchia、Adriano Martinelli、Eugenio Micali、Susanna Nencetti、Armando Rossello

  DOI：10.1016/s0968-0896(98)00172-2

  日期：1998.11

  The N-isopropyl- (3a-g) and N-tert-butyl-substituted (4a-g) (Z)-N-(3-(amino)-2-hydroxypropylidene)(arylmethyloxy)amines were synthesized in order to compare their beta(1)- and beta(2)-adrenergic properties with those of their previously studied corresponding analogues with the E configuration (la-g and 2a-g). Compounds 3 and 4 were tested for their affinity for beta(1)- and beta(2)-adrenoceptors by radioligand binding experiments, and the compounds with the highest affinity were also assayed for their activity towards the same types of beta-adrenoceptors by functional tests on isolated preparations. The Z-methyloxyiminomethyl (Z-MOIM) compounds 3 and 4 proved to possess, on the whole, affinity (K-i) and activity (pIC(50)) indices similar to those of the E isomers 1 and 2, thus indicating that for the MOIM-type beta-adrenergic antagonists 1-4, the type of configuration around the MOIM double bond does not have any appreciable effect either on the affinity or on the activity towards beta-adrenoceptors. These results are rationalized on the basis of the steric and electronic analogies existing between the MOIM groups of 1-4 in the two types of configurations (E and Z). (C) 1998 Elsevier Science Ltd. All rights reserved.
• N-Alkoxyimidoyl Bromides as a New and Efficient Coupling Partner in Pd-Catalyzed Stille Reaction
  作者：Sukbok Chang、Myunghee Lee、Sunggak Kim

  DOI：10.1055/s-2001-17480

  日期：——

  N-Alkoxyimidoyl bromides have been successfully employed as an efficient organic partner in the Pd-catalyzed Stille coupling reaction with various organotin compounds, and the corresponding O-alkyloximes were obtained in good to excellent yields.

  N-烷氧基亚氨基溴化物已成功用作Pd催化的Stille偶联反应中与各种有机锡化合物的有效有机伙伴，并以良好至优异的收率获得了相应的O-烷基肟。