(E)-3-(2,4-bis-trifluoromethylphenyl)propenal | 262268-46-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(2,4-bis-trifluoromethylphenyl)propenal
• 英文别名: (E)-3-[2,4-bis(trifluoromethyl)phenyl]prop-2-enal
• CAS: 262268-46-2
• 化学式: C₁₁H₆F₆O
• 分子量: 268.158
• InChiKey: PCDGGGOFKWXZOU-OWOJBTEDSA-N

物化性质

• 沸点：
  226.0±35.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,4-bis-trifluoromethylphenyl)propenal 在 sodium hydride 作用下， 反应 15.0h， 生成
  参考文献：
  名称：

  Trifluoromethyl Groups in Crystal Design of 1,4-Diphenyl-1,3-butadienes for Topochemical [2 + 2] Photodimerization

  摘要：

  UV irradiation of the powdered crystalline sample of each of three (EE)-1,4-di(trifluoromethyl-substituted)phenyl-1,3-butadienes (1-3) was found to yield a single [2 + 2] cycloaddition product in the solid state. Moreover, upon irradiation, the crystalline samples of two (EE)-1,4-di(trifluoromethyl- and fluorine-substituted)phenyl-1,3-butadienes (4, 5) undergo a similar conversion to afford a [2 + 2] cycloaddition product, respectively. Our observations suggest that trifluoromethyl groups can be used to direct 1,4-diphenyl-1,3-butadiene molecules to form a parallel, offset-stacked orientation suitable for topochemical [2 + 2] cycloaddition.

  DOI：

  10.1021/ol0475111
• 作为产物：
  描述：

  甲酰甲撑基三苯基磷 、 2,4-双(三氟甲基)苯甲醛 生成 (E)-3-(2,4-bis-trifluoromethylphenyl)propenal
  参考文献：
  名称：

  Trifluoromethyl Groups in Crystal Design of 1,4-Diphenyl-1,3-butadienes for Topochemical [2 + 2] Photodimerization

  摘要：

  UV irradiation of the powdered crystalline sample of each of three (EE)-1,4-di(trifluoromethyl-substituted)phenyl-1,3-butadienes (1-3) was found to yield a single [2 + 2] cycloaddition product in the solid state. Moreover, upon irradiation, the crystalline samples of two (EE)-1,4-di(trifluoromethyl- and fluorine-substituted)phenyl-1,3-butadienes (4, 5) undergo a similar conversion to afford a [2 + 2] cycloaddition product, respectively. Our observations suggest that trifluoromethyl groups can be used to direct 1,4-diphenyl-1,3-butadiene molecules to form a parallel, offset-stacked orientation suitable for topochemical [2 + 2] cycloaddition.

  DOI：

  10.1021/ol0475111

文献信息

• Phenyl β-Methoxyacrylates:  A New Antimalarial Pharmacophore
  作者：Jawad Alzeer、Jacques Chollet、Ingrid Heinze-Krauss、Christian Hubschwerlen、Hugues Matile、Robert G. Ridley

  DOI：10.1021/jm990002y

  日期：2000.2.1

  Phenyl beta-methoxyacrylates, linked to an aromatic ring via an olefinic bridge, have been identified as novel, potentially inexpensive, antimalarial agents. The compounds are believed to exert their activity by inhibition of mitochondrial electron transport at the cytochrome bc(1) complex. A series of compounds have been synthesized to define structure-activity relationships affecting antimalarial activity. It was found that the beta-methoxyacrylate was required ortho to the linker and the optimal bridge was (E,E)-butadiene, Compounds in which the second aromatic ring was ortho-substituted or ortho,para-disubstituted gave optimal potency. Several compounds were identified with potency that is superior to that of chloroquine both in culture and in a murine malaria model.