4-[(1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl]butan-2-one | 178391-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl]butan-2-one
• CAS: 178391-41-8
• 化学式: C₁₁H₁₆Br₂O
• 分子量: 324.055
• InChiKey: BRNVDIOYDQTDHJ-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-[(1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl]butan-2-one 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正戊烷 、 苯 为溶剂， 反应 6.0h， 生成 (1R,3R)-cis-1-ethynyl-2,2-dimethyl-3-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopropane
  参考文献：
  名称：

  Detection, synthesis and absolute configuration of (+)-nortaylorione, a new terpene from Artemisia annua

  摘要：

  Nortaylorione a new nor-sesquiterpene, was identified among minor components of Artemisia annua (hybrid plants) essential oil. Its relative and absolute configurations were determined by GC and GC/MS equipped with a chiral column and coinjecting the essential oil with synthetic standards (racemic and homochiral), obtained in a few steps from commercial reagents. Pauson-Khand reaction was used as the key reaction in both synthetic pathways. The new natural product, named (+)-nortaylorione, is the (1'S)-cis-2-[2',2'-dimethyI-3'-(3 ''-butanon-l ''-yl)-cyclopropyl]2-cyclopenten-1-one. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00169-9
• 作为产物：
  描述：

  (1S,3R)-cis-2,2-dimethyl-3-(3-oxobutyl)cyclopropanecarboxylic acid 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 7.5h， 生成 4-[(1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl]butan-2-one
  参考文献：
  名称：

  乙烯修饰的Pauson-Khand反应的开发及在（+）-taylorione的全合成中的利用

  摘要：

  描述了与气态烯烃乙烯一起使用的两种互补的Pauson-Khand环合方案。这些N-氧化物促进的反应（10个实施例）显示在温和的高压釜条件下或更方便地在大气压下进行。所开发的方法已被用作倍半萜（+）-taylorione的全合成中的关键转化，这已经可以从容易获得的（+）-2-carene中以良好的总收率实现。

  DOI：

  10.1016/0040-4020(96)00259-1

文献信息

• Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione
  作者：Johannes G. Donkervoort、Alison R. Gordon、Craig Johnstone、William J. Kerr、Udo Lange

  DOI：10.1016/0040-4020(96)00259-1

  日期：1996.5

  Two complementary Pauson-Khand annulation protocols for use with the gaseous alkene, ethylene, are described. These N-oxide promoted reactions (10 examples) are shown to proceed under both mild autoclave conditions or, more conveniently, at atmospheric pressure. The developed methodology has been utilised as the key transformation in the total synthesis of the sesquiterpene (+)-taylorione which has

  描述了与气态烯烃乙烯一起使用的两种互补的Pauson-Khand环合方案。这些N-氧化物促进的反应（10个实施例）显示在温和的高压釜条件下或更方便地在大气压下进行。所开发的方法已被用作倍半萜（+）-taylorione的全合成中的关键转化，这已经可以从容易获得的（+）-2-carene中以良好的总收率实现。
• Detection, synthesis and absolute configuration of (+)-nortaylorione, a new terpene from Artemisia annua
  作者：C.M de Oliveira、V.L Ferracini、M.A Foglio、A de Meijere、A.J Marsaioli

  DOI：10.1016/s0957-4166(97)00169-9

  日期：1997.6

  Nortaylorione a new nor-sesquiterpene, was identified among minor components of Artemisia annua (hybrid plants) essential oil. Its relative and absolute configurations were determined by GC and GC/MS equipped with a chiral column and coinjecting the essential oil with synthetic standards (racemic and homochiral), obtained in a few steps from commercial reagents. Pauson-Khand reaction was used as the key reaction in both synthetic pathways. The new natural product, named (+)-nortaylorione, is the (1'S)-cis-2-[2',2'-dimethyI-3'-(3 ''-butanon-l ''-yl)-cyclopropyl]2-cyclopenten-1-one. (C) 1997 Elsevier Science Ltd.