3'-hydroxynornicotine | 75195-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3'-hydroxynornicotine
• 英文别名: 2-Pyridin-3-ylpyrrolidin-3-ol
• CAS: 75195-79-8
• 化学式: C₉H₁₂N₂O
• 分子量: 164.207
• InChiKey: HHHLLLHJUHIVTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-hydroxynornicotine 在 sodium nitrite 作用下， 以 水 为溶剂， 反应 16.0h， 以50%的产率得到3'-hydroxy-N'-nitrosonornicotine
  参考文献：
  名称：

  Metabolic .beta.-hydroxylation and N-oxidation of n'-nitrosonornicotine

  摘要：

  3'-Hydroxy-N'-nitrosonornicotine (2), 4'-hydroxy-N'-nitrosonornicotine (3), N'-nitrosonornicotine 1-N-oxide (4) were synthesized and identified as metabolites in the F-344 rat of the tobacco-specific carcinogen N'-nitrosonornicotine (1). For the synthesis of 2, myosmine (5) was converted to 3'-bromomyosmine (6). Displacement by acetate and hydrolysis gave 3'-hydroxymyosmine (7), which was reduced and nitrosated to give 2. 4'-Hydroxymyosmine (13), the precursor to 3, was prepared by ammonolysis of 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane (10). N'-Nitrosonornicotine 1-N-oxide (4) was prepared by m-chloroperbenzoic acid oxidation of 1. When 1 was incubated with liver microsomes from Aroclor-pretreated F-344 rats, trace amounts of 2 and 3 were produced and 4 was a major metabolite. The urine from rats treated with N'-nitrosonornicotine-2'-14C contained only trace amounts of 2 and 3, whereas 4 accounted for 6.7-9.4% of the dose.

  DOI：

  10.1021/jm00185a005
• 作为产物：
  描述：

  麦司明 在 sodium hydroxide 、 sodium tetrahydroborate 、 silver(I) acetate 、 phenyltrimethylammonium tribromide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 3'-hydroxynornicotine
  参考文献：
  名称：

  Metabolic .beta.-hydroxylation and N-oxidation of n'-nitrosonornicotine

  摘要：

  3'-Hydroxy-N'-nitrosonornicotine (2), 4'-hydroxy-N'-nitrosonornicotine (3), N'-nitrosonornicotine 1-N-oxide (4) were synthesized and identified as metabolites in the F-344 rat of the tobacco-specific carcinogen N'-nitrosonornicotine (1). For the synthesis of 2, myosmine (5) was converted to 3'-bromomyosmine (6). Displacement by acetate and hydrolysis gave 3'-hydroxymyosmine (7), which was reduced and nitrosated to give 2. 4'-Hydroxymyosmine (13), the precursor to 3, was prepared by ammonolysis of 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane (10). N'-Nitrosonornicotine 1-N-oxide (4) was prepared by m-chloroperbenzoic acid oxidation of 1. When 1 was incubated with liver microsomes from Aroclor-pretreated F-344 rats, trace amounts of 2 and 3 were produced and 4 was a major metabolite. The urine from rats treated with N'-nitrosonornicotine-2'-14C contained only trace amounts of 2 and 3, whereas 4 accounted for 6.7-9.4% of the dose.

  DOI：

  10.1021/jm00185a005

文献信息

• HECHT S. S.; CHEN CHI-HONG B.; HOFFMANN D., J. MED. CHEM., 1980, 23, NO 11, 1175-1178
  作者：HECHT S. S.、 CHEN CHI-HONG B.、 HOFFMANN D.

  DOI：——

  日期：——
• Metabolic .beta.-hydroxylation and N-oxidation of n'-nitrosonornicotine
  作者：Stephen S. Hecht、Chi-Hong B. Chen、Dietrich Hoffmann

  DOI：10.1021/jm00185a005

  日期：1980.11

  3'-Hydroxy-N'-nitrosonornicotine (2), 4'-hydroxy-N'-nitrosonornicotine (3), N'-nitrosonornicotine 1-N-oxide (4) were synthesized and identified as metabolites in the F-344 rat of the tobacco-specific carcinogen N'-nitrosonornicotine (1). For the synthesis of 2, myosmine (5) was converted to 3'-bromomyosmine (6). Displacement by acetate and hydrolysis gave 3'-hydroxymyosmine (7), which was reduced and nitrosated to give 2. 4'-Hydroxymyosmine (13), the precursor to 3, was prepared by ammonolysis of 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane (10). N'-Nitrosonornicotine 1-N-oxide (4) was prepared by m-chloroperbenzoic acid oxidation of 1. When 1 was incubated with liver microsomes from Aroclor-pretreated F-344 rats, trace amounts of 2 and 3 were produced and 4 was a major metabolite. The urine from rats treated with N'-nitrosonornicotine-2'-14C contained only trace amounts of 2 and 3, whereas 4 accounted for 6.7-9.4% of the dose.