α, α-diphenyl-γ-methylidene-δ-valerolactone | 1198581-74-6

• 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: α, α-diphenyl-γ-methylidene-δ-valerolactone
• 英文别名: 5-Methylidene-3,3-diphenyloxan-2-one；5-methylidene-3,3-diphenyloxan-2-one
• CAS: 1198581-74-6
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: ZJIKPGWVHZTLCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  α, α-diphenyl-γ-methylidene-δ-valerolactone 在 allyl(cyclopentadiene)palladium(II) 、 sodium methylate 、 N,N-diisopropyldibenzo[d,f][1,3,2]dioxaphosphepin-6-amine 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.0h， 生成 Methyl 4-[[2-hydroxyethyl-(4-methylphenyl)sulfonylamino]methyl]-2,2-diphenylpent-4-enoate
  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：

  二苯基乙酸甲酯 、 碳酸二甲酯 、 2-(tert-butyldimethylsiloxy)methyl-2-propen-1-yl methanesulfonate 在 sodium hydride 、 四丁基氟化铵 作用下， 以 mineral oil 、 四氢呋喃 为溶剂， 反应 47.4h， 以47%的产率得到α, α-diphenyl-γ-methylidene-δ-valerolactone
  参考文献：
  名称：

  Palladium-Catalyzed Decarboxylative [4 + 3] Cyclization of γ-Methylidene-δ-valerolactones with 1,1-Dicyanocyclopropanes

  摘要：

  A palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes has been developed to produce cycloheptane derivatives in a convergent manner. This method can be applied to the synthesis of azepanes by reacting with aziridines, and their asymmetric variants have also been described. In addition, selective ring-expansion reactions can be achieved for certain gamma-methylidene-delta-valerolactones to give nondecarboxylated nine-membered lactones.

  DOI：

  10.1021/ol902326s