ethyl 3-(methylamino)-4-phenylbutyrate | 60546-98-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-(methylamino)-4-phenylbutyrate
• 英文别名: 3-Methylamino-4-phenyl-buttersaeure-ethylester；Ethyl 3-(methylamino)-4-phenylbutanoate
• CAS: 60546-98-7
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: FHASYLFULHDNMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(methylamino)-4-phenylbutyrate 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢氟酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 37.0h， 生成 N-(cyclopropylmethyl)-4-methoxy-N-methyl-4-phenyl-2,3-dihydro-1H-naphthalen-2-amine
  参考文献：
  名称：

  Aminotetralins as narcotic antagonists. 2. Synthesis and opiate-related activity of 1-phenyl-3-aminotetralins

  摘要：

  The synthesis and analgetic agonist and antagonist activities of several 3-[N-(cyclopropylmethyl)-N-methylamino]-1-phenyltetralins are reported. The design of these agents was based partially on the possibility of two aryl receptor binding sites on the opiate receptor. The agents lack the phenolic hydroxyl and quaternary carbon functionalities generally associated with opiate activity; yet both the cis- and trans-1-phenyl-3-aminotetralins displayed significant agonist and antagonist activity. In preliminary studies, the trans isomer neither suppressed nor precipitated withdrawal signs in addicted monkeys.

  DOI：

  10.1021/jm00345a005
• 作为产物：
  描述：

  4-苯基乙酰乙酸乙酯 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 ethyl 3-(methylamino)-4-phenylbutyrate
  参考文献：
  名称：

  Aminotetralins as narcotic antagonists. 2. Synthesis and opiate-related activity of 1-phenyl-3-aminotetralins

  摘要：

  The synthesis and analgetic agonist and antagonist activities of several 3-[N-(cyclopropylmethyl)-N-methylamino]-1-phenyltetralins are reported. The design of these agents was based partially on the possibility of two aryl receptor binding sites on the opiate receptor. The agents lack the phenolic hydroxyl and quaternary carbon functionalities generally associated with opiate activity; yet both the cis- and trans-1-phenyl-3-aminotetralins displayed significant agonist and antagonist activity. In preliminary studies, the trans isomer neither suppressed nor precipitated withdrawal signs in addicted monkeys.

  DOI：

  10.1021/jm00345a005

文献信息

• FRIES, D. S.;BERTELLI, D. J., J. MED. CHEM., 1982, 25, N 3, 216-220
  作者：FRIES, D. S.、BERTELLI, D. J.

  DOI：——

  日期：——
• Aminotetralins as narcotic antagonists. 2. Synthesis and opiate-related activity of 1-phenyl-3-aminotetralins
  作者：David S. Fries、Dominick J. Bertelli

  DOI：10.1021/jm00345a005

  日期：1982.3

  The synthesis and analgetic agonist and antagonist activities of several 3-[N-(cyclopropylmethyl)-N-methylamino]-1-phenyltetralins are reported. The design of these agents was based partially on the possibility of two aryl receptor binding sites on the opiate receptor. The agents lack the phenolic hydroxyl and quaternary carbon functionalities generally associated with opiate activity; yet both the cis- and trans-1-phenyl-3-aminotetralins displayed significant agonist and antagonist activity. In preliminary studies, the trans isomer neither suppressed nor precipitated withdrawal signs in addicted monkeys.