2-allyl-6-benzylimino-4-methylene-2-azaspiro[4.4]nonan-1-one | 152252-72-7

• 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: 2-allyl-6-benzylimino-4-methylene-2-azaspiro[4.4]nonan-1-one
• 英文别名: 9-Benzylimino-4-methylidene-2-prop-2-enyl-2-azaspiro[4.4]nonan-1-one
• CAS: 152252-72-7
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: TUTQWRQTYHISHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-allyl-6-benzylimino-4-methylene-2-azaspiro[4.4]nonan-1-one 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 以90%的产率得到2-allyl-4-methylene-2-azaspiro[4.4]nonane-1,6-dione
  参考文献：
  名称：

  Metallic Salt Promoted Radical Cyclization of β-Keto Carboxamides and Their Corresponding β-Enamino Carboxamides

  摘要：

  Substituted lactams and spirolactams were obtained by Mn(III)-induced radical cyclization of unsaturated beta -keto carboxamides. Treatment of the corresponding tertiary enamines under similar reaction conditions and in the presence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines leads to diastereomeric spirolactams in an approximately 3:1 ratio.

  DOI：

  10.1021/jo000084u
• 作为产物：
  描述：

  2-oxo-cyclopentanecarboxylic acid diallylamide 在 copper diacetate 、 3 A molecular sieve 、 manganese triacetate 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 48.0h， 生成 2-allyl-6-benzylimino-4-methylene-2-azaspiro[4.4]nonan-1-one
  参考文献：
  名称：

  Metallic Salt Promoted Radical Cyclization of β-Keto Carboxamides and Their Corresponding β-Enamino Carboxamides

  摘要：

  Substituted lactams and spirolactams were obtained by Mn(III)-induced radical cyclization of unsaturated beta -keto carboxamides. Treatment of the corresponding tertiary enamines under similar reaction conditions and in the presence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines leads to diastereomeric spirolactams in an approximately 3:1 ratio.

  DOI：

  10.1021/jo000084u

文献信息

• Generation of radical cations from enamines and their addition to unactivated olefins
  作者：Janine Cossy、Abderrahim Bouzide

  DOI：10.1039/c39930001218

  日期：——

  Oxidation of unsaturated enamines by metallic salts produced radical cations which added intramolecularly to unactivated olefins, producing cyclized products in a highly efficient manner.

  不饱和烯胺在金属盐的作用下发生氧化，生成自由基阳离子，这些阳离子在分子内与未活化的烯烃结合，以高效的方式生成环状产物。
• Metallic Salt Promoted Radical Cyclization of β-Keto Carboxamides and Their Corresponding β-Enamino Carboxamides
  作者：Janine Cossy、Abderrahim Bouzide、Catherine Leblanc

  DOI：10.1021/jo000084u

  日期：2000.11.1

  Substituted lactams and spirolactams were obtained by Mn(III)-induced radical cyclization of unsaturated beta -keto carboxamides. Treatment of the corresponding tertiary enamines under similar reaction conditions and in the presence of K2CO3 afforded the same cyclized products but with inversion of diastereoselectivity. The oxidation of optically pure secondary enamines leads to diastereomeric spirolactams in an approximately 3:1 ratio.