α-methyl-α-phenyl-γ-methylidene-δ-valerolactone | 1306830-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α-methyl-α-phenyl-γ-methylidene-δ-valerolactone
• 英文别名: 3-Methyl-5-methylidene-3-phenyloxan-2-one
• CAS: 1306830-30-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: YDNNVQPIKAPEJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲苯磺酰基氮杂环丙烷 、 α-methyl-α-phenyl-γ-methylidene-δ-valerolactone 在 allyl(cyclopentadiene)palladium(II) 、 N,N-diisopropyldibenzo[d,f][1,3,2]dioxaphosphepin-6-amine 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到8-Methyl-6-methylidene-4-(4-methylphenyl)sulfonyl-8-phenyl-1,4-oxazonan-9-one
  参考文献：
  名称：

  Synthesis of Nine-Membered Azlactones by Palladium-Catalyzed Ring-Expansion of γ-Methylidene-δ-valerolactones with Aziridines

  摘要：

  A palladium-catalyzed formal [6 + 3] cyclization of gamma-methylidene-delta-valerolactones with aziridines has been developed to produce 1,4-oxazonan-9-ones, a class of nine-membered azlactones that are not easily accessible by existing methods. The products thus obtained can also be further functionalized with ease.

  DOI：

  10.1021/jo2006158
• 作为产物：
  描述：

  2-苯基丙酸 在 氯化亚砜 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 47.5h， 生成 α-methyl-α-phenyl-γ-methylidene-δ-valerolactone
  参考文献：
  名称：

  Synthesis of Nine-Membered Azlactones by Palladium-Catalyzed Ring-Expansion of γ-Methylidene-δ-valerolactones with Aziridines

  摘要：

  A palladium-catalyzed formal [6 + 3] cyclization of gamma-methylidene-delta-valerolactones with aziridines has been developed to produce 1,4-oxazonan-9-ones, a class of nine-membered azlactones that are not easily accessible by existing methods. The products thus obtained can also be further functionalized with ease.

  DOI：

  10.1021/jo2006158