(R)-4,5-dimethyl-4-p-tolylcyclopentenone | 169305-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4,5-dimethyl-4-p-tolylcyclopentenone
• 英文别名: (4R,5R)-4,5-dimethyl-4-(4-methylphenyl)cyclopent-2-en-1-one
• CAS: 169305-53-7
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: TUTDFQMVLQURPU-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-4,5-dimethyl-4-p-tolylcyclopentenone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到(2R,3R)-2,3-dimethyl-3-p-tolylcyclopentanone
  参考文献：
  名称：

  Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene

  摘要：

  The chiral bicyclic lactam 5, previously reported in the synthesis of(-)-alpha-cuparenone, was used to construct the more complex title compound 2. A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess. Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.

  DOI：

  10.1021/jo00125a042
• 作为产物：
  描述：

  (R)-4,5-dimethyl-4-p-tolylcyclopentenol 在 jones reagent 作用下， 以 丙酮 为溶剂， 以99%的产率得到(R)-4,5-dimethyl-4-p-tolylcyclopentenone
  参考文献：
  名称：

  Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene

  摘要：

  The chiral bicyclic lactam 5, previously reported in the synthesis of(-)-alpha-cuparenone, was used to construct the more complex title compound 2. A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess. Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.

  DOI：

  10.1021/jo00125a042

文献信息

• Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene
  作者：Jacob B. Schwarz、A. I. Meyers

  DOI：10.1021/jo00125a042

  日期：1995.10

  The chiral bicyclic lactam 5, previously reported in the synthesis of(-)-alpha-cuparenone, was used to construct the more complex title compound 2. A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess. Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.