(R)-3-oxobutan-2-yl benzoate | 171194-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-oxobutan-2-yl benzoate
• 英文别名: [(2R)-3-oxobutan-2-yl] benzoate
• CAS: 171194-77-7
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: QVKRDNMNSHRBKK-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸三甲基硅酯 、 (R)-3-oxobutan-2-yl benzoate 在 三乙胺 作用下， 生成 Benzoic acid (R)-1-methyl-2-trimethylsilanyloxy-allyl ester
  参考文献：
  名称：

  1,4-Diastereoselectivity in the aldol condensation of methyl ketones

  摘要：

  DOI：

  10.1021/jo00300a008
• 作为产物：
  描述：

  (R,E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-yl benzoate 在 臭氧 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以57%的产率得到(R)-3-oxobutan-2-yl benzoate
  参考文献：
  名称：

  The enantiomers of Iralia®: preparation and odour evaluation

  摘要：

  The enantiomers of methyl ionones 1 and 2 were prepared by an enzyme-catalysed approach. Their odour properties were evaluated by skilful perfumers. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.022

文献信息

• Biocatalytic Racemization of α-Hydroxy Ketones (Acyloins) at Physiological Conditions usingLactobacillus paracasei DSM 20207
  作者：Bettina M. Nestl、Wolfgang Kroutil、Kurt Faber

  DOI：10.1002/adsc.200606055

  日期：2006.5

  Biocatalytic racemization of open-chain and cyclic dialkyl-, alkyl-aryl- and diaryl-substituted acyloins was accomplished using whole resting cells of Lactobacillus paracasei DSM 20207. The mild (physiological) reaction conditions ensured the suppression of undesired side reactions, such as elimination or condensation. This novel biocatalytic isomerization protocol represents an essential tool for

  使用副干酪乳杆菌DSM 20207的整个静息细胞完成了开链和环状的二烷基，烷基-芳基和二芳基取代的酰基辅酶的生物催化消旋作用。温和的（生理）反应条件确保了抑制不良副反应的产生，例如消除或结露。这种新颖的生物催化异构化方案代表了用于药理学重要组成部分脱硝的必不可少的工具。
• Biocatalytic racemization of synthetically important functionalized α-hydroxyketones using microbial cells
  作者：Bettina M. Nestl、Anne Bodlenner、Rainer Stuermer、Bernhard Hauer、Wolfgang Kroutil、Kurt Faber

  DOI：10.1016/j.tetasy.2007.06.005

  日期：2007.7

  Biocatalytic racemization of straight-chain and cyclic acyloins bearing (halo)alkyl, alkenyl and functionalized (hetero)aryl moieties was accomplished using whole resting cells of bacteria, fungi and yeasts. Mild physiological reaction conditions ensured the suppression of undesired side-reactions, such as elimination or condensation. This biocatalytic protocol represents a useful tool for the clean racemization of unwanted enantiomers of synthetically important alpha-hydroxyketones derived from kinetic resolution. (c) 2007 Elsevier Ltd. All rights reserved.
• Chiral dithiolane sulphoxides: An efficient stereoselective synthesis of (R) and (S)-3-benzoyloxy-2-butanone
  作者：M.Teresa Barros、Alcino J. Leitão、Christopher D. Maycock

  DOI：10.1016/0040-4039(95)01280-u

  日期：1995.9

  The effect of the addition of water on the asymmetric oxidation of an acyl dithiane and an acyl dithiolane has been studied. The use of enantiomerically pure dithiolane sulphoxides is demonstrated in a highly selective synthesis of (R)-3-benzoyloxy-2-butanone which depends upon a diastereoselective ketone reduction.