2-diethoxymethyl-oct-1-en-3-one | 98698-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-diethoxymethyl-oct-1-en-3-one
• 英文别名: 2-(Diethoxymethyl)oct-1-en-3-one
• CAS: 98698-52-3
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: UGTYUTJDMKPQJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-diethoxymethyl-oct-1-en-3-one 在 baker's yeast 、 葡萄糖 、 tap water 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以52%的产率得到(E)-1-Ethoxy-2-methyl-oct-1-en-3-one
  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：

  2-diethoxymethyl-oct-1-en-3-ol 以65%的产率得到2-diethoxymethyl-oct-1-en-3-one
  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

• Synthesis of 1,1-Diethoxy-2-methylene-3-oxoalkanes(α-Methylene-β-oxoacetals)
  作者：J. C. Depezay、Y. Le Merrer、M. Saniere

  DOI：10.1055/s-1985-31340

  日期：——
• Ethers d'enols β-cetoniques : synthese et reactivite vis-a-vis d'organolithiens
  作者：Jean-Claude Depezay、Michéle Saniere

  DOI：10.1016/s0040-4020(01)96549-4

  日期：1985.1
• DEPEZAY, J. -C.;SANIERE, M., TETRAHEDRON, 1985, 41, N 10, 1869-1875
  作者：DEPEZAY, J. -C.、SANIERE, M.

  DOI：——

  日期：——
• DEPEZAY, J. C.;LE, MERRER, Y.;SANIERE, M., SYNTHESIS, BRD, 1985, N 8, 766-768
  作者：DEPEZAY, J. C.、LE, MERRER, Y.、SANIERE, M.

  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.