cis-1-(3-hydroxypropyl)-2-phenylcyclohexanol | 134210-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1-(3-hydroxypropyl)-2-phenylcyclohexanol
• 英文别名: (1S,2R)-1-(3-hydroxypropyl)-2-phenylcyclohexan-1-ol
• CAS: 134210-04-1；134210-06-3
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: GXIZSEVMWHKCPA-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1-(3-hydroxypropyl)-2-phenylcyclohexanol 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以71%的产率得到
  参考文献：
  名称：

  Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions

  摘要：

  The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a dominant preference for retention when R = OCH3 to modestly favored inversion when R = CH3. Experiments with O-18-labeled diols show that in the methoxyl series most of the isotope is retained irrespective of relative stereochemistry. On the other hand, the pair of phenyl-substituted isomers responds by losing approximately 50% of the label. The isotopic level in the product erodes further when R = CH3. The stereochemical and isotopic labeling results are interpreted in terms of competing intramolecular S(N)2 and classical S(N)1 pathways. The extent to which cooperative nucleophilic attack with loss of the primary hydroxyl is facilitated reaches a maximum in the methoxyl-substituted diols, as a consequence of electrostatic inhibition of tertiary carbocation formation. As this effect is progressively lessened, the percentage of S(N)1 response rises. At no time, however, do the stereoisomeric carbocations interconvert conformationally prior to cyclization.

  DOI：

  10.1021/ja00049a014
• 作为产物：
  描述：

  2-苯基环己酮 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 cis-1-(3-hydroxypropyl)-2-phenylcyclohexanol
  参考文献：
  名称：

  Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions

  摘要：

  The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a dominant preference for retention when R = OCH3 to modestly favored inversion when R = CH3. Experiments with O-18-labeled diols show that in the methoxyl series most of the isotope is retained irrespective of relative stereochemistry. On the other hand, the pair of phenyl-substituted isomers responds by losing approximately 50% of the label. The isotopic level in the product erodes further when R = CH3. The stereochemical and isotopic labeling results are interpreted in terms of competing intramolecular S(N)2 and classical S(N)1 pathways. The extent to which cooperative nucleophilic attack with loss of the primary hydroxyl is facilitated reaches a maximum in the methoxyl-substituted diols, as a consequence of electrostatic inhibition of tertiary carbocation formation. As this effect is progressively lessened, the percentage of S(N)1 response rises. At no time, however, do the stereoisomeric carbocations interconvert conformationally prior to cyclization.

  DOI：

  10.1021/ja00049a014