(E)-2-(5-Methoxy)phenol 4-(N-Benzyloxycarbonyl)piperidinyl-methanone O-Acetyl Oxime | 84163-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(5-Methoxy)phenol 4-(N-Benzyloxycarbonyl)piperidinyl-methanone O-Acetyl Oxime
• 英文别名: benzyl 4-[(E)-N-acetyloxy-C-(2-hydroxy-4-methoxyphenyl)carbonimidoyl]piperidine-1-carboxylate
• CAS: 84163-48-4
• 化学式: C₂₃H₂₆N₂O₆
• 分子量: 426.469
• InChiKey: PMFQQZXEPFQLSD-ZNTNEXAZSA-N

物化性质

• 沸点：
  588.7±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-2-(5-Methoxy)phenol 4-(N-Benzyloxycarbonyl)piperidinyl-methanone O-Acetyl Oxime 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 phenylmethyl 4-(6-methoxy-1,2-benzisoxazolyl-3-yl)-1-piperidinecarboxylate
  参考文献：
  名称：

  Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles

  摘要：

  The synthesis of a series of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles is described. The neuroleptic activity of the series was evaluated by utilizing the climbing mice assay and inhibition of [3H]spiroperidol binding. Structure-activity relationships were studied by variation of the substituent on the benzisoxazole ring with concomitant variation of four different 1-piperidinyl substituents. Maximum neuroleptic activity was realized when there was a 6-fluoro substituent on the benzisoxazole ring. The 1-piperidinyl substituent appeared less significant, although in most cases, the (1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl group imparted maximum potency. The most potent compound in both assays was 6-fluoro-3-[1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl) propyl]-4-piperidinyl]-1,2-benzisoxazole (11b).

  DOI：

  10.1021/jm00383a012
• 作为产物：
  描述：

  乙酸酐 、 4-[[(E)-Hydroxyimino]-(2-hydroxy-4-methoxy-phenyl)-methyl]-piperidine-1-carboxylic acid benzyl ester 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (E)-2-(5-Methoxy)phenol 4-(N-Benzyloxycarbonyl)piperidinyl-methanone O-Acetyl Oxime
  参考文献：
  名称：

  Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles

  摘要：

  The synthesis of a series of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles is described. The neuroleptic activity of the series was evaluated by utilizing the climbing mice assay and inhibition of [3H]spiroperidol binding. Structure-activity relationships were studied by variation of the substituent on the benzisoxazole ring with concomitant variation of four different 1-piperidinyl substituents. Maximum neuroleptic activity was realized when there was a 6-fluoro substituent on the benzisoxazole ring. The 1-piperidinyl substituent appeared less significant, although in most cases, the (1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl group imparted maximum potency. The most potent compound in both assays was 6-fluoro-3-[1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl) propyl]-4-piperidinyl]-1,2-benzisoxazole (11b).

  DOI：

  10.1021/jm00383a012

文献信息

• STRUPCZEWSKI, J. T.;ALLEN, R. C.;GARDNER, B. A.;SCHMID, B. L.;STACHE, U.;+, J. MED. CHEM., 1985, 28, N 6, 761-769
  作者：STRUPCZEWSKI, J. T.、ALLEN, R. C.、GARDNER, B. A.、SCHMID, B. L.、STACHE, U.、+

  DOI：——

  日期：——
• Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles
  作者：Joseph T. Strupczewski、Richard C. Allen、Beth Ann Gardner、Blaine L. Schmid、Ulrich Stache、Edward J. Glamkowski、Michael C. Jones、Daniel B. Ellis、Francis P. Huger、Robert W. Dunn

  DOI：10.1021/jm00383a012

  日期：1985.6

  The synthesis of a series of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles is described. The neuroleptic activity of the series was evaluated by utilizing the climbing mice assay and inhibition of [3H]spiroperidol binding. Structure-activity relationships were studied by variation of the substituent on the benzisoxazole ring with concomitant variation of four different 1-piperidinyl substituents. Maximum neuroleptic activity was realized when there was a 6-fluoro substituent on the benzisoxazole ring. The 1-piperidinyl substituent appeared less significant, although in most cases, the (1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl group imparted maximum potency. The most potent compound in both assays was 6-fluoro-3-[1-[3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl) propyl]-4-piperidinyl]-1,2-benzisoxazole (11b).