(R)-4-hydroxy-1-penten-3-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-hydroxy-1-penten-3-one
• 英文别名: (4R)-4-hydroxypent-1-en-3-one
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: NFMJLRWCAGAETO-SCSAIBSYSA-N

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

• 作为产物：
  描述：

  3-hydroperoxypent-4-en-2-ol 在 4-二甲氨基吡啶 、 phosphate buffer 、 CAL-B lipase 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-4-hydroxy-1-penten-3-one
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of α,β-unsaturated α′-acetoxy ketones

  摘要：

  The lipase-catalyzed kinetic resolutions of the alpha,beta-unsaturated alpha'-acetoxy ketones 3a,b have been investigated. Of the lipases examined, CAL-B from Candida antarctica (fraction B) has been shown to be an efficient biocatalyst, which may be used effectively in preparative scale reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00006-8

文献信息

• 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.
• Lipase-catalyzed kinetic resolution of α,β-unsaturated α′-acetoxy ketones
  作者：Waldemar Adam、Marı́a Teresa Dı́az、Chantu R Saha-Möller

  DOI：10.1016/s0957-4166(98)00006-8

  日期：1998.3

  The lipase-catalyzed kinetic resolutions of the alpha,beta-unsaturated alpha'-acetoxy ketones 3a,b have been investigated. Of the lipases examined, CAL-B from Candida antarctica (fraction B) has been shown to be an efficient biocatalyst, which may be used effectively in preparative scale reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.