5-(benzyloxy)-4-methoxy-2-nitrotoluene | 2495-83-2

• 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: 5-(benzyloxy)-4-methoxy-2-nitrotoluene
• 英文别名: 2-Nitro-4-methoxy-5-benzyloxy-toluol；5-Benzyloxy-4-methoxy-2-nitro-toluol；6-Nitro-4-methoxy-3-benzyloxy-toluol；1-Methoxy-4-methyl-5-nitro-2-phenylmethoxybenzene
• CAS: 2495-83-2
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: AGBPKBAXTFDOAM-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: ethanol (64-17-5))
• 沸点：
  428.8±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-4-methoxy-2-nitrotoluene 在 palladium on activated charcoal 盐酸 、 乙醇 、 氢气 、 sodium 、 溶剂黄146 作用下， 50.0~78.0 ℃ 、310.27 kPa 条件下， 反应 0.17h， 生成 (RS)-1-<2-amino-5-(benzyloxy)-4-methoxybenzyl>-2-methyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride
  参考文献：
  名称：

  Isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") as possible products of metabolism by catechol-O-methyltransferase

  摘要：

  The isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine (''isoapomorphine'') were synthesized unequivocally as possible metabolites in catechol-O-methyltransferase (COMT) mediated O-methylation reactions. In vitro incubation studies revealed that isoapomorphine is not a substrate for the COMT using experimental conditions under which apomorphine (10,11-dihydroxyaporphine) is converted in high yield into its 10-methyl ether, apocodeine. The in vivo dopaminergic inactivity of isoapomorphine (as compared with that of apomorphine) seems to be due to factors other than metabolic inactivation by COMT.

  DOI：

  10.1021/jm00107a030
• 作为产物：
  描述：

  2-甲氧基-5-甲基苯酚 在 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-(benzyloxy)-4-methoxy-2-nitrotoluene
  参考文献：
  名称：

  Isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") as possible products of metabolism by catechol-O-methyltransferase

  摘要：

  The isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine (''isoapomorphine'') were synthesized unequivocally as possible metabolites in catechol-O-methyltransferase (COMT) mediated O-methylation reactions. In vitro incubation studies revealed that isoapomorphine is not a substrate for the COMT using experimental conditions under which apomorphine (10,11-dihydroxyaporphine) is converted in high yield into its 10-methyl ether, apocodeine. The in vivo dopaminergic inactivity of isoapomorphine (as compared with that of apomorphine) seems to be due to factors other than metabolic inactivation by COMT.

  DOI：

  10.1021/jm00107a030

文献信息

• Pasini,C. et al., Gazzetta Chimica Italiana, 1963, vol. 93, p. 1056 - 1065
  作者：Pasini,C. et al.

  DOI：——

  日期：——
• CANNON, JOSEPH G.;QIJIE, PANG, J. MED. CHEM., 34,(1991) N, C. 1079-1082
  作者：CANNON, JOSEPH G.、QIJIE, PANG

  DOI：——

  日期：——
• Isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine ("isoapomorphine") as possible products of metabolism by catechol-O-methyltransferase
  作者：Joseph G. Cannon、Pang Qijie

  DOI：10.1021/jm00107a030

  日期：1991.3

  The isomeric monomethyl ether derivatives of (RS)-9,10-dihydroxyaporphine (''isoapomorphine'') were synthesized unequivocally as possible metabolites in catechol-O-methyltransferase (COMT) mediated O-methylation reactions. In vitro incubation studies revealed that isoapomorphine is not a substrate for the COMT using experimental conditions under which apomorphine (10,11-dihydroxyaporphine) is converted in high yield into its 10-methyl ether, apocodeine. The in vivo dopaminergic inactivity of isoapomorphine (as compared with that of apomorphine) seems to be due to factors other than metabolic inactivation by COMT.