2-ethoxycarbonyl-1-methyl-5-vinyl-2,3,6,7-tetrahydrodiazepine | 72686-88-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-ethoxycarbonyl-1-methyl-5-vinyl-2,3,6,7-tetrahydrodiazepine
• 英文别名: 5-Vinyl-1,2,5,6-tetrahydro-1,2-diazepin；ethyl 5-ethenyl-2-methyl-4,7-dihydro-3H-diazepine-1-carboxylate
• CAS: 72686-88-5
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: KBUCWSAVMLXPAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-methyl-4-vinyl-ethoxycarbonylimino-1,2,5,6-tetrahydropyridinium ylide 以24%的产率得到
  参考文献：
  名称：

  TSUCHIYA, TAKASHI;SASHIDA, HARUKI, CHEM. AND PHARM. BULL., 1981, 29, N 7, 1887-1892

  摘要：

  DOI：

文献信息

• Thermal rearrangements of cyclic amine ylides. II. Ring-expansion of 4-and 6-vinyl-1,2,5,6-tetrahydropyridine and 2-vinylpiperidine N-imides.
  作者：TAKASHI TSUCHIYA、HARUKI SASHIDA

  DOI：10.1248/cpb.29.1887

  日期：——

  The thermolysis of the 4-vinyl-1, 2, 5, 6-tetrahydropyridine N-imide (13a) resulted in both [1, 2-]- and [2, 3]-sigmatropic rearrangements to give the tetrahydro-1, 2-diazepine (18) and the 3, 3-divinyltetrahydropyrazole (19), respectively ; this reaction mechanism was confirmed by a deuterium-labelling experiment. In contrast, the thermolysis of both 6-vinyl-1, 2, 5, 6-tetrahydropyridine N-imide (13b) and 2-vinylpiperidine N-imide (17) resulted in only [2, 3] rearrangement with the vinyl group to give nine-membered ring products, the tetrahydro- (21) and the hexahydro-1, 2-diazonine (25), respectively. The starting vinyltetrahydropyridine N-imides (13a, b) were prepared from the corresponding vinylpyridines (10a, b), and 2-vinylpiperidine N-imide (17) was prepared from 1-ethoxycarbonyl-2-vinylpiperidine (14).

  4-vinyl-1, 2, 5, 6-四氢吡啶 N-亚胺（13a）的热分解导致[1, 2]-和[2, 3]-异构重排，分别生成四氢-1, 2-二氮杂卓（18）和 3, 3-二乙烯基四氢吡唑（19）；氘标记实验证实了这一反应机理。相反，6-乙烯基-1，2，5，6-四氢吡啶 N-酰亚胺（13b）和 2-乙烯基哌啶 N-酰亚胺（17）在热分解过程中只与乙烯基发生[2，3]重排反应，生成九元环产物，分别是四氢-（21）和六氢-1，2-二氮杂吲哚（25）。起始乙烯基四氢吡啶 N-亚胺（13a、b）由相应的乙烯基吡啶（10a、b）制备，2-乙烯基哌啶 N-亚胺（17）由 1-乙氧羰基-2-乙烯基哌啶（14）制备。