2-(Benzyloxy)-3,6-dihydro-2H-pyran | 157023-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(Benzyloxy)-3,6-dihydro-2H-pyran
• 英文别名: 2-phenylmethoxy-3,6-dihydro-2H-pyran
• CAS: 157023-00-2
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: YGLUNANVKICXPX-UHFFFAOYSA-N

物化性质

• 沸点：
  284.2±40.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-(Benzyloxy)-3,6-dihydro-2H-pyran 在 lithium aluminium tetrahydride 、 12-冠醚-4 、 potassium tert-butylate 、 N-溴代乙酰胺 作用下， 以 正戊烷 为溶剂， 反应 10.0h， 生成 cis-2-(Benzyloxy)tetrahydropyran-4-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：

  2-(Benzyloxy)-3,4-dihydro-2H-pyran 在 溴 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-(Benzyloxy)-3,6-dihydro-2H-pyran
  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. Part 15: Regioselectivity of the opening reactions with MeOH of remote O-substituted regio- and diastereoisomeric pyranosidic epoxides under condensed- and gas-phase operating conditions
  作者：Paolo Crotti、Gabriele Renzi、Lucilla Favero、Graziella Roselli、Valeria Di Bussolo、Micaela Caselli

  DOI：10.1016/s0040-4020(03)00078-4

  日期：2003.2

  The regiochemical behavior of pairs of regio- and diastereoisomeric epoxides derived from the 3,4,5,6-tetrahydro-2H-pyrane system, bearing an acetal group as the remote functionality, was determined in the acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D3+), as the promoting agent. With only one exception, the results obtained

  在缩合相的酸性甲醇分解中，确定了由3,4,5,6-四氢-2 H-吡喃体系衍生的成对的对-对映体和非对映异构体环氧化物的对区域化学行为（以缩醛为远程官能团）（ cd-相）和在气相中与MeOH的反应中，使用气态酸（D 3 +）作为促进剂。仅有一个例外，在这些环氧化物的打开过程中获得的结果表明，D +介导的螯合双齿物种在气相中的侵入能够改变在cd相甲醇解中发现的区域化学结果。
• Regiochemical control of the ring opening of aziridines by means of chelating processes. 2. Synthesis and ring-opening reactions of aziridines derived from 5,6-dihydro-2H-pyran and of the diastereoisomeric cis- and trans-aziridines derived from 3-(benzyloxy)cyclohexene, 2-(benzyloxy)-3,6-dihydro-, and 2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Mauro Pineschi

  DOI：10.1016/s0040-4020(96)01054-x

  日期：1997.1

  The regiochemical outcome of the ring opening of the activated and unactivated title aziridines was examined. In some cases a nice degree of regiocontrol can be obtained depending on the opening reaction conditions (standard, metal-assisted, or under acid-proton catalysis). The results have been rationalized by admitting the incursion, under appropriate reaction conditions, of chelated bidentate structures

  检查了活化的和未活化的标题氮丙啶的开环的区域化学结果。在某些情况下，取决于打开的反应条件（标准，金属辅助或在酸-质子催化下），可以获得很好的区域控制程度。通过允许在适当的反应条件下侵入金属或某些情况下质子在氮丙啶氮与O-杂官能团之间配位的螯合二齿结构，使结果合理化。
• 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.