(+)-(S)-4-hydroxy-β-damascone | 1447716-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(S)-4-hydroxy-β-damascone
• 英文别名: (S)-(+)-4-hydroxy-β-damascone；(E)-1-[(3S)-3-hydroxy-2,6,6-trimethylcyclohexen-1-yl]but-2-en-1-one
• CAS: 1447716-75-7
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: NOORESDHJXLGAO-PORFMDCZSA-N

物化性质

• 沸点：
  321.4±42.0 °C(predicted)
• 密度：
  0.996±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-1-(2,6,6-三甲基-1-环己烯-1-基)-2-丁烯-1-酮 在 culture of Mortierella isabellina AM₂₁₂ 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 以54%的产率得到
  参考文献：
  名称：

  Transformation of β-damascone to (+)-(S)-4-hydroxy-β-damascone by fungal strains and its evaluation as a potential insecticide against aphids Myzus persicae and lesser mealworm Alphitobius diaperinus Panzer

  摘要：

  Microbial conversion of beta-damascone (1) into 4-hydroxy-beta-damascone (2) was studied. The results showed the potential of the tested biocatalysts for the regio- and enantioselective hydroxylation of substrate 1. The highest enantioselectivity was exhibited by strain Mortierella isabellina AM212. beta-Damascone (1) was a relatively good deterrent towards Alphitobius diaperinus and it was behaviorally inactive to Myzus persicae. The racemic compound 2 and its (+)-(S)-enantiomer were stronger antifeedants against A. diaperinus than beta-damascone (1), in the case of M persicae only (+)-(S)-(2) exhibited the deterrent properties. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2016.03.018

文献信息

• Facile lipase catalysed syntheses of (S)-(+)-4-hydroxy-β-ionone and (S)-(+)-4-hydroxy-β-damascone: chiral flavorants and synthons
  作者：Gauri P. More、Sujata V. Bhat

  DOI：10.1016/j.tetlet.2013.05.089

  日期：2013.8

  Enantioselective syntheses of (S)-(+)-4-hydroxy-β-ionone and (S)-(+)-4-hydroxy-β-damascone have been achieved through pig pancreatic lipase catalysed trans-esterification. These molecules find utility as constituent in fruit-type fragrance and flavor formulations and as chiral synthons in asymmetric synthesis of bioactive terpenoids.

  （对映选择性合成小号（+） - - 4-羟基β紫罗兰酮和（）小号） - （+） - 4-羟基β大马酮已通过猪胰脂肪酶催化的实现反-esterification。这些分子在水果型香料和香精配方中用作成分，并在生物活性萜类化合物的不对称合成中用作手性合成子。
• Transformation of β-damascone to (+)-(S)-4-hydroxy-β-damascone by fungal strains and its evaluation as a potential insecticide against aphids Myzus persicae and lesser mealworm Alphitobius diaperinus Panzer
  作者：Anna Gliszczyńska、Witold Gładkowski、Katarzyna Dancewicz、Beata Gabryś、Maryla Szczepanik

  DOI：10.1016/j.catcom.2016.03.018

  日期：2016.5

  Microbial conversion of beta-damascone (1) into 4-hydroxy-beta-damascone (2) was studied. The results showed the potential of the tested biocatalysts for the regio- and enantioselective hydroxylation of substrate 1. The highest enantioselectivity was exhibited by strain Mortierella isabellina AM212. beta-Damascone (1) was a relatively good deterrent towards Alphitobius diaperinus and it was behaviorally inactive to Myzus persicae. The racemic compound 2 and its (+)-(S)-enantiomer were stronger antifeedants against A. diaperinus than beta-damascone (1), in the case of M persicae only (+)-(S)-(2) exhibited the deterrent properties. (C) 2016 Elsevier B.V. All rights reserved.