4-(苄氧基)丁基苯基砜 | 104948-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(苄氧基)丁基苯基砜
• 英文名称: 4-(Benzyloxy)butyl phenyl sulfone
• 英文别名: 4-(benzenesulfonyl)butoxymethylbenzene
• CAS: 104948-24-5
• 化学式: C₁₇H₂₀O₃S
• 分子量: 304.41
• InChiKey: CRYMCVMCQUHMOW-UHFFFAOYSA-N

物化性质

• 沸点：
  473.6±37.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(苄氧基)丁基苯基砜 在 正丁基锂 、 copper diacetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 <2S-(2α,3β,3aα,4aβ,5α,8α,8aβ)>-Octahydro-2-<2-(benzyloxy)ethyl>-3a-<4-(benzyloxy)butyl>-5,10,10-trimethyl-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 、 sodium benzenesulfonate 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到4-(苄氧基)丁基苯基砜
  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

• Stereocontrol in the intramolecular Diels-Alder reaction. 7. Use of the trimethylsilyl group as a removable stereocontrol element to provide greatly enhanced levels of diastereoselection
  作者：Robert K. Boeckman、Thomas E. Barta

  DOI：10.1021/jo00218a040

  日期：1985.9
• BOECKMAN, R. K. ,, JR.;BARTA, T. E., J. ORG. CHEM., 1985, 50, N 18, 3421-3423
  作者：BOECKMAN, R. K. ,, JR.、BARTA, T. E.

  DOI：——

  日期：——