2,2-dimethyl-6-(1-methyl-1-methylselanylethyl)hexahydropyrrolizin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: 2,2-dimethyl-6-(1-methyl-1-methylselanylethyl)hexahydropyrrolizin-3-one
• 英文别名: 2,2-dimethyl-6-(2-phenylselanylpropan-2-yl)-5,6,7,8-tetrahydro-1H-pyrrolizin-3-one
• 化学式: C₁₈H₂₅NOSe
• 分子量: 350.363
• InChiKey: AZFQUPRGJFMDHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2-dimethylpent-4-enoyl chloride 在 吡啶 、 叔丁基亚磺酰氯 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2,2-dimethyl-6-(1-methyl-1-methylselanylethyl)hexahydropyrrolizin-3-one
  参考文献：
  名称：

  Development of efficient new methodology for generation, cyclization and functional trapping of iminyl and amidyl radicals

  摘要：

  New methodology has been devised for the generation and subsequent cyclization of iminyl and amidyl radicals under mild conditions. The process involves either the treatment of oximes with 2,6-dimethylbenzenesulfinyl chloride, or the treatment of hydroxamic acids with tert-butylsulfinyl chloride (-50 degreesC to rt), to give the corresponding nitrogen radicals, followed by cyclization onto pendant olefins. Radical traps such as diphenyl diselenide, diphenyl disulfide, and TEMPO can be used to terminate the cyclizations, thus introducing functionality that provides multiple options for further manipulation. In a more convenient procedure, both iminyl and amidyl radical cyclizations can be initiated using commercially available diethyl chlorophosphite which generally provides similar (with diphenyl disulfide and TEMPO) or significantly higher (with diphenyl diselenide) yields of products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00878-x

文献信息

• A mild new procedure for production, cyclization and trapping of amidyl radicals: application to a formal total synthesis of peduncularine
  作者：Xichen Lin、Didier Stien、Steven M Weinreb

  DOI：10.1016/s0040-4039(00)00194-5

  日期：2000.4

  TEMPO affords a functionalized product derived from an amidyl radical cyclization. The methodology has been used in a formal total synthesis of the 6-azabicyclo[3.2.1]octane-containing indole alkaloid peduncularine.

  在自由基捕集剂（例如二苯基二硒化物，二苯基二硫化物或TEMPO）的存在下，在-50°C至室温下用叔丁基亚磺酰氯和Hunig碱处理烯属异羟肟酸，可得自酰胺基自由基环化的官能化产物。该方法已用于含6-氮杂双环[3.2.1]辛烷的吲哚生物碱peduncularine的正式全合成中。