c-5-(Benzyloxy)-t-2-(N,N-diethylamino)-r-1-cyclohexanol | 136667-65-7

• 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: c-5-(Benzyloxy)-t-2-(N,N-diethylamino)-r-1-cyclohexanol
• 英文别名: (1S,2S,5S)-2-(diethylamino)-5-phenylmethoxycyclohexan-1-ol
• CAS: 136667-65-7
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: PSPSFVHWNMZJOS-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1SR,3RS,6RS)-3-(benzyloxy)-7-oxabicyclo[4.1.0]heptane 在 氢氧化钾 、 sodium azide 、 lithium perchlorate 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 8.0h， 生成 c-5-(Benzyloxy)-t-2-(N,N-diethylamino)-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

• Lanthanide(III) trifluoromethanesulfonates as extraordinarily effective new catalysts for the aminolysis of 1,2-epoxides
  作者：Marco Chini、Paolo Crotti、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/0040-4039(94)85073-9

  日期：1994.1

  Lanthanide(III) trifluoromethanesulfonates (triflates), such as Yb(OTf)3, Nd(OTf)3 and Gd(OTf)3, catalyze in a extraordinarily efficient way the aminolysis of 1,2-epoxides, affording the corresponding β-amino alcohols, at room temperature and in a non-protic solvent (CH2Cl2 or toluene), in very good yields. The reactions are completely anti stereoselective and highly regioselective.

  三氟甲烷磺酸镧系元素（III），例如Yb（OTf）3，Nd（OTf）3和Gd（OTf）3以非常有效的方式催化1,2-环氧化物的氨解反应，从而提供相应的β-氨基在室温下和在非质子溶剂（CH 2 Cl 2或甲苯）中以非常高的收率得到醇。反应完全是抗立体选择性的和高度区域选择性的。