trans-2-Trifluoromethyl-4-methyl-γ-lactone

• 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: trans-2-Trifluoromethyl-4-methyl-γ-lactone
• 英文别名: trans-dihydro-5-methyl-3-trifluoromethyl-2(3H)-furanone；5-methyl-3-(trifluoromethyl)dihydrofuran-2(3H)-one；(3R,5R)-5-methyl-3-(trifluoromethyl)oxolan-2-one
• 化学式: C₆H₇F₃O₂
• 分子量: 168.116
• InChiKey: QYTOOVCITOVYEL-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  trans-2-Trifluoromethyl-4-methyl-γ-lactone 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 6.0h， 以77%的产率得到(3S,5S)-2-Hydroxy-5-methyl-3-trifluoromethyltetrahydrofuran
  参考文献：
  名称：

  Synthesis of optically active γ-lactones and dopants for ferroelectric liquid crystals possessing a trifluoromethyl group

  摘要：

  A series of trans- and cis-gamma-lactones with high optical purity have been prepared from the lactonization of (S)-(-)-2-(trifluoromethyl)-4-pentenoic acid (>94% ee) under acidic conditions. These materials have been transformed into new types of dopant for ferroelectric liquid crystals possessing a trifluoromethyl group.

  DOI：

  10.1016/0022-1139(93)02948-e
• 作为产物：
  描述：

  2-trifluoromethyl-4-pentenoic acid 在 硫酸 作用下， 反应 5.0h， 生成 cis-2-Trifluoromethyl-4-methyl-γ-lactone 、 trans-2-Trifluoromethyl-4-methyl-γ-lactone
  参考文献：
  名称：

  Synthesis of optically active γ-lactones and dopants for ferroelectric liquid crystals possessing a trifluoromethyl group

  摘要：

  A series of trans- and cis-gamma-lactones with high optical purity have been prepared from the lactonization of (S)-(-)-2-(trifluoromethyl)-4-pentenoic acid (>94% ee) under acidic conditions. These materials have been transformed into new types of dopant for ferroelectric liquid crystals possessing a trifluoromethyl group.

  DOI：

  10.1016/0022-1139(93)02948-e

文献信息

• Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol
  作者：Chenxiao Qi、Shengwen Yang、Vincent Gandon、David Lebœuf

  DOI：10.1021/acs.orglett.9b02705

  日期：2019.9.20

  hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist

  我们报告了未活化烯烃的有效分子内氢酰氧基化作用，提供了对相关γ-内酯的流线型通道，其特征在于利用了钙盐（II）或三氟甲酰亚胺作为六氟异丙醇中的催化剂。该方法可用于天然产物的合成以及天然和生物活性分子的后期功能化。此外，DFT计算用于阐明在未活化烯烃的加氢酰胺化和加氢酰氧基化之间有关5和6元环形成的反应性扭曲。
• Synthesis of α-trifluoromethyl unsaturated acids and derivatives
  作者：Frédérique Tellier、Max Audouin、Raymond Sauvêtre

  DOI：10.1016/s0022-1139(01)00542-5

  日期：2002.2

  A one pot synthesis of alpha-trifluoromethyl unsaturated acids via a [3,3]-sigmatropic rearrangement of allyl (or propargyl) fluorovinyl ethers is described. By proto- and iodolactonization. these acids lead to the corresponding trifluoromethylated lactones. (C) 2002 Elsevier Science B.V.. All rights reserved.
• Synthesis of optically active γ-lactones and dopants for ferroelectric liquid crystals possessing a trifluoromethyl group
  作者：Shoji Watanabe、Yuji Sakai、Mitsunori Takeda、Tomoya Kitazume、Takashi Yamazaki

  DOI：10.1016/0022-1139(93)02948-e

  日期：1994.5

  A series of trans- and cis-gamma-lactones with high optical purity have been prepared from the lactonization of (S)-(-)-2-(trifluoromethyl)-4-pentenoic acid (>94% ee) under acidic conditions. These materials have been transformed into new types of dopant for ferroelectric liquid crystals possessing a trifluoromethyl group.