α-[3'-(trifluoromethyl)benzyl]-γ-butyrolactone

• 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-[3'-(trifluoromethyl)benzyl]-γ-butyrolactone
• 英文别名: α-(3-trifluoromethylbenzyl)-γ-butyrolactone；3-(3-(trifluoromethyl)benzyl)dihydrofuran-2(3H)-one；3-[[3-(Trifluoromethyl)phenyl]methyl]oxolan-2-one
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: OGQIHZZILNWGLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-[3'-(trifluoromethyl)benzyl]-γ-butyrolactone 在 二异丁基氢化铝 、 rochelle salt 作用下， 以 甲苯 、 水 为溶剂， 生成
  参考文献：
  名称：

  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters

  摘要：

  A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to alpha-amino and alpha-oxy ketones and derivatives thereof.

  DOI：

  10.1021/acs.orglett.5b02833
• 作为产物：
  描述：

  γ-丁内酯 、 3-(三氟甲基)溴苄 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以74%的产率得到α-[3'-(trifluoromethyl)benzyl]-γ-butyrolactone
  参考文献：
  名称：

  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters

  摘要：

  A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to alpha-amino and alpha-oxy ketones and derivatives thereof.

  DOI：

  10.1021/acs.orglett.5b02833

文献信息

• Palladium-Catalyzed Arylation of α-Methylene-γ-butyrolactone:  3-Benzylfuran-2(5<i>H</i>)-ones vs (<i>Z</i>)-Benzylidene-γ-butyrolactones and Their Reduction to 3-Benzyl-γ-butyrolactones
  作者：Antonio Arcadi、Marco Chiarini、Fabio Marinelli、Zoltán Berente、Làszlò Kollàr

  DOI：10.1021/ol9912130

  日期：2000.1.1

  [GRAPHICS]The palladium-catalyzed arylation of the alpha-methylene-gamma-butyrolactone proceeds in good yields and may be directed toward the synthesis of 3-benzylfuran-2(5H)-ones when the starting aryl iodides contain strongly electron withdrawing groups. The combined palladium-catalyzed arylation/hydrogenation of the alpha-methylene-gamma-butyrolactone represents a new simple entry into functionalized alpha-benzyl-gamma-butyrolactones.
• Palladium-Catalysed Vinylic Substitution of Aryl/Vinyl Iodides and Triflates with α-Methylene-γ-butyrolactone − An Application to the Synthesis of 3-Alkyl-γ-Butyrolactones through Combined Palladium-Catalysed Coupling/Hydrogenation Reactions
  作者：Antonio Arcadi、Marco Chiarini、Fabio Marinelli、Zoltán Berente、László Kollár

  DOI：10.1002/1099-0690(200108)2001:16<3165::aid-ejoc3165>3.0.co;2-6

  日期：2001.8
• Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters
  作者：Barbara J. Casavant、Zainab M. Khoder、Ilyas A. Berhane、Sherry R. Chemler

  DOI：10.1021/acs.orglett.5b02833

  日期：2015.12.18

  A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to alpha-amino and alpha-oxy ketones and derivatives thereof.