Methyl (2E,4E)-3-methyl-5-(2,6-dimethyl-6-(trifluoromethyl)-1-cyclohexen-1-yl)-2,4-pentadienoate | 123522-12-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl (2E,4E)-3-methyl-5-(2,6-dimethyl-6-(trifluoromethyl)-1-cyclohexen-1-yl)-2,4-pentadienoate
• 英文别名: methyl (2E,4E)-5-[2,6-dimethyl-6-(trifluoromethyl)cyclohexen-1-yl]-3-methylpenta-2,4-dienoate
• CAS: 123522-12-3
• 化学式: C₁₆H₂₁F₃O₂
• 分子量: 302.337
• InChiKey: RUIPHSFGKBSUFF-ZDVGBALWSA-N

物化性质

• 沸点：
  331.0±37.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  Methyl (2E,4E)-3-methyl-5-(2,6-dimethyl-6-(trifluoromethyl)-1-cyclohexen-1-yl)-2,4-pentadienoate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 生成 (2E,4E)-3-Methyl-5-(2,6-dimethyl-6-(trifluoromethyl)-1-cyclohexen-1-yl)-2,4-pentadienal
  参考文献：
  名称：

  Trifluoromethyl group on quarternary carbon; synthesis of 16,16,16-trifluororetinal

  摘要：

  DOI：

  10.1016/s0040-4039(00)95257-2
• 作为产物：
  描述：

  2,2,2-Trifluoroethyl 1-(trifluoromethyl)-3-methyl-4-oxo-2-cyclohexene-1-carboxylate 在 manganese(IV) oxide 、 正丁基锂 、 Celite 、 甲基三苯氧基碘磷 、 三正丁基氢锡 、 potassium hydride 、 dipyridine chromium trioxide 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 Methyl (2E,4E)-3-methyl-5-(2,6-dimethyl-6-(trifluoromethyl)-1-cyclohexen-1-yl)-2,4-pentadienoate
  参考文献：
  名称：

  Trifluoromethyl group on quarternary carbon; synthesis of 16,16,16-trifluororetinal

  摘要：

  DOI：

  10.1016/s0040-4039(00)95257-2

文献信息

• Trifluoromethyl group on quarternary carbon; synthesis of 16,16,16-trifluororetinal
  作者：Yuji Hanzawa、Makoto Suzuki、Yoshiro Kobayashi

  DOI：10.1016/s0040-4039(00)95257-2

  日期：1989.1
• HANZAWA, YUJI;SUZUKI, MAKOTO;KOBAYASHI, YOSHIRO;TAGUCHI, TAKEO;IITAKA, YO+, J. ORG. CHEM., 56,(1991) N, C. 1718-1725
  作者：HANZAWA, YUJI、SUZUKI, MAKOTO、KOBAYASHI, YOSHIRO、TAGUCHI, TAKEO、IITAKA, YO+

  DOI：——

  日期：——
• HANZAWA, YUJI;SUZUKI, MAKOTO;KOBAYASHI, YOSHIRO, TETRAHEDRON LETT., 30,(1989) N 5, C. 571-574
  作者：HANZAWA, YUJI、SUZUKI, MAKOTO、KOBAYASHI, YOSHIRO

  DOI：——

  日期：——
• 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.