4,4-dimethyl-2-phenylselanylmethyl-3,4-dihydro-2H-pyrrole | 240426-73-7

• 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: 4,4-dimethyl-2-phenylselanylmethyl-3,4-dihydro-2H-pyrrole
• 英文别名: 4,4-dimethyl-2-phenylselenylmethyl-3,4-dihydro-2H-pyrrole；4,4-Dimethyl-2-[(phenylselanyl)methyl]-3,4-dihydro-2H-pyrrole；4,4-dimethyl-2-(phenylselanylmethyl)-2,3-dihydropyrrole
• CAS: 240426-73-7
• 化学式: C₁₃H₁₇NSe
• 分子量: 266.245
• InChiKey: HDEQZHJVZVAWHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-phenylselanylmethyl-3,4-dihydro-2H-pyrrole 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 以89%的产率得到4,4-dimethyl-2-[(phenylseleno)methyl]pyrrolidine
  参考文献：
  名称：

  亲电试剂诱导的烯基亚磺胺和烯基亚磺酰胺的环化反应和伴随的N-脱保护，作为直接通往环状或螺环亚胺，吡咯烷和哌啶的途径

  摘要：

  链烯基亚氨基亚胺和链烯基亚氨基酰胺与苯硒基溴化物，碘和溴进行亲电诱导的环化反应，生成环和螺环亚胺，吡咯烷和哌啶，并在氮原子上自发裂解保护基，收率好至极佳。

  DOI：

  10.1016/j.tetlet.2005.04.060
• 作为产物：
  描述：

  2,2-二甲基-4-戊烯醛 在 titanium(IV) tetraethanolate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 4,4-dimethyl-2-phenylselanylmethyl-3,4-dihydro-2H-pyrrole
  参考文献：
  名称：

  亲电试剂诱导的烯基亚磺胺和烯基亚磺酰胺的环化反应和伴随的N-脱保护，作为直接通往环状或螺环亚胺，吡咯烷和哌啶的途径

  摘要：

  链烯基亚氨基亚胺和链烯基亚氨基酰胺与苯硒基溴化物，碘和溴进行亲电诱导的环化反应，生成环和螺环亚胺，吡咯烷和哌啶，并在氮原子上自发裂解保护基，收率好至极佳。

  DOI：

  10.1016/j.tetlet.2005.04.060

文献信息

• A New Method for the Generation and Cyclization of Iminyl Radicals via the Hudson Reaction
  作者：Xichen Lin、Didier Stien、Steven M. Weinreb

  DOI：10.1021/ol990720e

  日期：1999.8.1

  [formula: see text] A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl

  [化学式：见正文]已开发出一种温和的新合成程序，用于将亚氨基自由基原位生成和环化到侧链烯烃上，然后通过多种捕集试剂之一将所得碳自由基官能化。该方法的关键过程涉及在-50℃至室温下通过用容易获得的2，6-二甲基苯亚磺酰氯处理醛肟或酮肟来生产亚胺基（Hudson反应）。
• Development of efficient new methodology for generation, cyclization and functional trapping of iminyl and amidyl radicals
  作者：Xichen Lin、Gerald D. Artman、Didier Stien、Steven M. Weinreb

  DOI：10.1016/s0040-4020(01)00878-x

  日期：2001.10

  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.
• A sequence of electrophile induced cyclisation and concomitant N-deprotection of alkenylsulfinimines and alkenylsulfinamides as a direct route to cyclic or spirocyclic imines, pyrrolidines and piperidines
  作者：H. Ali Dondas、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2005.04.060

  日期：2005.6

  Alkenylsulfinimines and alkenylsulfinamides underwent electrophile induced cyclisation reactions with phenylselenyl bromide, iodine and bromine to cyclic and spirocyclic imines, pyrrolidines and piperidines with spontaneous cleavage of the protective group at nitrogen in good to excellent yield.

  链烯基亚氨基亚胺和链烯基亚氨基酰胺与苯硒基溴化物，碘和溴进行亲电诱导的环化反应，生成环和螺环亚胺，吡咯烷和哌啶，并在氮原子上自发裂解保护基，收率好至极佳。