ethyl (R)-(+)-3-methyl-4-oxononanoate | 344798-50-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl (R)-(+)-3-methyl-4-oxononanoate
• 英文别名: (R)-ethyl 3-methyl-4-oxononanoate；ethyl (3R)-3-methyl-4-oxononanoate
• CAS: 344798-50-1
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: SMJQOCFRGMBQGT-SNVBAGLBSA-N

物化性质

• 沸点：
  289.1±13.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  ethyl (R)-(+)-3-methyl-4-oxononanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到(R)-4-Methyl-5-pentyl-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies

  摘要：

  Both enantiomers of the diastereomeric cognac lactones have been synthesised using enzyme assisted reactions in the enantiodifferentiating step. This was accomplished by baker's yeast reduction of their precursors 3-methyl-4-oxononanoic acid and ester and by enzymatic hydrolysis of the latter. An inhibition of hydrolases by the products was observed. Trans-(+)-, trans-(-)-, cis-(+)- and cis-(-)-cognac lactones having 99, 88, 88 and 99% e.e., respectively, were thus obtained. Their CD spectra have also been studied. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00059-3
• 作为产物：
  描述：

  2-丁烯酸乙酯 在 Porcine Pancreas Lipase 、 过氧化苯甲酰 作用下， 反应 10.0h， 生成 ethyl (R)-(+)-3-methyl-4-oxononanoate
  参考文献：
  名称：

  Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies

  摘要：

  Both enantiomers of the diastereomeric cognac lactones have been synthesised using enzyme assisted reactions in the enantiodifferentiating step. This was accomplished by baker's yeast reduction of their precursors 3-methyl-4-oxononanoic acid and ester and by enzymatic hydrolysis of the latter. An inhibition of hydrolases by the products was observed. Trans-(+)-, trans-(-)-, cis-(+)- and cis-(-)-cognac lactones having 99, 88, 88 and 99% e.e., respectively, were thus obtained. Their CD spectra have also been studied. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00059-3

文献信息

• Enantioselective, Catalytic One‐Pot Synthesis of <i>γ</i> ‐Butyrolactone‐Based Fragrances
  作者：Ceyda Kumru、Thomas Classen、Jörg Pietruszka

  DOI：10.1002/cctc.201801040

  日期：2018.11.7

  Herein the preparative (1 g scale), stereoselective syntheses of various alkyl‐substituted γ‐butyrolactone fragrances 1 is described. The α,β‐unsaturated γ‐keto esters 2 as starting materials were synthesized by a Horner‐Wadsworth‐Emmons reaction and are further reduced by an ene reductase and alcohol dehydrogenase in a one‐pot enzyme cascade to nine desired γ‐butyrolactones 1, among them whisky (1 c)

  本文描述了各种烷基取代的γ-丁内酯香料1的制备（1 g规模）的立体选择性合成。以Horner-Wadsworth-Emmons反应合成作为原料的α，β-不饱和γ-酮酸酯2，并通过单罐酶级联反应中的烯还原酶和醇脱氢酶进一步将其还原为九种所需的γ-丁内酯1，其中威士忌（1 c）和白兰地内酯（1 d）。产品1以中等至良好的收率和非常好的非对映选择性获得了C。此外，对n Bu取代基的位置进行了置换，以研究其对酶级联反应的影响。
• A chemoenzymatic synthesis of optically active aza analogues of Quercus lactones
  作者：Fulvia Felluga、Valentina Gombac、Michela Pavan、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2003.10.014

  日期：2004.1

  The synthesis of optically active 4-methyl-5-n-butyl- and 5-n-pentylpyrrolidin-2-ones, aza analogues of the corresponding Quercus lactones, has been achieved by a chemoenzymatic procedure, involving in the enantiodifferentiating step the enzymatic kinetic resolution of the corresponding γ-ketoester precursors, followed by reductive amination and subsequent cyclization of the enantiomerically pure hydrolysis

  光学活性的4-甲基-5-正丁基和5-正戊基吡咯烷二-2-酮（相应的栎内酯的氮杂类似物）的合成已通过化学酶促方法完成，该化学酶促方法包括在对映异构步骤中进行酶促动力学。拆分相应的γ-酮酸酯前体，然后进行还原胺化，然后将对映体纯水解产物环化。还研究了反应条件的影响以及底物结构对酶水解的影响。
• Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies
  作者：Fabio Benedetti、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin、Michela Vicario

  DOI：10.1016/s0957-4166(01)00059-3

  日期：2001.3

  Both enantiomers of the diastereomeric cognac lactones have been synthesised using enzyme assisted reactions in the enantiodifferentiating step. This was accomplished by baker's yeast reduction of their precursors 3-methyl-4-oxononanoic acid and ester and by enzymatic hydrolysis of the latter. An inhibition of hydrolases by the products was observed. Trans-(+)-, trans-(-)-, cis-(+)- and cis-(-)-cognac lactones having 99, 88, 88 and 99% e.e., respectively, were thus obtained. Their CD spectra have also been studied. (C) 2001 Elsevier Science Ltd. All rights reserved.