t-2-Azido-c-5-(benzyloxy)-r-1-cyclohexanol | 136667-73-7

• 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-c-5-(benzyloxy)-r-1-cyclohexanol
• 英文别名: (+/-)-(1RS,2RS,5RS)-2-azido-5-(benzyloxy)cyclohexan-1-ol；(1R,2R,5R)-2-azido-5-phenylmethoxycyclohexan-1-ol
• CAS: 136667-73-7
• 化学式: C₁₃H₁₇N₃O₂
• 分子量: 247.297
• InChiKey: AHYYYVQVCIUXSN-JHJVBQTASA-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-c-5-(benzyloxy)-r-1-cyclohexanol 在 palladium on activated charcoal 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 氨 、 甲酸铵 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 37.91h， 生成 N6-benzoyl-9-{2'-[(tert-butyl)dimethylsilyloxy]-4'-[(4-methoxyphenyl)diphenylmethoxy]cyclohexyl}adenine
  参考文献：
  名称：

  含2，4-二羟基环己基核苷的寡核苷酸的合成与性能

  摘要：

  具有腺嘌呤和尿嘧啶碱基的环己基核苷已由2-叠氮基环己烷-1,5-二醇合成。使用（R）-O-甲基扁桃酸拆分获得的外消旋核苷。使用磷酰胺酰胺化学合成短的寡核苷酸。然而，这些寡核苷酸不显示自身杂交，并且双链体不如核吡喃糖基-（4'2'）-寡核苷酸的双链体稳定。

  DOI：

  10.1002/hlca.200590258
• 作为产物：
  描述：

  (1RS,3RS,6SR)-3-(benzyloxy)-7-oxabicyclo[4.1.0]heptane 在 sodium azide 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 t-2-Azido-c-5-(benzyloxy)-r-1-cyclohexanol 、
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00113a035

文献信息

• 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
  作者：Marco Chini、Paolo Crotti、Lee A. Flippin、Franco Macchia

  DOI：10.1021/jo00025a018

  日期：1991.12

  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.