cis-2-Trifluoromethyl-4-methyl-γ-lactone | 156942-97-1

• 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: cis-2-Trifluoromethyl-4-methyl-γ-lactone
• 英文别名: (3S,5R)-5-methyl-3-(trifluoromethyl)oxolan-2-one
• CAS: 156942-97-1
• 化学式: C₆H₇F₃O₂
• 分子量: 168.116
• InChiKey: QYTOOVCITOVYEL-DMTCNVIQSA-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：

  cis-2-Trifluoromethyl-4-methyl-γ-lactone 在 吡啶 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (3S,5R)-2-<(4'''-Hexyloxybiphenyl)-4''-carbonyloxy>-3-trifluoromethyl-5-methyltetrahydrofuran
  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

• A cyclization reaction catalysed by antibodies
  作者：Tomoya Kitazume、Mitsunori Takeda

  DOI：10.1039/c39950000039

  日期：——

  Monoclonal antibodies, elicited by transition-state analogues for either exo- or endo-lactonization of α-trifluoromethyl-γ,δ-unsaturated acids, catalyse the regiospecific formation of corresponding γ- or δ-lactones; the exo-lactonization proceeds with high diastereospecificity.

  单克隆抗体在α-三氟甲基-γ,δ-不饱和酸的外-或内-内酯化过渡态类似物的诱导下，催化形成相应的γ-或δ-内酯的区域特异性；外-内酯化过程具有高度的非对映特异性。
• 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.