t-2-Azido-t-5-(benzyloxy)-r-1-cyclohexanol | 136667-75-9

• 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: t-2-Azido-t-5-(benzyloxy)-r-1-cyclohexanol
• 英文别名: (1S,2S,5R)-2-azido-5-phenylmethoxycyclohexan-1-ol
• CAS: 136667-75-9
• 化学式: C₁₃H₁₇N₃O₂
• 分子量: 247.297
• InChiKey: AHYYYVQVCIUXSN-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-2-Azido-t-5-(benzyloxy)-r-1-cyclohexanol 在 吡啶 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 (1β,4β,6α)-4-(Benzyloxy)-8-oxo-7-oxa-9-azabicyclo<4.3.0>nonane
  参考文献：
  名称：

  Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 3. Aminolysis and azidolysis of the cis- and trans-oxides derived from 4-(benzyloxy)cyclohexene

  摘要：

  The previously observed regiocontrol of the ring-opening of epoxides bearing a remote polar group such as the title compounds (1 and 2) can also be achieved by metal-assisted methods for the direct aminolysis and azidolysis of epoxides. The appropriate use of the metal-assisted chelating or nonchelating procedures in the ring-opening of cis-epoxide 1 effects practically complete regiocontrol of these reactions, thus leading to regioalternating processes for the aminolysis and the azidolysis of 1.

  DOI：

  10.1021/jo00025a018
• 作为产物：
  描述：

  (1RS,3RS,6SR)-3-(benzyloxy)-7-oxabicyclo[4.1.0]heptane 在 sodium azide 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以72%的产率得到t-2-Azido-t-5-(benzyloxy)-r-1-cyclohexanol
  参考文献：
  名称：

  Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 3. Aminolysis and azidolysis of the cis- and trans-oxides derived from 4-(benzyloxy)cyclohexene

  摘要：

  The previously observed regiocontrol of the ring-opening of epoxides bearing a remote polar group such as the title compounds (1 and 2) can also be achieved by metal-assisted methods for the direct aminolysis and azidolysis of epoxides. The appropriate use of the metal-assisted chelating or nonchelating procedures in the ring-opening of cis-epoxide 1 effects practically complete regiocontrol of these reactions, thus leading to regioalternating processes for the aminolysis and the azidolysis of 1.

  DOI：

  10.1021/jo00025a018

文献信息

• Regiochemical Control of the Ring Opening of Aziridines by Means of Chelating Processes. Synthesis and Ring-Opening Reactions of cis- and trans-Aziridines Derived from 4-(Benzyloxy)cyclohexene
  作者：Paolo Crotti、Lucilla Favero、Cristina Gardelli、Franco Macchia、Mauro Pineschi

  DOI：10.1021/jo00113a035

  日期：1995.4

  The regiochemical outcome of the ring opening of aziridines bearing a polar remote functionality was verified in a conformationally semirigid bicyclic system in which the polar functionality (OBn) is in an homoallylic relationship to the aziridine ring. The couples of diastereoisomeric unactivated cis-3 and trans-4 and activated aziridines cis-5 and -7 and trans-6 and -8 derived from 4-(benzyloxy)-cyclohexene were prepared, and some of their opening reactions were studied. The regioselectivity observed in the opening reactions of the cis derivatives turned out to depend largely on the opening (standard, strongly acidic, or metal-assisted) reaction conditions, thus providing a nice regioalternating process. The results obtained are rationalized by admitting the incursion of chelate bidentate intermediate structures in which the proton or the metal is actively involved.