3-methyl-4-oxononanoic acid | 109262-90-0

• 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: 3-methyl-4-oxononanoic acid
• CAS: 109262-90-0
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: DDKDAIWVRBQCNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-oxononanoic acid 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 baker's yeast 、 porcine pancreatic lipase 、 葡萄糖 、 tap water 作用下， 以 四氢呋喃 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 75.0h， 生成 (+)-(4S,5R)-5-acetoxy-4-methylnonanonitrile
  参考文献：
  名称：

  Baker's yeast-mediated approach to (−)-cis- and (+)-trans-Aerangis lactones

  摘要：

  The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00314-7
• 作为产物：
  描述：

  3-甲基-4-氧代-2-丁烯酸乙酯 在 XAD 1180 resin manganese(IV) oxide 、 氢氧化钾 、 baker's yeast 、 葡萄糖 、 tap water 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 3-methyl-4-oxononanoic acid
  参考文献：
  名称：

  Baker's yeast-mediated approach to (−)-cis- and (+)-trans-Aerangis lactones

  摘要：

  The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00314-7

文献信息

• Microbial bioreductions of γ- and δ-ketoacids and their esters
  作者：Cristina Forzato、Raffaella Gandolfi、Francesco Molinari、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(01)00184-7

  日期：2001.5

  best choice for the bioreduction of ethyl 2-oxocyclohexylacetate 2e, which afforded cis-(−)-5e and trans-(−)-5e with 98 and 99% e.e., respectively. Reduction of 3-(2-oxocyclohexyl)propionic acid 3e with Pichia glucozyma gave predominantly the corresponding δ-lactone trans-(−)-6e with 94% e.e., whose absolute configuration was determined by means of CD spectroscopy.

  一系列酵母被用于脂肪族和芳香族γ-和δ-酮酸和酯的生物还原中，以研究通过其相应的γ-和δ-羟基酸和酯的中间体制备对映体纯的γ-和δ-内酯。用刻氏毕赤酵母生物还原4-氧代壬酸乙酯2a可得到具有99％ee的γ-壬醇（+）- 5a，而事实证明，毕赤酵母是2-氧代环己基乙酸乙酯2e生物还原的最佳选择，后者可提供顺式-（- ）-5e和反式-（-）- 5e的ee分别为98％和99％。还原3-（2-氧代环己基）丙酸具有葡糖酵母的3e主要产生具有94％ee的相应的δ-内酯反式-（-）- 6e，其绝对构型是通过CD光谱法确定的。
• Enzymatic resolution of 3-substituted-4-oxoesters.
  作者：L. Blanco、G. Rousseau、J.-P. Barnier、E. Guibé-Jampel

  DOI：10.1016/s0957-4166(00)80116-0

  日期：1993.5

  The lipase catalyzed hydrolysis of cyanomethyl 3-substituted-4-oxoesters was studied. With 3-methyl substituted esters, PPL led to optically active compounds. When the 3-substituent was a larger group, more satisfactory results were obtained with PL, especially if the substituent attached to the ketone function is other from methyl.
• 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.
• TSUKASA, HIDETAKA, YUKAGAKU, 36,(1987) N 1, 51-53
  作者：TSUKASA, HIDETAKA

  DOI：——

  日期：——
• Baker's yeast-mediated approach to (−)-cis- and (+)-trans-Aerangis lactones
  作者：Elisabetta Brenna、Claudia Dei Negri、Claudio Fuganti、Stefano Serra

  DOI：10.1016/s0957-4166(01)00314-7

  日期：2001.7

  The first enantioselective synthesis of natural (-)-cis-Aerangis lactone (-)-1a and its (+)-trans-diastereoisomer (+)-lb is described. The key steps in the synthesis are: (i) the enantiospecific and 100% diastereoselective baker's yeast reduction of 1,4-keto acid 2, to afford enantiopure trans- cognac lactone (+)-10; (ii) the regioselective PPL-mediated hydrolysis of the primary acetate moiety of diacetate (+)-(3S,4R)-3, obtained from (+)-10. Chain elongation by one carbon atom via cyanide substitution, and inversion of the configuration of C(5) in nitrile derivative (+)-21a are also required to complete the synthetic route to (-)-1a. (C) 2001 Elsevier Science Ltd. All rights reserved.