4-(Benzyloxy)-1-butenyl phenyl sulfone | 162283-98-9

• 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-(Benzyloxy)-1-butenyl phenyl sulfone
• 英文别名: [(E)-4-(benzenesulfonyl)but-3-enoxy]methylbenzene
• CAS: 162283-98-9
• 化学式: C₁₇H₁₈O₃S
• 分子量: 302.394
• InChiKey: BOFCDGLFXDEEAP-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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,6R,7S)-1,4,10,10-tetramethyl-5-oxido-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-4-ene 、 4-(Benzyloxy)-1-butenyl phenyl sulfone 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 <2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-2-<2-(benzyloxy)ethyl>-3a,5,10,10-tetramethyl-5,8-methano-2H-isoxazolo<3,2-b>benzoxazol-3-yl phenyl sulfone
  参考文献：
  名称：

  [2 + 3] Cycloadditions of Enantiomerically Pure Oxazoline N-Oxides: An Alternative to the Asymmetric Aldol Condensation

  摘要：

  A series of camphor-derived oxazoline N-oxides were obtained by condensation of the appropriate orthoesters with (+)-3-(hydroxyamino)borneol (8). These unstable dipoles were used without isolation in various [2 + 3] asymmetric cyclocondensations. The regio- and diastereoselectivities of these reactions were good to excellent. After functional group transformations, adducts were cleaved by a two--step sequence (i.e., oxidation followed by acidic hydrolysis) giving beta-hydroxy ketones and (+)-3-(hydroxyimino)borneol (19). Asymmetric synthesis of (+)-1,7-dioxaspiro[5.5]-undecan-4-ol, a pheromone of Dacus oleae, was achieved as an application of this new method.

  DOI：

  10.1021/jo00111a033
• 作为产物：
  描述：

  4-溴丁醚苄酯 在 正丁基锂 、 copper diacetate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-(Benzyloxy)-1-butenyl phenyl sulfone
  参考文献：
  名称：

  [2 + 3] Cycloadditions of Enantiomerically Pure Oxazoline N-Oxides: An Alternative to the Asymmetric Aldol Condensation

  摘要：

  A series of camphor-derived oxazoline N-oxides were obtained by condensation of the appropriate orthoesters with (+)-3-(hydroxyamino)borneol (8). These unstable dipoles were used without isolation in various [2 + 3] asymmetric cyclocondensations. The regio- and diastereoselectivities of these reactions were good to excellent. After functional group transformations, adducts were cleaved by a two--step sequence (i.e., oxidation followed by acidic hydrolysis) giving beta-hydroxy ketones and (+)-3-(hydroxyimino)borneol (19). Asymmetric synthesis of (+)-1,7-dioxaspiro[5.5]-undecan-4-ol, a pheromone of Dacus oleae, was achieved as an application of this new method.

  DOI：

  10.1021/jo00111a033

文献信息

• [2 + 3] Cycloadditions of Enantiomerically Pure Oxazoline N-Oxides: An Alternative to the Asymmetric Aldol Condensation
  作者：Thierry Berranger、Yves Langlois

  DOI：10.1021/jo00111a033

  日期：1995.3

  A series of camphor-derived oxazoline N-oxides were obtained by condensation of the appropriate orthoesters with (+)-3-(hydroxyamino)borneol (8). These unstable dipoles were used without isolation in various [2 + 3] asymmetric cyclocondensations. The regio- and diastereoselectivities of these reactions were good to excellent. After functional group transformations, adducts were cleaved by a two--step sequence (i.e., oxidation followed by acidic hydrolysis) giving beta-hydroxy ketones and (+)-3-(hydroxyimino)borneol (19). Asymmetric synthesis of (+)-1,7-dioxaspiro[5.5]-undecan-4-ol, a pheromone of Dacus oleae, was achieved as an application of this new method.