(3R)-Tetrahydro-4,4-dimethyl-2-oxo-fur-3-yl 2-(trifluoromethyl)propenoate | 131758-77-5

• 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: (3R)-Tetrahydro-4,4-dimethyl-2-oxo-fur-3-yl 2-(trifluoromethyl)propenoate
• 英文别名: D-pantolactone 2-trifluoromethylpropenoate；[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] 2-(trifluoromethyl)prop-2-enoate
• CAS: 131758-77-5
• 化学式: C₁₀H₁₁F₃O₄
• 分子量: 252.19
• InChiKey: AQLSGZXUXZHJNP-LURJTMIESA-N

物化性质

• 沸点：
  314.6±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R)-Tetrahydro-4,4-dimethyl-2-oxo-fur-3-yl 2-(trifluoromethyl)propenoate 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 四氯化钛 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 5-Ethyl-2-trifluoromethyl-heptanoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  路易斯酸催化的2-三氟甲基丙酸的酯的烯反应

  摘要：

  在酯（路易斯酸催化的烯反应1和2的2-trifluoromethylpropenoic酸，的高反应性）1个2以及制备光学活性的三氟甲基化的叔碳的（小号通过的TiCl -构型，> 80％非对映体过量）4据报道，催化的烯反应为2。

  DOI：

  10.1039/c39910000721
• 作为产物：
  描述：

  2-(trifluoromethyl)acrylic chloride 、 D-(-)-泛酰内酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到(3R)-Tetrahydro-4,4-dimethyl-2-oxo-fur-3-yl 2-(trifluoromethyl)propenoate
  参考文献：
  名称：

  Construction of trifluoromethylated quaternary carbons via Diels-Alder reactions of 2-(trifluoromethyl)propenoic acid derivatives: application to the synthesis of 16,16,16-trifluororetinal

  摘要：

  Diels-Alder reactions of 2-(trifluoromethyl)propenoic acid (1) and its 2,2,2-trifluoroethyl ester 2 with various dienes gave adducts in good yields. In Lewis acid catalyzed Diels-Alder reactions of 2, the combination of the Lewis acid and solvent proved to be crucial. For example, polymerization occurred in the case of TiCl4-CH2Cl2 and adduct formation was observed with TiCl4-toluene and TiCl2(O-i-Pr)2-CH2Cl2. In the TiCl4-catalyzed Diels-Alder reaction of the 2-(trifluoromethyl)propenoate ester 3 of D-pantolactone with butadiene, the formation of the R configurational quaternary carbon bearing the trifluoromethyl group was confirmed by X-ray crystallographic analysis of the adduct 20. No polymerization of ester 3 could be detected in the presence of TiCl4 in CH2Cl2. The reactivity difference between 2 and 3 in TiCl4-catalyzed Diels-Alder reactions may possibly be attributable to the stabilization of the 3-TiCl4 complex or weakening of Lewis acidity by coordination of the bidentate ester group of 3. The synthesis of all-trans-16,16,16-trifluororetinal (4), which is considered to be an important analogue for the study of retinal-binding protein, was conducted on the basis of these results. Comparison of the absorption maximum (362 nm) of 4 with other trifluororetinal 34 (362 nm) and 35 (382 nm) reported previously suggests the possibility of a large torsion of the conjugated system between the ring and the polyenal side chain in 4.

  DOI：

  10.1021/jo00005a014

文献信息

• Construction of trifluoromethylated quaternary carbons via Diels-Alder reactions of 2-(trifluoromethyl)propenoic acid derivatives: application to the synthesis of 16,16,16-trifluororetinal
  作者：Yuji Hanzawa、Makoto Suzuki、Yoshiro Kobayashi、Takeo Taguchi、Yoichi Iitaka

  DOI：10.1021/jo00005a014

  日期：1991.3

  Diels-Alder reactions of 2-(trifluoromethyl)propenoic acid (1) and its 2,2,2-trifluoroethyl ester 2 with various dienes gave adducts in good yields. In Lewis acid catalyzed Diels-Alder reactions of 2, the combination of the Lewis acid and solvent proved to be crucial. For example, polymerization occurred in the case of TiCl4-CH2Cl2 and adduct formation was observed with TiCl4-toluene and TiCl2(O-i-Pr)2-CH2Cl2. In the TiCl4-catalyzed Diels-Alder reaction of the 2-(trifluoromethyl)propenoate ester 3 of D-pantolactone with butadiene, the formation of the R configurational quaternary carbon bearing the trifluoromethyl group was confirmed by X-ray crystallographic analysis of the adduct 20. No polymerization of ester 3 could be detected in the presence of TiCl4 in CH2Cl2. The reactivity difference between 2 and 3 in TiCl4-catalyzed Diels-Alder reactions may possibly be attributable to the stabilization of the 3-TiCl4 complex or weakening of Lewis acidity by coordination of the bidentate ester group of 3. The synthesis of all-trans-16,16,16-trifluororetinal (4), which is considered to be an important analogue for the study of retinal-binding protein, was conducted on the basis of these results. Comparison of the absorption maximum (362 nm) of 4 with other trifluororetinal 34 (362 nm) and 35 (382 nm) reported previously suggests the possibility of a large torsion of the conjugated system between the ring and the polyenal side chain in 4.
• Lewis acid-catalysed ene reactions of esters of 2-trifluoromethylpropenoic acid
  作者：Yuji Hanzawa、Makoto Suzuki、Takeshi Sekine、Tetsu Murayama、Takeo Taguchi

  DOI：10.1039/c39910000721

  日期：——

  In Lewis acid-catalysed ene reactions of esters (1 and 2) of 2-trifluoromethylpropenoic acid, the high reactivity of 1 and 2 and preparation of an optically active trifluoromethylated tertiary carbon (S-configuration, >80% diastereoisomeric excess) by TiCl4-catalysed ene reactions of 2 are reported.

  在酯（路易斯酸催化的烯反应1和2的2-trifluoromethylpropenoic酸，的高反应性）1个2以及制备光学活性的三氟甲基化的叔碳的（小号通过的TiCl -构型，> 80％非对映体过量）4据报道，催化的烯反应为2。