4-Hydroxy-2,3,4-trimethyl-5-methylene-cyclopent-2-enone | 127969-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-2,3,4-trimethyl-5-methylene-cyclopent-2-enone
• 英文别名: 4-Hydroxy-2,3,4-trimethyl-5-methylidenecyclopent-2-en-1-one
• CAS: 127969-09-9
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: WFMBPMGNFDYLOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-4-(trimethylsilyloxy)-3-penten-2-one 在 2,6-二甲基吡啶 、 正丁基锂 、 silica gel 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 5.75h， 生成 4-Hydroxy-2,3,4-trimethyl-5-methylene-cyclopent-2-enone
  参考文献：
  名称：

  Cyclopentannelation Reaction for Rapid Assembly of Multifunctional Products. (d,l)-Desepoxymethylenomycin a Methyl Ester

  摘要：

  The scope of the alkoxyallene cationic cyclopentannelation reaction has been examined. Non-hydrogen substituents at both C4 and C5 were required for synthetically useful yields. Whereas the cyclization appeared to be subject to steric constraints, it was relatively insensitive to electronic effects. An efficient synthesis of (d,l)- , desepoxymethylenomycin A methyl ester has been described.

  DOI：

  10.1080/00397919408011309

文献信息

• Densely functionalized cyclopentenones
  作者：Marcus A. Tius、Xiao-ming Zhou

  DOI：10.1016/s0040-4039(01)80760-7

  日期：1989.1
• TIUS, MARCUS A.;ZHOU, XIAO-MING, TETRAHEDRON LETT., 30,(1989) N5, C. 4629-4632
  作者：TIUS, MARCUS A.、ZHOU, XIAO-MING

  DOI：——

  日期：——
• Cyclopentannelation Reaction for Rapid Assembly of Multifunctional Products. (d,l)-Desepoxymethylenomycin a Methyl Ester
  作者：Marcus A. Tius、Chun-Kiu Kwok、Xue-Qin Gu、Chengwen Zhao

  DOI：10.1080/00397919408011309

  日期：1994.3

  The scope of the alkoxyallene cationic cyclopentannelation reaction has been examined. Non-hydrogen substituents at both C4 and C5 were required for synthetically useful yields. Whereas the cyclization appeared to be subject to steric constraints, it was relatively insensitive to electronic effects. An efficient synthesis of (d,l)- , desepoxymethylenomycin A methyl ester has been described.