(4S,5S)-2-Allyl-4-methyl-2-aza-spiro[4.4]nonane-1,6-dione | 126863-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5S)-2-Allyl-4-methyl-2-aza-spiro[4.4]nonane-1,6-dione
• 英文别名: (4R,5R)-2-Allyl-4-methyl-2-aza-spiro[4.4]nonane-1,6-dione；2-allyl-4-methyl-2-azaspiro[4.4]nonane-1,6-dione
• CAS: 126863-03-4；126863-04-5；144179-01-1；144179-02-2
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: UATSEHMJDMNRTD-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-Benzylamino-cyclopent-1-enecarboxylic acid diallylamide 在 manganese triacetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (4S,5S)-2-Allyl-4-methyl-2-aza-spiro[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

文献信息

• Intramolecular Ene Reactions. Stereo- and Enantioselective Synthesis of Spirolactams through Thermolysis of Enamino Carboxamides
  作者：Janine Cossy、Abdelrrahim Bouzide、Michel Pfau

  DOI：10.1021/jo970257o

  日期：1997.10.1

  thermal rearrangement of tertiary and secondary enamino carboxamides has been developed. The enamine group of an enamino carboxamide, in which no electron-withdrawing group is present in the enophile, can be involved in the ene reaction and the enamino carboxamide can be transformed into enamino or imino spirolactams. In the case of secondary carboxamido enamines, the diastereoselectivity is higher than 98%

  基于叔和仲烯氨基羧酰胺的热重排，已经开发了一种新的，容易获得螺内酰胺的方法。烯反应中不存在吸电子基的烯氨基羧酰胺的烯胺基可以参与烯反应，并且烯氨基羧酰胺可以转化为烯氨基或亚氨基螺内酰胺。在仲羧酰胺烯胺的情况下，非对映选择性高于98％。如果使用手性非外消旋类似物，则最终产物中对映体过量可达到50-54％。
• Stereoselective formation of spirolactams by intramolecular ene reaction
  作者：J. Cossy、A. Bouzide

  DOI：10.1016/s0040-4039(00)92226-3

  日期：1992.4

  A new and facile access to spirolactams based on the thermal rearrangements of N,N-unsaturated dialkyl-β-ketoamides and N,N-unsaturated dialkyl enaminoamides has been developed.

  基于N，N-不饱和二烷基-β-酮酰胺和N，N-不饱和二烷基烯酰胺的热重排，已经开发了一种新的容易获得螺内酰胺的方法。
• Thermolysis of N-unsaturated alkyl-β-ketoamides. An easy access to spirolactams
  作者：Janine Cossy、Abderrahim Bouzide

  DOI：10.1016/s0040-4020(97)00262-7

  日期：1997.4

  A facile access to spirolactams based on the thermal rearrangement of N,N-unsaturated dialkyl- and of N-unsaturated alkyl-N-alkyl-beta-ketoamides is presented. (C) 1997 Elsevier Science Ltd.