t-2-Azido-c-4-(benzyloxy)-r-1-cyclohexanol | 136667-72-6

• 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-4-(benzyloxy)-r-1-cyclohexanol
• 英文别名: (1R,2R,4S)-2-azido-4-phenylmethoxycyclohexan-1-ol
• CAS: 136667-72-6
• 化学式: C₁₃H₁₇N₃O₂
• 分子量: 247.297
• InChiKey: KIJAGJGSKUZNHE-YNEHKIRRSA-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-4-(benzyloxy)-r-1-cyclohexanol 在 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以68%的产率得到t-2-Amino-c-4-(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
• 作为产物：
  描述：

  (1SR,3RS,6RS)-3-(benzyloxy)-7-oxabicyclo[4.1.0]heptane 在 sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以69%的产率得到t-2-Azido-c-4-(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

• Discovery of trisubstituted cyclohexanes as potent CC chemokine receptor 2 (CCR2) antagonists
  作者：Robert J. Cherney、John B. Brogan、Ruowei Mo、Yvonne C. Lo、Gengjie Yang、Persymphonie B. Miller、Peggy A. Scherle、Bruce F. Molino、Percy H. Carter、Carl P. Decicco

  DOI：10.1016/j.bmcl.2008.12.062

  日期：2009.2

  A series of trisubstituted cyclohexanes was designed, synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the identification of two distinct substitution patterns about the cyclohexane ring as potent and selective CCR2 antagonists. Compound 36 exhibited excellent binding (CCR2 IC50 = 2.4 nM) and functional antagonism (calcium flux IC50 = 2.0 nM and chemotaxis IC50 = 5

  设计，合成和评估了一系列三取代的环己烷作为CC趋化因子受体2（CCR2）拮抗剂。这导致鉴定出关于环己烷环的两种不同的取代模式，它们是有效的和选择性的CCR2拮抗剂。化合物36表现出优异的结合（CCR2 IC 50  = 2.4 nM）和功能拮抗作用（钙通量IC 50  = 2.0 nM，趋化性IC 50  = 5.1 nM）。