(+/-)-4,4-dimethyl-3-phenyl-1-pentanol | 61136-73-0

• 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: (+/-)-4,4-dimethyl-3-phenyl-1-pentanol
• 英文别名: 3-Phenyl-4,4-dimethyl-pentan-1-ol；4,4-Dimethyl-3-phenylpentan-1-ol
• CAS: 61136-73-0
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: ORMQZBOTAIGXCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-4,4-dimethyl-3-phenyl-1-pentanol 以22%的产率得到(S)-4,4-dimethyl-3-phenylpentan-1-ol
  参考文献：
  名称：

  Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol

  摘要：

  Enantio selective acylation of some(+/-)-3-alkyl-3-phenyl-1-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the gamma-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (+/-)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme (R) L-6/chloroform/vinyl propionate/38 degrees C and Chirazyme (R) L-7/di-iso-propyl ether/vinyl propionate/0 degrees C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (> 98%) and in 25% and 22% yield, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.002
• 作为产物：
  描述：

  肉桂酸 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+/-)-4,4-dimethyl-3-phenyl-1-pentanol
  参考文献：
  名称：

  Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol

  摘要：

  Enantio selective acylation of some(+/-)-3-alkyl-3-phenyl-1-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the gamma-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (+/-)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme (R) L-6/chloroform/vinyl propionate/38 degrees C and Chirazyme (R) L-7/di-iso-propyl ether/vinyl propionate/0 degrees C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (> 98%) and in 25% and 22% yield, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.002

文献信息

• ALVAREZ-IBARRA, C.;ARIAS, PEREZ, M. S.;GARCIA, ROMO, M. T.;PEREZ-OSSORIO,+, AN. QUIM. PUBL. REAL. SOC. ESP. FIS. Y QUIM., 1981, 77, N 1, 40-47
  作者：ALVAREZ-IBARRA, C.、ARIAS, PEREZ, M. S.、GARCIA, ROMO, M. T.、PEREZ-OSSORIO,+

  DOI：——

  日期：——
• Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol
  作者：Sunil Sabbani、Erik Hedenström、Jimmy Andersson

  DOI：10.1016/j.tetasy.2007.07.002

  日期：2007.7

  Enantio selective acylation of some(+/-)-3-alkyl-3-phenyl-1-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the gamma-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (+/-)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme (R) L-6/chloroform/vinyl propionate/38 degrees C and Chirazyme (R) L-7/di-iso-propyl ether/vinyl propionate/0 degrees C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (> 98%) and in 25% and 22% yield, respectively. (c) 2007 Elsevier Ltd. All rights reserved.