6-hydroxy-8-phenyl-4-octanone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-hydroxy-8-phenyl-4-octanone
• 英文别名: 6-hydroxy-8-phenyloctan-4-one
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: PRPXUSICPWAFDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  苯丙醛 、 2-戊酮 在 polymer-C₆H₄(CH₂)5-N(iPr)Li 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 以93%的产率得到6-hydroxy-8-phenyl-4-octanone
  参考文献：
  名称：

  使用聚合物结合的锂酰胺的交叉羟醛反应

  摘要：

  聚合物结合的氨基化锂用于醛醇反应。在聚合物主链和反应位点之间引入间隔基对于提高羟醛产物的产率很重要。在转化为氨基化锂后，聚合物结合的试剂在同一反应中重复使用。

  DOI：

  10.1246/cl.2003.342

文献信息

• Crossed Aldol Reaction Using Polymer-bound Lithium Amides
  作者：Atsushi Seki、Youichi Takizawa、Fusae Ishiwata、Masatoshi Asami

  DOI：10.1246/cl.2003.342

  日期：2003.4

  Polymer-bound lithium amides were used in an aldol reaction. The introduction of a spacer between the polymer backbone and the reactive site was important to enhance yields of the aldol products. The polymer-bound reagent was repeatedly used in the same reaction after the conversion to the lithium amide.

  聚合物结合的氨基化锂用于醛醇反应。在聚合物主链和反应位点之间引入间隔基对于提高羟醛产物的产率很重要。在转化为氨基化锂后，聚合物结合的试剂在同一反应中重复使用。
• Crossed aldol reaction using cross-linked polymer-bound lithium dialkylamide
  作者：Atsushi Seki、Fusae Ishiwata、Youichi Takizawa、Masatoshi Asami

  DOI：10.1016/j.tet.2004.04.026

  日期：2004.5

  Cross-linked polymer-bound lithium dialkylamides were employed in crossed aldol reaction of various carbonyl compounds with aldehydes to afford the corresponding beta-hydroxycarbonyl compounds. The introduction of spacer chains to the polymer-bound lithium dialkylamide between the base moiety and the polystyrene backbone effectively enhanced yields of the desired aldol adducts. Sometimes better yields were obtained by using the polymer-bound reagent having an appropriate spacer-chain with those obtained using lithium diisopropylamide under homogeneous conditions. Repeated use of these polymeric reagents was demonstrated with no loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.
• Engineered Artificial Carboligases Facilitate Regioselective Preparation of Enantioenriched Aldol Adducts
  作者：Duncan S. Macdonald、Xavier Garrabou、Cindy Klaus、Rebecca Verez、Takahiro Mori、Donald Hilvert

  DOI：10.1021/jacs.0c02351

  日期：2020.6.10

  the binding and activation of specific aldol donors, as well as their subsequent reaction with diverse aldehyde acceptors. Broadening the substrate scope of this evolutionarily naïve catalyst proved much easier than previous attempts to redesign natural aldolases, suggesting that such proteins may be excellent starting points for the development of customized biocatalysts for diverse practical applications

  控制羟醛添加的区域和立体选择性通常具有挑战性。在这里，我们展示了对作为醛醇供体的丙酮具有高度特异性的人工醛缩酶可以通过单个活性位点突变重新设计，以接受具有显着效率、区域选择性和立体控制的线性和环状脂肪族酮。生化和晶体学数据显示突变的残基如何调节特定醛醇供体的结合和活化，以及它们随后与不同醛受体的反应。事实证明，扩大这种进化幼稚催化剂的底物范围比以前重新设计天然醛缩酶要容易得多，这表明此类蛋白质可能是开发用于各种实际应用的定制生物催化剂的极好起点。