(Z)-4-ethyl-4-methyl-3-[(dimethyl-phenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one | 945627-94-1

• 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: (Z)-4-ethyl-4-methyl-3-[(dimethyl-phenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one
• 英文别名: (3Z)-3-[[dimethyl(phenyl)silyl]methylidene]-4-ethyl-4-methyl-1-(4-methylphenyl)sulfonylazetidin-2-one
• CAS: 945627-94-1
• 化学式: C₂₂H₂₇NO₃SSi
• 分子量: 413.613
• InChiKey: LYOUZPDTUVCFTK-CAPFRKAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-ethyl-4-methyl-3-[(dimethyl-phenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到3-benzyl-4-ethyl-4-methyl-1-(p-tosyl)-1-azetidin-2-one
  参考文献：
  名称：

  Silylation–desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams

  摘要：

  Propargyl functionalised beta-silylalkenals were easily prepared starting from suitable propargyl compounds by a silylformylation process. In particular the use of propargyl tosyl amides allowed the synthesis of alpha, beta-unsaturated aldehydes through a two-step sequence of silylformylation -desilylation reactions. TBAF was employed to induce the desilylation process that was performed under very mild experimental conditions and occurred along with an elimination step of the tosylamido moiety affording 2-methylaryl-2-alkenals with good yields and stereoselectivity. When the tosyl amides were reacted with a hydrosilane in the presence of catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) alpha-silylmethylene-beta-lactams were synthesised through a silylcarbocyclisation process. A high chemoselectivity towards the b-lactam was observed when dialkyl propargyl amides were employed. The obtained b-lactams were easily transformed into the corresponding methylaryl-b-lactams by fluoride induced aryl migration -desilylation with total retention of configuration of the migrating group and complete stereoselectivity towards the more stable b-lactam (E)-isomer. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.04.064
• 作为产物：
  描述：

  3-甲基-3-氨基-1-戊炔 在 dodecacarbonyltetrarhodium(0) sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 50.0~100.0 ℃ 、3.04 MPa 条件下， 反应 4.0h， 生成 (Z)-4-ethyl-4-methyl-3-[(dimethyl-phenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one
  参考文献：
  名称：

  Silylation–desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams

  摘要：

  Propargyl functionalised beta-silylalkenals were easily prepared starting from suitable propargyl compounds by a silylformylation process. In particular the use of propargyl tosyl amides allowed the synthesis of alpha, beta-unsaturated aldehydes through a two-step sequence of silylformylation -desilylation reactions. TBAF was employed to induce the desilylation process that was performed under very mild experimental conditions and occurred along with an elimination step of the tosylamido moiety affording 2-methylaryl-2-alkenals with good yields and stereoselectivity. When the tosyl amides were reacted with a hydrosilane in the presence of catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) alpha-silylmethylene-beta-lactams were synthesised through a silylcarbocyclisation process. A high chemoselectivity towards the b-lactam was observed when dialkyl propargyl amides were employed. The obtained b-lactams were easily transformed into the corresponding methylaryl-b-lactams by fluoride induced aryl migration -desilylation with total retention of configuration of the migrating group and complete stereoselectivity towards the more stable b-lactam (E)-isomer. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.04.064

文献信息

• Silylation–desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams
  作者：Laura Antonella Aronica、Giulia Valentini、Anna Maria Caporusso、Piero Salvadori

  DOI：10.1016/j.tet.2007.04.064

  日期：2007.7

  Propargyl functionalised beta-silylalkenals were easily prepared starting from suitable propargyl compounds by a silylformylation process. In particular the use of propargyl tosyl amides allowed the synthesis of alpha, beta-unsaturated aldehydes through a two-step sequence of silylformylation -desilylation reactions. TBAF was employed to induce the desilylation process that was performed under very mild experimental conditions and occurred along with an elimination step of the tosylamido moiety affording 2-methylaryl-2-alkenals with good yields and stereoselectivity. When the tosyl amides were reacted with a hydrosilane in the presence of catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) alpha-silylmethylene-beta-lactams were synthesised through a silylcarbocyclisation process. A high chemoselectivity towards the b-lactam was observed when dialkyl propargyl amides were employed. The obtained b-lactams were easily transformed into the corresponding methylaryl-b-lactams by fluoride induced aryl migration -desilylation with total retention of configuration of the migrating group and complete stereoselectivity towards the more stable b-lactam (E)-isomer. (c) 2007 Published by Elsevier Ltd.