(+/-)-4-hydroxy-1-penten-3-one | 22141-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-4-hydroxy-1-penten-3-one
• 英文别名: 4-Hydroxy-1-penten-3-one；4-hydroxypent-1-en-3-one
• CAS: 22141-92-0
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: NFMJLRWCAGAETO-UHFFFAOYSA-N

物化性质

• 沸点：
  165.2±23.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)
• 保留指数：
  1372

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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-hydroxy-1-penten-3-one 在 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 对甲苯磺酸 作用下， 生成 戊-4-烯-2,3-二酮
  参考文献：
  名称：

  Synthesis of vinyl 1,2-diketones

  摘要：

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.157
• 作为产物：
  描述：

  3-penten-2-ol 在 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl 、 氧气 、 tetraphenylporphyrin 、 对甲苯磺酸 作用下， 以 四氯化碳 为溶剂， 生成 (+/-)-4-hydroxy-1-penten-3-one
  参考文献：
  名称：

  Synthesis of vinyl 1,2-diketones

  摘要：

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.157

文献信息

• Chemoenzymatic Synthesis of Aroma Active 5,6-Dihydro- and Tetrahydropyrazines from Aliphatic Acyloins Produced by Baker's Yeast
  作者：Toshinari Kurniadi、Rachid Bel Rhlid、Laurent-Bernard Fay、Marcel-Alexandre Juillerat、Ralf Günter Berger

  DOI：10.1021/jf0261809

  日期：2003.5.1

  Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines

  以面包酵母的整个细胞为催化剂，通过脂肪族醛和2-酮羧酸的生物转化，产生了二十五个酰化甘油。首次合成了其中的六种酰基辅酶，并对其进行了初步鉴定。随后在温和的条件下与1,2-丙二胺发生化学反应，导致形成了十三种5,6-二氢吡嗪和六种四氢吡嗪。对它们的气味质量进行了评估，并估计了它们的气味阈值。在这些吡嗪衍生物中，2-乙基-3,5-二甲基-5,6-二氢吡嗪（烤，坚果，0.002 ng / L空气），2,3-二乙基-5-甲基-5,6-二氢吡嗪（烤，空气中的浓度为0.004 ng / L）和2-乙基-3,5-二甲基四氢吡嗪（面包类面包皮，空气中的浓度为1.9 ng / L）是气味最强烈的活性化合物。
• Hoff,S. et al., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, p. 1179 - 1184
  作者：Hoff,S. et al.

  DOI：——

  日期：——
• Hydroxy-Group Directivity in the Nitroso Ene Reaction:  Diastereo- and Regioselective Amination of Chiral Allylic Alcohols
  作者：Waldemar Adam、Nils Bottke

  DOI：10.1021/ja001752w

  日期：2000.10.1
• Enantiogenic synthesis of (R)-(−)-3-hydroxy-1-penten-4-one
  作者：Toshinari H. Kurniadi、Rachid Bel Rhlid、Marcel A. Juillerat、Martin Schüler、Ralf G. Berger

  DOI：10.1016/s0957-4166(02)00800-5

  日期：2003.2

  Condensation of pyruvate and acrolein with whole cells of baker's yeast resulted in a mixture of 3-hydroxy-1-penten-4-one 1 and 4-hydroxy-1-penten-3-one 2. The absolute configuration (R) and the enantiomeric excess (ee 72%) of the compound 1 were determined. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of vinyl 1,2-diketones
  作者：Lothar W. Habel、Sigrid De Keersmaecker、Joos Wahlen、Pierre A. Jacobs、Dirk E. De Vos

  DOI：10.1016/j.tetlet.2004.03.157

  日期：2004.5

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.