(3-methyl-5-phenyl)-2-cyclopentenone | 69849-30-5

• 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: (3-methyl-5-phenyl)-2-cyclopentenone
• 英文别名: 3-Methyl-5-phenyl-2-cyclopenten-1-one；3-methyl-5-phenylcyclopent-2-en-1-one
• CAS: 69849-30-5
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: COKKKPKEKLIXHB-UHFFFAOYSA-N

物化性质

• 沸点：
  284.8±40.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙酮 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 (3-methyl-5-phenyl)-2-cyclopentenone
  参考文献：
  名称：

  Three-carbon annelations. Regiocontrolled reactivity of trimethylsilyl- and ethoxyethyl-protected cyanohydrins. Versatile homoenolate and acyl anion equivalents

  摘要：

  DOI：

  10.1021/jo01291a005

文献信息

• Synthesis of Cyclopentenones via Intramolecular HWE and the Palladium-Catalyzed Reactions of Allylic Hydroxy Phosphonate Derivatives
  作者：Bingli Yan、Christopher D. Spilling

  DOI：10.1021/jo8004028

  日期：2008.7.1

  Palladium-catalyzed decarboxylative rearrangement of nonracemic phosphono allylic acetoacetates, or the intermolecular allylic substitution of nonracemic phosphono allylic carbonates with tert-butyl acetoacetate followed by hydrolysis and decarboxylation, gave ω-ketovinyl phosphonates. A highly regioselective Wacker oxidation gave the ω,β-diketophosphonates which underwent intramolecular HWE reaction

  非外消旋膦酰基烯丙基乙酰乙酸的钯催化脱羧重排，或非乙酸膦酰基烯丙基碳酸酯的分子间烯丙基取代为乙酰乙酸叔丁酯，随后水解和脱羧，得到ω-酮乙烯基膦酸酯。高度区域选择性的Wacker氧化产生了ω，β-二酮膦酸酯，使其经历分子内HWE反应以生成非外消旋的环戊烯酮。导致膦酰基环戊烯酮的醛醇缩合与HWE反应竞争。环戊烯酮的立体化学和HWE与醛醇产物的比例取决于反应中所用碱的选择。
• Reaction of allylically substituted enolates with organometallic reagents: a convenient source of enolonium ion equivalents
  作者：Paul A. Wender、Jeanette M. Erhardt、Leo J. Letendre

  DOI：10.1021/ja00398a051

  日期：1981.4
• Rhodium(I)-Catalyzed Successive Double Cleavage of Carbon−Carbon Bonds of Strained Spiro Cyclobutanones
  作者：Masahiro Murakami、Kunio Takahashi、Hideki Amii、Yoshihiko Ito

  DOI：10.1021/ja971949x

  日期：1997.10.1
• Reinvestigation of the synthetic and mechanistic aspects of Mn(III) acetate mediated oxidation of enones
  作者：Ayhan S Demir、Ömer Reis、A Cigdem Igdir

  DOI：10.1016/j.tet.2004.02.039

  日期：2004.4

  Mn(OAc)(3) mediated alpha'-acetoxylation of alpha,beta-unsaturated enones is reinvestigated from a synthetic and mechanistic point of view and an improved procedure based on the use of acetic acid as a co-solvent is presented. Excellent results were obtained for a variety of structurally diverse and synthetically important enones under the optimized conditions. (C) 2004 Elsevier Ltd. All rights reserved.