(3Z,5E)-4-methyl-hepta-3,5-dien-2-one | 29178-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z,5E)-4-methyl-hepta-3,5-dien-2-one
• 英文别名: (3Z,5E)-4-methylhepta-3,5-dien-2-one
• CAS: 29178-98-1
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: CLLAEQBTPCCTBI-DEQVHDEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3Z,5E)-4-methyl-hepta-3,5-dien-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以84%的产率得到(3Z,5E)-4-methylhepta-3,5-dien-2-ol
  参考文献：
  名称：

  Highly Like-Selective [4 + 2] Cycloadditions of Chiral Dienols: The Importance of 1,3-Allylic Strain in the Hydroxy-Directed Stereocontrol

  摘要：

  The chiral open-chain dienols 3a,b, which possess 1,3-allylic strain due to the presence of a cis substituent, give with the dienophiles maleic anhydride (MA), N-phenyl maleimide (NPM), 4-phenyl- (PTAD), and 4-methyl-1,2,4-triazoline-3,5-dione (MTAD) the corresponding [4 + 2] cycloadducts in very good yields and with high like selectivity. In contrast to previous reports on dienols without 1,3-allylic strain, the sense of diastereoselectivity does not vary with the dienophile type. The cis substituent aligns preferred conformations in the ground and transition states for which the hydrogen atom is placed in the sterically most biased inside position. Sterically and electronically controlled dienophile attack on these rotamers leads to the observed like stereochemistry. The participation of electronic features, most prominently hydroxy-directed stereocontrol, is substantiated by solvent effects in the triazolinedione cycloadditions, i.e., lower pi-facial selectivities are observed in polar solvents. The present results demonstrate the efficacy of 1,3-allylic strain in promoting conformational preferences in [4 + 2] cycloadditions with asymmetric dienols.

  DOI：

  10.1021/ja00141a010
• 作为产物：
  描述：

  hydroxy-6 methyl-4 heptene-4 one-2 (E) 生成 (3Z,5E)-4-methyl-hepta-3,5-dien-2-one
  参考文献：
  名称：

  LHOSTE, P.;MOREAU, M.;DREUX, J., TETRAHEDRON, 1984, 40, N 9, 1551-1561

  摘要：

  DOI：

文献信息

• Action des composes organomagnesiens sur les pyrones-2-VII
  作者：P. Lhoste、M. Moreau、J. Dreux

  DOI：10.1016/s0040-4020(01)91804-6

  日期：1984.1

  In the reaction between organomagnesium compounds and 2-pyrones, the relative stability of the 6-hydroxy 5,6-dihydro 2H-pyrans and their tautomeric forms (ketols) has no influence on the reaction pathway. When ethylenic ketols are obtained, the corresponding tautomeric dihydropyranols are prepared in a selective way by reaction of nucleophilic reagents on the 3,6-dihydro-2-pyrones. In the other hand

  在有机镁化合物与2-吡喃酮之间的反应中，6-羟基5,6-二氢2H-吡喃及其互变异构形式（酮醇）的相对稳定性对反应途径没有影响。当获得烯属酮醇时，通过亲核试剂在3，6-二氢-2-吡喃酮上的反应选择性地制备相应的互变异构二氢吡喃醇。另一方面，在这两个反应过程中，二氢吡喃酚或不饱和酮醇E的排他性形成表明，在实验条件下，这两个实体之间没有平衡。
• Tricarbonyl (trans-.pi.-pentadienyl)iron cations. Solvolysis stereochemistry
  作者：Donald E. Kuhn、C. Peter Lillya

  DOI：10.1021/ja00760a042

  日期：1972.3
• Safieddine,A. et al., Bulletin de la Societe Chimique de France, 1972, p. 2510 - 2513
  作者：Safieddine,A. et al.

  DOI：——

  日期：——
• Duperrier,A. et al., Bulletin de la Societe Chimique de France, 1975, p. 2307 - 2312
  作者：Duperrier,A. et al.

  DOI：——

  日期：——
• ANDERSON C. D.; SHARP J. T.; SOOD H. R.; STRATHDEE R. S., J. CHEM. SOC. CHEM. COMMUNS <CCOM-A8>, 1975, NO 15, 613-614
  作者：ANDERSON C. D.、 SHARP J. T.、 SOOD H. R.、 STRATHDEE R. S.

  DOI：——

  日期：——