cis-1-(benzyloxy)-3,4-epoxyhexane | 121441-15-4

• 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: cis-1-(benzyloxy)-3,4-epoxyhexane
• 英文别名: (3RS,4SR)-1-(benzyloxy)-3,4-epoxyhexane；(2R,3S)-2-ethyl-3-(2-phenylmethoxyethyl)oxirane
• CAS: 121441-15-4；121441-19-8；138624-28-9；140654-16-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: LSDDBKMLZOYHFH-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1-(benzyloxy)-3,4-epoxyhexane 在 偶氮二异丁腈 、 三正丁基氢锡 、 magnesium iodide 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 1-(benzyloxy)hexan-3-ol
  参考文献：
  名称：

  Diols obtained via chemo and regioselective ring opening of epoxy alcohols: a straightforward synthesis of 2S,3S-Octandiol

  摘要：

  Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric synthesis of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.

  DOI：

  10.1016/s0040-4020(01)92240-9
• 作为产物：
  描述：

  {[(3E)-3-己烯-1-基氧基]甲基}苯 在 双氧水 、 氰基甲酸乙酯 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到cis-1-(benzyloxy)-3,4-epoxyhexane
  参考文献：
  名称：

  Ethyl Cyanoformate/Hydrogen Peroxide and Related Combination Systems, Novel Epoxidizing Systems of Olefins

  摘要：

  发现乙基氰基甲酸酯和过氧化氢的组合系统能够在室温下以立体特异性的方式对烯烃进行环氧化。使用薄荷基氰基甲酸酯/过氧化氢系统时观察到了不对称环氧化。

  DOI：

  10.1246/cl.1991.1937

文献信息

• Ethyl Cyanoformate/Hydrogen Peroxide and Related Combination Systems, Novel Epoxidizing Systems of Olefins
  作者：Yukio Masaki、Tsuyoshi Miura、Isao Mukai、Akichika Itoh、Hirohisa Oda

  DOI：10.1246/cl.1991.1937

  日期：1991.11

  A combination system of ethyl cyanoformate and hydrogen peroxide was found to epoxidize olefins in a stereospecific manner at room temperature. Asymmetric epoxidation was observed with menthyl cyanoformate/hydrogen peroxide system.

  发现乙基氰基甲酸酯和过氧化氢的组合系统能够在室温下以立体特异性的方式对烯烃进行环氧化。使用薄荷基氰基甲酸酯/过氧化氢系统时观察到了不对称环氧化。
• Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 18: Regioselectivity of the opening reactions with MeOH of 1-(benzyloxy)-2,3- and -3,4-epoxyalkanes under condensed and gas phase operating conditions
  作者：Paolo Crotti、Gabriele Renzi、Graziella Roselli、Valeria Di Bussolo、Laura Lucarelli、Maria Rosaria Romano

  DOI：10.1016/j.tet.2005.05.040

  日期：2005.8

  The regiochemical behavior of a series of aliphatic open chain epoxides bearing a heterofunctionality in an allylic or homoallylic relationship has been examined in the opening reaction with MeOH under both condensed and gas phase operating conditions. The results indicate that the proton (actually D+) possesses in the gas phase intrinsic chelating properties which are even superior than those of Li (+) in the condensed phase. (c) 2005 Elsevier Ltd. All rights reserved.
• Substituent-directed alkyl addition reactions of epoxides. 1. Applications to the synthesis of 3-hydroxy-4-methylalkanoic acids
  作者：Lee A. Flippin、Peter A. Brown、Keyvan Jalali-Araghi

  DOI：10.1021/jo00276a018

  日期：1989.7
• Diols obtained via chemo and regioselective ring opening of epoxy alcohols: a straightforward synthesis of 2S,3S-Octandiol
  作者：Carlo Bonini、Giuliana Righi

  DOI：10.1016/s0040-4020(01)92240-9

  日期：1992.2

  Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric synthesis of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.
• Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems
  作者：Francesca Azzena、Federico Calvani、Paolo Crotti、Cristina Gardelli、Franco Macchia、Mauro Pineschi

  DOI：10.1016/0040-4020(95)00633-j

  日期：1995.9

  The regiochemical outcome of the ring opening of 1:2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the

  通过单官能和双官能的脂族环氧乙烷体系在与环氧乙烷环呈均烯丙基和/或烯丙基关系的杂官能度（OR）中验证了通过金属离子辅助的螯合过程使1：2-环氧化物开环的区域化学结果。检查了OR官能团与环氧乙烷环的距离以及保护基类型对这些系统的区域化学结果的影响。在某些情况下，使用LiClO 4或Mg（ClO 4）2作为促进金属盐使得有可能获得良好的区域交替方法。