4-chloromethyl-1,2-dipropoxy-benzene | 100620-61-9

• 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: 4-chloromethyl-1,2-dipropoxy-benzene
• 英文别名: 4-Chlormethyl-1,2-dipropoxy-benzol；4-(Chloromethyl)-1,2-dipropoxybenzene
• CAS: 100620-61-9
• 化学式: C₁₃H₁₉ClO₂
• 分子量: 242.746
• InChiKey: WBFFNPFVKVTZLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloromethyl-1,2-dipropoxy-benzene 、 3-氮杂双环[2.2.2]辛烷盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3,4-di-n-propyloxybenzyl)isoquinuclidine hydrochloride
  参考文献：
  名称：

  Isoquinuclidine-based expectorants. Synthesis and biological activities of N-alkoxybenzylisoquinuclidines

  摘要：

  N-Di-, trialkoxybenzylisoquinuclidines and related compounds were synthesized and evaluated for expectorant activities. Structure-activity relationship investigations in this series showed that both the trialkoxyphenyl ring and the basic nitrogen atom at the benzylic position were necessary for activity. N-Trialkoxybenzylisoquinuclidines 7a, 7c, 7d, 7f and 7g significantly increased bronchial secretion, and ethoxy derivative 7c showed the highest activity in these compounds. The n-propyloxy derivatives 7d and 7f also accelerated bronchoalveolar surfactant secretion with about two to four times more activity than ambroxol (7d and 7f; ED50 = 27.5 and 15.5 mg/kg po, respectively); however, compounds 7a, 7c and 7g were less active than ambroxol. Compounds 7d and 7f were selected for further examination. These compounds displayed antioxidant activity in vitro (7d and 7f, IC50 = 48.0 and 66.0 mu M, respectively). Compound 7d also showed inhibition on bradykinin- or antigen-induced airway inflammation in guinea pigs. These findings suggest that compounds 7d and 7f are potent expectorants with antiinflammatory activity.

  DOI：

  10.1016/s0223-5234(97)81675-3
• 作为产物：
  描述：

  聚合甲醛 、 1,2-二正丙氧基苯 在 盐酸 、 磷酸 、 溶剂黄146 、 汞 作用下， 生成 4-chloromethyl-1,2-dipropoxy-benzene
  参考文献：
  名称：

  Mel'nikow; Priluzkaja, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3746,3747; engl. Ausg. S. 3704, 3705

  摘要：

  DOI：

文献信息

• Isoquinuclidine-based expectorants. Synthesis and biological activities of N-alkoxybenzylisoquinuclidines
  作者：M Yokota、E Takizawa、Y Ohkura、C Fukai、T Tomiyama

  DOI：10.1016/s0223-5234(97)81675-3

  日期：1997.5

  N-Di-, trialkoxybenzylisoquinuclidines and related compounds were synthesized and evaluated for expectorant activities. Structure-activity relationship investigations in this series showed that both the trialkoxyphenyl ring and the basic nitrogen atom at the benzylic position were necessary for activity. N-Trialkoxybenzylisoquinuclidines 7a, 7c, 7d, 7f and 7g significantly increased bronchial secretion, and ethoxy derivative 7c showed the highest activity in these compounds. The n-propyloxy derivatives 7d and 7f also accelerated bronchoalveolar surfactant secretion with about two to four times more activity than ambroxol (7d and 7f; ED50 = 27.5 and 15.5 mg/kg po, respectively); however, compounds 7a, 7c and 7g were less active than ambroxol. Compounds 7d and 7f were selected for further examination. These compounds displayed antioxidant activity in vitro (7d and 7f, IC50 = 48.0 and 66.0 mu M, respectively). Compound 7d also showed inhibition on bradykinin- or antigen-induced airway inflammation in guinea pigs. These findings suggest that compounds 7d and 7f are potent expectorants with antiinflammatory activity.
• Mel'nikow; Priluzkaja, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3746,3747; engl. Ausg. S. 3704, 3705
  作者：Mel'nikow、Priluzkaja

  DOI：——

  日期：——