5-Bromo-2-phenylmethoxyoxane | 157022-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 5-Bromo-2-phenylmethoxyoxane
• CAS: 157022-99-6
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: LTPUQVTXXHDLLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-phenylmethoxyoxane 在 potassium tert-butylate 、 lithium perchlorate 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N-溴代乙酰胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 t-2-(Benzyloxy)-t-4-chlorotetrahydropyran-r-5-ol
  参考文献：
  名称：

  Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. 7. Synthesis and Ring-Opening Reactions of cis- and trans-Oxides Derived from 2-(Benzyloxy)-3,6-dihydro-2H-pyran

  摘要：

  The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalities through chelation processes assisted by metal ions was verified in a conformationally semirigid cyclic oxirane system in which the polar functionality is both directly inserted into the cyclic system and present on the cyclic system itself. Diastereoisomeric cis 4 and trans epoxide 5, derived from 2-(benzyloxy)-3,6-dihydro-2H-pyran, were prepared and some of their opening reactions (azidolysis, aminolysis, Cl- addition, and LiAlH4 reduction) were studied. The regioselectivity observed is largely dependent for both 4 and 5 on the opening (standard or metal-assisted) reaction conditions, and a regioalternating process is almost obtained.

  DOI：

  10.1021/jo00094a025
• 作为产物：
  描述：

  乙烯氧基甲基-苯 在 溴 、 二异丁基氢化铝 、 对苯二酚 作用下， 反应 18.5h， 生成 5-Bromo-2-phenylmethoxyoxane
  参考文献：
  名称：

  Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. 7. Synthesis and Ring-Opening Reactions of cis- and trans-Oxides Derived from 2-(Benzyloxy)-3,6-dihydro-2H-pyran

  摘要：

  The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalities through chelation processes assisted by metal ions was verified in a conformationally semirigid cyclic oxirane system in which the polar functionality is both directly inserted into the cyclic system and present on the cyclic system itself. Diastereoisomeric cis 4 and trans epoxide 5, derived from 2-(benzyloxy)-3,6-dihydro-2H-pyran, were prepared and some of their opening reactions (azidolysis, aminolysis, Cl- addition, and LiAlH4 reduction) were studied. The regioselectivity observed is largely dependent for both 4 and 5 on the opening (standard or metal-assisted) reaction conditions, and a regioalternating process is almost obtained.

  DOI：

  10.1021/jo00094a025

文献信息

• Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. 7. Synthesis and Ring-Opening Reactions of cis- and trans-Oxides Derived from 2-(Benzyloxy)-3,6-dihydro-2H-pyran
  作者：Marco Chini、Paolo Crotti、Cristina Gardelli、Franco Macchia

  DOI：10.1021/jo00094a025

  日期：1994.7

  The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalities through chelation processes assisted by metal ions was verified in a conformationally semirigid cyclic oxirane system in which the polar functionality is both directly inserted into the cyclic system and present on the cyclic system itself. Diastereoisomeric cis 4 and trans epoxide 5, derived from 2-(benzyloxy)-3,6-dihydro-2H-pyran, were prepared and some of their opening reactions (azidolysis, aminolysis, Cl- addition, and LiAlH4 reduction) were studied. The regioselectivity observed is largely dependent for both 4 and 5 on the opening (standard or metal-assisted) reaction conditions, and a regioalternating process is almost obtained.