1-bromo-2,2-dimethoxyheptane | 129620-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-2,2-dimethoxyheptane
• 英文别名: 1-bromo-heptan-2-one-dimethylacetal；1-Brom-2.2-dimethoxy-heptan；1-Brom-heptan-2-on-dimethylacetal
• CAS: 129620-22-0
• 化学式: C₉H₁₉BrO₂
• 分子量: 239.153
• InChiKey: FIUPYDQQGHSXFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1-bromo-2,2-dimethoxyheptane 在 sodium hydroxide 、 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 87.67h， 生成 -(3-butyl-6-methoxy-2-benzothiophene-yl)-N-<1-methyl-4-(3-pyridinyl)butyl>-2-propenamide
  参考文献：
  名称：

  Propenyl carboxamide derivatives as antagonists of platelet-activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl] 3-substituted propenyl carboxamide derivatives bearing an unsaturated bicyclic moiety in the 3-position was prepared and evaluated for PAF (platelet activating factor) antagonist activity. These compounds represent conformationally constrained direct analogues of the corresponding potent 5-aryl-pentadienecarboxamides (5). Most of the new compounds were active in a PAF-binding assay employing whole, washed dog platelets as the receptor source and inhibited PAF-induced bronchoconstriction in guinea pigs after intravenous administration. However, oral activity in the PAF-induced bronchoconstriction model was highly sensitive to the nature and substitution of the bicyclic ring system. The most interesting compounds included [R-(E)]-(1-butyl-6-methoxy-2-naphthyl)-N-[1-methyl-4-(3- pyridinyl)butyl]-2-propenamide (4b), [R-(E)]-(3-butyl-6-methoxy-2- benzo[b]thiophene-yl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide (4k), and [R-(E)]-(3-butyl-6-methoxy-1-methyl-2-indoly)-N-[1-ethyl-4- (3-pyridinyl)butyl]-2-propenamide (4l) which inhibited PAF-induced broncho-constriction in guinea pigs with IC50s of 3.0-5.4 mg/kg, when the animals were challenged 2 h after drug treatment. They were also highly effective 6 h after a 50 mg/kg oral dose. This study supports the notion that the key remote aromatic ring present in the 5-arylpentadienecarboxamides (5) is preferentially coplanar with the diene system for good PAF antagonist activity.

  DOI：

  10.1021/jm00172a029
• 作为产物：
  描述：

  magnesium,hept-1-yne,bromide 在 乙醚 、 三氟化硼乙醚 、 溴 、 mercury(II) oxide 作用下， 生成 1-bromo-2,2-dimethoxyheptane
  参考文献：
  名称：

  McCusker; Vogt, Journal of the American Chemical Society, 1937, vol. 59, p. 1309

  摘要：

  DOI：

文献信息

• GUTHRIE, ROBERT W.;KAPLAN, GERALD L.;MENNONA, FRANCIS A.;TILLEY, JEFFERSO+, J. MED. CHEM., 33,(1990) N0, C. 2856-2864
  作者：GUTHRIE, ROBERT W.、KAPLAN, GERALD L.、MENNONA, FRANCIS A.、TILLEY, JEFFERSO+

  DOI：——

  日期：——
• Propenyl carboxamide derivatives as antagonists of platelet-activating factor
  作者：Robert W. Guthrie、Gerald L. Kaplan、Francis A. Mennona、Jefferson W. Tilley、Richard W. Kierstead、Margaret O'Donnell、Herman Crowley、Bohdan Yaremko、Ann F. Welton

  DOI：10.1021/jm00172a029

  日期：1990.10

  A series of N-[4-(3-pyridinyl)butyl] 3-substituted propenyl carboxamide derivatives bearing an unsaturated bicyclic moiety in the 3-position was prepared and evaluated for PAF (platelet activating factor) antagonist activity. These compounds represent conformationally constrained direct analogues of the corresponding potent 5-aryl-pentadienecarboxamides (5). Most of the new compounds were active in a PAF-binding assay employing whole, washed dog platelets as the receptor source and inhibited PAF-induced bronchoconstriction in guinea pigs after intravenous administration. However, oral activity in the PAF-induced bronchoconstriction model was highly sensitive to the nature and substitution of the bicyclic ring system. The most interesting compounds included [R-(E)]-(1-butyl-6-methoxy-2-naphthyl)-N-[1-methyl-4-(3- pyridinyl)butyl]-2-propenamide (4b), [R-(E)]-(3-butyl-6-methoxy-2- benzo[b]thiophene-yl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide (4k), and [R-(E)]-(3-butyl-6-methoxy-1-methyl-2-indoly)-N-[1-ethyl-4- (3-pyridinyl)butyl]-2-propenamide (4l) which inhibited PAF-induced broncho-constriction in guinea pigs with IC50s of 3.0-5.4 mg/kg, when the animals were challenged 2 h after drug treatment. They were also highly effective 6 h after a 50 mg/kg oral dose. This study supports the notion that the key remote aromatic ring present in the 5-arylpentadienecarboxamides (5) is preferentially coplanar with the diene system for good PAF antagonist activity.
• McCusker; Vogt, Journal of the American Chemical Society, 1937, vol. 59, p. 1309
  作者：McCusker、Vogt

  DOI：——

  日期：——