<2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-5,10,10-trimethyl-2,3a-dipropyl-3-(hydroxymethyl)-5,8-methano-2H-isoxazolo<3,2-b>benzoxazole | 162284-06-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: <2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-5,10,10-trimethyl-2,3a-dipropyl-3-(hydroxymethyl)-5,8-methano-2H-isoxazolo<3,2-b>benzoxazole
• 英文别名: (2S-(2α,3β,3aα,4aβ,5α,8α,8aβ))-Octahydro-5,10,10-trimethyl-2,3a-dipropyl-3-(hydroxymethyl)-5,8-methano-2H-isoxazolo[3,2-b]benzoxazole；[(1S,2R,5S,6S,7S,9S,10R)-10,13,13-trimethyl-5,7-dipropyl-4,8-dioxa-3-azatetracyclo[8.2.1.02,9.03,7]tridecan-6-yl]methanol
• CAS: 162284-06-2
• 化学式: C₂₀H₃₅NO₃
• 分子量: 337.503
• InChiKey: JCBIKEOUNZQZDU-AYGHAXAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-5,10,10-trimethyl-2,3a-dipropyl-3-(hydroxymethyl)-5,8-methano-2H-isoxazolo<3,2-b>benzoxazole 在 吡啶 、 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (2S,3S)-2-[(1R,2S,4S,7S)-1,10,10-trimethyl-5-oxido-4-propyl-3-oxa-5-azoniatricyclo[5.2.1.02,6]dec-5-en-4-yl]hexan-3-ol
  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：

  tert-butyl (2E)-hex-2-enoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 <2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-5,10,10-trimethyl-2,3a-dipropyl-3-(hydroxymethyl)-5,8-methano-2H-isoxazolo<3,2-b>benzoxazole
  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.