ethyl 3-(5-(1,1-dimethylethyl)-2-oxocyclohexyl)propanoate | 111248-48-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 3-(5-(1,1-dimethylethyl)-2-oxocyclohexyl)propanoate
• 英文别名: (cis/trans)-ethyl 3-(5-(1,1-dimethylethyl)-2-oxo-cyclohexyl)propionate；Ethyl 3-(5-tert-butyl-2-oxocyclohexyl)propanoate
• CAS: 111248-48-7
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: DGFMWHFQQQQHBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(5-(1,1-dimethylethyl)-2-oxocyclohexyl)propanoate 在 baker's yeast 、 水 作用下， 生成 (+/-)-cis-6-(1,1-dimethylethyl)-octahydro-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Baker's yeast reduction of cyclic δ-ketoesters: synthesis and chiroptical properties of condensed δ-lactones

  摘要：

  Enantiomerically pure condensed delta-lactones have been prepared from the corresponding delta-ketoesters by the use of Saccharomyces cerevisiae. The reactions were not only highly enantioselective but also highly diastereoselective, provided the baker's yeast was preincubated at 50 degrees C for 30 min. Interestingly, and contrary to what is usually found, the use of nutrients inhibited the bioreductions. The relative configurational assignments have been made by means of NMR, while the absolute configurations and conformations of the lactone rings were attributed by means of CD studies. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00098-1
• 作为产物：
  描述：

  1-[4-(叔-丁基)-1-环己烯-1-基]吡咯烷 、 丙烯酸乙酯 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 ethyl 3-(5-(1,1-dimethylethyl)-2-oxocyclohexyl)propanoate
  参考文献：
  名称：

  Baker's yeast reduction of cyclic δ-ketoesters: synthesis and chiroptical properties of condensed δ-lactones

  摘要：

  Enantiomerically pure condensed delta-lactones have been prepared from the corresponding delta-ketoesters by the use of Saccharomyces cerevisiae. The reactions were not only highly enantioselective but also highly diastereoselective, provided the baker's yeast was preincubated at 50 degrees C for 30 min. Interestingly, and contrary to what is usually found, the use of nutrients inhibited the bioreductions. The relative configurational assignments have been made by means of NMR, while the absolute configurations and conformations of the lactone rings were attributed by means of CD studies. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00098-1

文献信息

• Podraza, Kenneth F., Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 293 - 295
  作者：Podraza, Kenneth F.

  DOI：——

  日期：——
• Synthesis of enantiomerically pure bicyclic condensed δ-lactones via microbial reduction and enzymic resolution strategies
  作者：Erica Fogal、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(00)00218-4

  日期：2000.6

  The formation of enantiopure delta-lactones condensed with alicyclic rings has been achieved either by reduction with baker's yeast of the corresponding delta-keto esters and delta-keto acids or by enzymic resolution of the former compounds. The absolute configurations of the lactones were determined by means of CD spectroscopy, using the correlation method. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Baker's yeast reduction of cyclic δ-ketoesters: synthesis and chiroptical properties of condensed δ-lactones
  作者：Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(99)00098-1

  日期：1999.4

  Enantiomerically pure condensed delta-lactones have been prepared from the corresponding delta-ketoesters by the use of Saccharomyces cerevisiae. The reactions were not only highly enantioselective but also highly diastereoselective, provided the baker's yeast was preincubated at 50 degrees C for 30 min. Interestingly, and contrary to what is usually found, the use of nutrients inhibited the bioreductions. The relative configurational assignments have been made by means of NMR, while the absolute configurations and conformations of the lactone rings were attributed by means of CD studies. (C) 1999 Elsevier Science Ltd. All rights reserved.