(S)-3-(1,3-dioxolan-2-yl)-1-[2-(2,2,2-trifluoro-1-methoxyethyl)phenyl]propan-1-one | 670247-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(1,3-dioxolan-2-yl)-1-[2-(2,2,2-trifluoro-1-methoxyethyl)phenyl]propan-1-one
• CAS: 670247-26-4
• 化学式: C₁₅H₁₇F₃O₄
• 分子量: 318.293
• InChiKey: HFYXFPZCPVMKTJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(1,3-dioxolan-2-yl)-1-[2-(2,2,2-trifluoro-1-methoxyethyl)phenyl]propan-1-one 在 乙酸铵 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S,S)-1,9-bis-[2-(2,2,2-trifluoro-1-methoxyethyl)phenyl]-5-phenyl-10H-dipyrrin
  参考文献：
  名称：

  Synthesis, Chiroptical Properties, and Solid-State Structure Determination of Two New Chiral Dipyrrin Difluoroboryl Chelates

  摘要：

  Two new types of optically active BODIPY fluorophores bearing chiral phenyl substituents either at the meso-position or at both external alpha-positions have been synthesized. Their chiroptical properties are strongly dependent both on the position of the chiral group and on the protonation of the chromophore. The solid-state structures of one of the difluoroboryl chelates bearing the chiral phenyl substituent at the meso-position (9a) as well as of the corresponding ligand (8a) and its perchlorate have been determined by X-ray diffraction analysis. These are, to the best of our knowledge, the first crystal structures of a dipyrrin free base and of a dipyrrin salt which have been obtained by X-ray diffraction analysis. Hence, for the first time, the helical structure of a protonated dipyrrin chromophore has been proved experimentally.

  DOI：

  10.1021/ja030542r
• 作为产物：
  描述：

  (1S)-1-[2-(1,3-dioxolan-2-yl)phenyl]-2,2,2-trifluoro-1-ethanol 在 吡啶 、 盐酸 、 sodium acetate 、 magnesium 、 pyridinium chlorochromate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (S)-3-(1,3-dioxolan-2-yl)-1-[2-(2,2,2-trifluoro-1-methoxyethyl)phenyl]propan-1-one
  参考文献：
  名称：

  Synthesis, Chiroptical Properties, and Solid-State Structure Determination of Two New Chiral Dipyrrin Difluoroboryl Chelates

  摘要：

  Two new types of optically active BODIPY fluorophores bearing chiral phenyl substituents either at the meso-position or at both external alpha-positions have been synthesized. Their chiroptical properties are strongly dependent both on the position of the chiral group and on the protonation of the chromophore. The solid-state structures of one of the difluoroboryl chelates bearing the chiral phenyl substituent at the meso-position (9a) as well as of the corresponding ligand (8a) and its perchlorate have been determined by X-ray diffraction analysis. These are, to the best of our knowledge, the first crystal structures of a dipyrrin free base and of a dipyrrin salt which have been obtained by X-ray diffraction analysis. Hence, for the first time, the helical structure of a protonated dipyrrin chromophore has been proved experimentally.

  DOI：

  10.1021/ja030542r