(1E,3S)-1-phenylpent-1-en-4-yn-3-ol | 14604-31-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (1E,3S)-1-phenylpent-1-en-4-yn-3-ol
• 英文别名: (R)-(+)-1-phenyl-1-penten-4-yn-3-ol；(E,3S)-1-phenylpent-1-en-4-yn-3-ol
• CAS: 14604-31-0；31450-17-6；129571-74-0；129646-83-9
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: FZGJGBSLOXLHAL-ANYFNZRUSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  130-140 °C(Press: 12 Torr)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (1E,3S)-1-phenylpent-1-en-4-yn-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-1-phenylpentan-3-ol
  参考文献：
  名称：

  Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp

  摘要：

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.

  DOI：

  10.1021/ja00016a032
• 作为产物：
  描述：

  (E)-1-phenylpent-1-en-4-yn-3-ol 以28%的产率得到(1E,3S)-1-phenylpent-1-en-4-yn-3-ol
  参考文献：
  名称：

  Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp

  摘要：

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.

  DOI：

  10.1021/ja00016a032

文献信息

• Kinetic resolutions of chiral unsaturated alcohols that cannot be resolved efficiently via enantioselective epoxidation
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00176a076

  日期：1990.9
• Facile, Asymmetric Addition of Acetylene to Aldehydes:In Situ Generation of Reactive Zinc Acetylide
  作者：Hiroshi Sasaki、Dean Boyall、Erick M. Carreira

  DOI：10.1002/1522-2675(20010418)84:4<964::aid-hlca964>3.0.co;2-i

  日期：2001.4.18

  This study documents a process in which acetylene is employed directly in nucleophilic additions to aldehydes to give adducts in high levels of enantiomeric induction, up to 98% ee. To the best of our knowledge, this represents the first time in which acetylene itself has been utilized in such ligand-controlled enantioselective additions.