5-(Benzyloxy)-1,1,1-trimethoxypentane | 162283-97-8

• 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: 5-(Benzyloxy)-1,1,1-trimethoxypentane
• 英文别名: Benzene, [[(5,5,5-trimethoxypentyl)oxy]methyl]-；5,5,5-trimethoxypentoxymethylbenzene
• CAS: 162283-97-8
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: UAYJYTAEDKLRKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.0±42.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(Benzyloxy)-1,1,1-trimethoxypentane 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 75.0h， 生成 (4S,6S)-(+)-4-hydroxy-1,7-dioxaspiro<5.5>undecane
  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：

  5-(benzyloxy)pentanenitrile 在 盐酸 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 96.0h， 生成 5-(Benzyloxy)-1,1,1-trimethoxypentane
  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.