4-氰基-4-(间甲氧基苯基)戊酸甲酯 | 100189-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-氰基-4-(间甲氧基苯基)戊酸甲酯
• 英文名称: methyl 4-cyano-4-(m-methoxyphenyl)pentanoate
• 英文别名: 4-Cyan-4-<3-Methoxy-phenyl>-pentansaeure-(1)-methylester；Methyl-γ-cyano-γ-(m-methoxyphenyl)valerat；4-Cyan-4-(3-Methoxy-phenyl)-pentansaeure-(1)-methylester；Methyl 4-cyano-4-(3-methoxyphenyl)pentanoate
• CAS: 100189-40-0
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: QEFPUEZVITZXKB-UHFFFAOYSA-N

物化性质

• 沸点：
  145-153 °C(Press: 0.35 Torr)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氰基-4-(间甲氧基苯基)戊酸甲酯 在 platinum(IV) oxide 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 diborane(6) 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 25.0 ℃ 、434.37 kPa 条件下， 反应 60.0h， 生成 1,3-dimethyl-3-(m-methoxyphenyl)piperidine
  参考文献：
  名称：

  N-Substituent modulation of opiate agonist/antagonist activity in resolved 3-methyl-3-(m-hydroxyphenyl)piperidines

  摘要：

  A series of 3-methyl-3-(m-hydroxyphenyl)piperidines with N-substituent variations have been synthesized and resolved, and an X-ray crystal structure of one analogue was determined. The compounds have been characterized, pharmacologically, by detailed opiate receptor binding studies and determination of in vivo analgesia and opiate antagonism. The results indicate that all compounds bind with high selectivity and moderate affinity to mu-receptors with no qualitative difference between enantiomeric pairs. By contrast a striking difference in activities is found, with the (-) enantiomers being pure agonists and the (+) enantiomers having both agonist and antagonist activity. The effect of N-substituents on relative agonist and antagonist potency does not mimic that of fused ring opiates with the N-phenethyl compound, the most potent antagonist. These results together with the X-ray structure obtained suggest that agonist and antagonist activity is initiated by a bimodel binding of the compounds in two different orientations at the mu-receptor site.

  DOI：

  10.1021/jm00154a018
• 作为产物：
  描述：

  2-(3-甲氧基苯基)丙腈 、 丙烯酸甲酯（MA） 在 苄基三甲基氢氧化铵 作用下， 以 1,4-二氧六环 为溶剂， 以92%的产率得到4-氰基-4-(间甲氧基苯基)戊酸甲酯
  参考文献：
  名称：

  N-Substituent modulation of opiate agonist/antagonist activity in resolved 3-methyl-3-(m-hydroxyphenyl)piperidines

  摘要：

  A series of 3-methyl-3-(m-hydroxyphenyl)piperidines with N-substituent variations have been synthesized and resolved, and an X-ray crystal structure of one analogue was determined. The compounds have been characterized, pharmacologically, by detailed opiate receptor binding studies and determination of in vivo analgesia and opiate antagonism. The results indicate that all compounds bind with high selectivity and moderate affinity to mu-receptors with no qualitative difference between enantiomeric pairs. By contrast a striking difference in activities is found, with the (-) enantiomers being pure agonists and the (+) enantiomers having both agonist and antagonist activity. The effect of N-substituents on relative agonist and antagonist potency does not mimic that of fused ring opiates with the N-phenethyl compound, the most potent antagonist. These results together with the X-ray structure obtained suggest that agonist and antagonist activity is initiated by a bimodel binding of the compounds in two different orientations at the mu-receptor site.

  DOI：

  10.1021/jm00154a018

文献信息

• CHENG, A.;UVENO, E.;POLGAR, W.;TOLL, L.;LAWSON, J. A.;DE, GRAW, J. I.;LOE+, J. MED. CHEM., 1986, 29, N 4, 531-537
  作者：CHENG, A.、UVENO, E.、POLGAR, W.、TOLL, L.、LAWSON, J. A.、DE, GRAW, J. I.、LOE+

  DOI：——

  日期：——