(1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane | 208516-68-1

• 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: (1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane
• 英文别名: [(1S,2S)-1-ethenyl-2-methylcyclopropyl] 4-methylbenzenesulfonate
• CAS: 208516-68-1
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: VOWBWUYCGNECCY-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane 在 sodium azide 、 15-冠醚-5 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 生成 (1S,2S)-1-Azido-2-methyl-1-vinyl-cyclopropane
  参考文献：
  名称：

  Diastereoselective palladium(0)-catalyzed azidation of 1-alkenylcyclopropyl esters: asymmetric synthesis of (−)-(1R,2S)-norcoronamic acid

  摘要：

  Palladium(0)-catalyzed azidation of (1R,2S)-1-(1-alkenyl)2-methylcyclopropyl esters 10a,b proceeds with complete retention of configuration to provide, after reduction of the azide and oxidative cleavage of the allylic double bond, the (1R,2S)-norcoronamic acid 22 (>99% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00107-4
• 作为产物：
  描述：

  对甲苯磺酰氯 、 (1S,2S)-2-Methyl-1-vinyl-cyclopropanol 以 四氢呋喃 为溶剂， 生成 (1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane
  参考文献：
  名称：

  Diastereoselective palladium(0)-catalyzed azidation of 1-alkenylcyclopropyl esters: asymmetric synthesis of (−)-(1R,2S)-norcoronamic acid

  摘要：

  Palladium(0)-catalyzed azidation of (1R,2S)-1-(1-alkenyl)2-methylcyclopropyl esters 10a,b proceeds with complete retention of configuration to provide, after reduction of the azide and oxidative cleavage of the allylic double bond, the (1R,2S)-norcoronamic acid 22 (>99% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00107-4

文献信息

• Diastereoselective cycloaddition of alkylidenecyclopropane nitrones from palladium(0)-catalyzed nucleophilic substitution of asymmetric 1-alkenylcyclopropyl esters by amino acids
  作者：Federica Pisaneschi、Franca M Cordero、Andrea Goti、Renée Paugam、Jean Ollivier、Alberto Brandi、Jacques Salaün

  DOI：10.1016/s0957-4166(00)00006-9

  日期：2000.3

  The asymmetric construction of perhydropyrrolo[3,4-b]pyridine derivatives was performed by chemo- and regioselective formation of enantiopure alkylidenecyclopropane nitrones, followed by diastereoselective intramolecular 1,3-dipolar cycloaddition. The resulting spirocyclopropane isoxazolidines then underwent thermally induced regioselective ring expansion into optically active diazaheterocycles. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective palladium(0)-catalyzed azidation of 1-alkenylcyclopropyl esters: asymmetric synthesis of (−)-(1R,2S)-norcoronamic acid
  作者：Valérie Atlan、Sandrine Racouchot、Michael Rubin、Claudia Bremer、Jean Ollivier、Armin de Meijere、Jacques Salaün

  DOI：10.1016/s0957-4166(98)00107-4

  日期：1998.4

  Palladium(0)-catalyzed azidation of (1R,2S)-1-(1-alkenyl)2-methylcyclopropyl esters 10a,b proceeds with complete retention of configuration to provide, after reduction of the azide and oxidative cleavage of the allylic double bond, the (1R,2S)-norcoronamic acid 22 (>99% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.