3-Butyl-5-methyloctahydroindolizin | 53447-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: 3-Butyl-5-methyloctahydroindolizin
• 英文别名: (3R,5R,8aS)-3-butyl-5-methyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• CAS: 53447-43-1
• 化学式: C₁₃H₂₅N
• 分子量: 195.348
• InChiKey: HFUFMWLNHRIKMV-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (4R)-4-氨基戊酸 在 rhodium on alumina 劳森试剂 、 lithium aluminium tetrahydride 、 W-2 Raney nickel 、 四丁基氯化铵 、 氢气 、 双氧水 、 sodium acetate 、 iron(II) sulfate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 40.0 ℃ 、379.21 kPa 条件下， 反应 103.33h， 生成 3-Butyl-5-methyloctahydroindolizin
  参考文献：
  名称：

  Oxidative Radical Cyclization of (.omega.-Iodoalkyl)indoles and Pyrroles. Synthesis of (-)-Monomorine and Three Diastereomers

  摘要：

  Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H(2)O (1 equiv) in Dh ISO containing the N-(omega-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (omega-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H-2/Rh-A1(2)O(3)), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58 (see, however, Note Added in Proof).

  DOI：

  10.1021/jo00088a029

文献信息

• Oxidative Radical Cyclization of (.omega.-Iodoalkyl)indoles and Pyrroles. Synthesis of (-)-Monomorine and Three Diastereomers
  作者：Dean R. Artis、In-Seop Cho、Saul Jaime-Figueroa、Joseph M. Muchowski

  DOI：10.1021/jo00088a029

  日期：1994.5

  Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H(2)O (1 equiv) in Dh ISO containing the N-(omega-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (omega-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H-2/Rh-A1(2)O(3)), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58 (see, however, Note Added in Proof).