4-(4-hydroxyphenyl)butan-2-one-1,1,1,3,3-d₅ | 182219-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-hydroxyphenyl)butan-2-one-1,1,1,3,3-d₅
• 英文别名: [4-(4-hydroxyphenyl)butan-2-one]-d₅；4-(4'-Hydroxyphenyl)-2-butanone-d5；1,1,1,3,3-pentadeuterio-4-(4-hydroxyphenyl)butan-2-one
• CAS: 182219-43-8
• 化学式: C₁₀H₁₂O₂
• 分子量: 169.164
• InChiKey: NJGBTKGETPDVIK-ZBJDZAJPSA-N

物化性质

• 熔点：
  >80oC (dec.)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxyphenyl)butan-2-one-1,1,1,3,3-d₅ 在 fungus Beauveria bassiana 作用下， 反应 72.0h， 生成 4-(2,2-Dideuterio-2-hydroxyethyl)phenol
  参考文献：
  名称：

  Biogeneration and Biodegradation of Raspberry Ketone in the Fungus Beauveria bassiana

  摘要：

  In growing cultures of the fungus Beauveria bassiana (ATCC 7159) the incubation of 4-(4'-hydroxyphenyl)but-3-en-2-one (p-hydroxybenzylidenacetone, 3), of 4-(4'-hydroxyphenyl)butan-2-one (raspberry ketone, 1), and of the S and R,S forms of 4-(4'-hydroxyphenyl)butan-2-ol (2) yields 2-(4'-hydroxyphenyl)ethanol (tyrosol, 4) as a final product. The experiments support the view that the actual substrate for the Baeyer-Villiger-type degradation is raspberry ketone (1) and that there is a kinetic preference in the microbial enzymatic system for the oxidation to 1 of the S form of the 4-(4'-hydroxyphenyl)butan-2-ol (2).

  DOI：

  10.1021/jf9508054
• 作为产物：
  描述：

  覆盆子酮 在 重水 、 barium(II) oxide 作用下， 以 四氢呋喃 为溶剂， 以23.3 mg的产率得到4-(4’-羟基苯基)-
  参考文献：
  名称：

  BaO 催化的酮、砜、亚砜和腈的 α-氘化

  摘要：

  在此，实现了 BaO 催化的酮、砜、亚砜和腈的 α-氘化。以高产率和高 d-掺入获得所需的氘化产物。该协议具有广泛的功能组耐受性，并且可扩展并适用于制备示例性生物活性酮候选物。

  DOI：

  10.1002/ejoc.202201218

文献信息

• An Algorithm for the Deconvolution of Mass Spectrosopic Patterns in Isotope Labeling Studies. Evaluation for the Hydrogen−Deuterium Exchange Reaction in Ketones
  作者：Christian C. Gruber、Gustav Oberdorfer、Constance V. Voss、Jennifer M. Kremsner、C. Oliver Kappe、Wolfgang Kroutil

  DOI：10.1021/jo070831o

  日期：2007.7.1

  180 °C within 40−200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75−94 h to 40−200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols

  描述和评估了一种易于使用的计算机化算法，用于根据质谱数据确定每种标记物质的数量，这些物质的掺入同位素标记物的数量不同。使用该算法，在时间、温度和标记程度方面优化了通过氢-氘交换与氧化氘交换各种 α 标记的氘酮的微波辅助合成。对于热稳定的酮，α-质子的交换是在 180 °C 下在 40-200 分钟内实现的。与回流条件相比，微波辅助方案将所需的反应时间从 75-94 小时减少到 40-200 分钟。
• One-Pot Sequential Hydrogen Isotope Exchange/Reductive Deuteration for the Preparation of α,β-Deuterated Alcohols using Deuterium Oxide
  作者：Hengzhao Li、Zemin Lai、Mengqi Peng、Lei Ning、Qixin Dong、Yuxia Hou、Jie An

  DOI：10.1021/acs.orglett.2c01940

  日期：2022.7.29

  An efficient one-pot sequential hydrogen isotope exchange (HIE)/reductive deuteration approach was developed for the preparation of α,β-deuterated alcohols using ketones as the precursors. The HIE step can also be used for the synthesis of α-deuterated ketones. This method has been applied in the synthesis of four deuterated drug and MS internal standards.

  开发了一种高效的一锅顺序氢同位素交换 (HIE)/还原氘化方法，用于以酮为前体制备 α,β-氘代醇。HIE 步骤也可用于合成 α-氘代酮。该方法已应用于四种氘代药物和质谱内标的合成。
• Stereochemistry of the Baeyer−Villiger-Type Conversion of 4-(4-Hydroxyphenyl)butan-2-one (Raspberry Ketone) into Tyrosol Mediated by <i>Beauveria bassiana</i>
  作者：Giovanni Fronza、Claudio Fuganti、Giuseppe Pedrocchi-Fantoni、Valentina Perozzo、Stefano Servi、Gioia Zucchi、Daniel Joulain

  DOI：10.1021/jo9614553

  日期：1996.1.1

  Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-H-2(2)]-4-(4-hydroxyphenyl)-butan-2-ol (15) and (2R,3R)-[1,3-H-2(4)]-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (IR)-[1-H-2]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6-C-4 framework of the intermediate raspberry ketone 1 to give the C-6-C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, prepared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.