methyl (E)-5-(2-methyl-1,3-dioxocyclohexyl)-2-pentenoate | 909726-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E)-5-(2-methyl-1,3-dioxocyclohexyl)-2-pentenoate
• 英文别名: methyl (E)-5-(1-methyl-2,6-dioxocyclohexyl)pent-2-enoate；(e)-Methyl 5-(1-methyl-2,6-dioxocyclohexyl)pent-2-enoate
• CAS: 909726-56-3
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: VICWNKHKILNAGR-FPYGCLRLSA-N

物化性质

• 沸点：
  365.0±22.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-5-(2-methyl-1,3-dioxocyclohexyl)-2-pentenoate 在 吡啶 、 baker's yeast 、 蔗糖 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 50.0h， 生成 (E)-5-((1R,2S)-2-Acetoxy-1-methyl-6-oxo-cyclohexyl)-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  An efficient route for the synthesis of methyl (−)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate by using baker’s yeast-catalyzed asymmetric reduction

  摘要：

  Methyl (-)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate 1, a key synthetic intermediate for the synthesis of terpenoids, was efficiently synthesized by using a baker's yeast-catalyzed asymmetric reduction of a sigma-symmetrical 1,3-cyclohexanedione derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.015
• 作为产物：
  描述：

  2-甲基-1,3-环己二酮 生成 methyl (E)-5-(2-methyl-1,3-dioxocyclohexyl)-2-pentenoate
  参考文献：
  名称：

  Inversion of Diastereoselectivity Depending on Substrate Concentration in ­Baker’s Yeast Catalyzed Reduction of σ-Symmetrical 1,3-Cyclopentadiones and 1,3-Cyclohexadiones

  摘要：

  在面包酵母催化的β-对称性2,2-二烷基环戊烷-1,3-二酮1,2和环己烷-1,3-二酮20的还原反应中，首次观察到了由于底物浓度变化而导致的非对映选择性反转。随着底物浓度从8 mM增加到40 mM，选择性逐渐发生变化。同时，当在高底物浓度（40 mM）下进行反应时，酵母催化的还原反应应用于1的氢化产物（5）时，可以高产率得到单一非对映异构体。

  DOI：

  10.1055/s-2006-949647

文献信息

• Efficient Construction of Polycyclic Derivatives via a Highly Selective Cu^I-Catalyzed Domino Reductive-Aldol Cyclization
  作者：Julia Deschamp、Olivier Riant

  DOI：10.1021/ol802879f

  日期：2009.3.19

  A versatile methodology for the diastereo- and enantioselective domino reductive-aldol cyclizations is reported. By using a copper (I)/diphosphane ligand, various five- and six-membered rings were generated with good to excellent diastereo- and enantioselectivities (cis:trans up to 100:0 and ee up to 95%).
• An efficient route for the synthesis of methyl (−)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate by using baker’s yeast-catalyzed asymmetric reduction
  作者：Takahiro Katoh、Shinsuke Mizumoto、Masato Fudesaka、Masatoshi Takeo、Tetsuya Kajimoto、Manabu Node

  DOI：10.1016/j.tetasy.2006.06.015

  日期：2006.7

  Methyl (-)-1,4a-dimethyl-5-oxodecahydronaphthalene-1-carboxylate 1, a key synthetic intermediate for the synthesis of terpenoids, was efficiently synthesized by using a baker's yeast-catalyzed asymmetric reduction of a sigma-symmetrical 1,3-cyclohexanedione derivative. (c) 2006 Elsevier Ltd. All rights reserved.
• Inversion of Diastereoselectivity Depending on Substrate Concentration in ­Baker’s Yeast Catalyzed Reduction of σ-Symmetrical 1,3-Cyclopentadiones and 1,3-Cyclohexadiones
  作者：Manabu Node、Takahiro Katoh、Shinsuke Mizumoto、Masato Fudesaka、Yuki Nakashima、Tetsuya Kajimoto

  DOI：10.1055/s-2006-949647

  日期：2006.9

  Inversion of diastereoselectivity caused by a change in substrate concentration was first observed in baker’s yeast catalyzed reduction of σ-symmetrical 2,2-dialkylated cyclopentan-1,3-diones 1,2 and cyclohexan-1,3-dione 20. The selectivity altered by degrees depending on the substrate concentration from 8 mM to 40 mM. Meanwhile, application of the yeast-catalyzed reduction to the hydrogenated compound (5) of 1 afforded a single diastereomer in good yield when the reaction was conducted in high substrate ­concentration (40 mM).

  在面包酵母催化的β-对称性2,2-二烷基环戊烷-1,3-二酮1,2和环己烷-1,3-二酮20的还原反应中，首次观察到了由于底物浓度变化而导致的非对映选择性反转。随着底物浓度从8 mM增加到40 mM，选择性逐渐发生变化。同时，当在高底物浓度（40 mM）下进行反应时，酵母催化的还原反应应用于1的氢化产物（5）时，可以高产率得到单一非对映异构体。