(1S)-1-[2-(1,3-dioxolan-2-yl)phenyl]-2,2,2-trifluoroethyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate | 670247-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S)-1-[2-(1,3-dioxolan-2-yl)phenyl]-2,2,2-trifluoroethyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 670247-20-8
• 化学式: C₂₁H₂₃F₃O₆
• 分子量: 428.405
• InChiKey: BCJNLGFTYWHENP-PNHOKKKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S)-1-[2-(1,3-dioxolan-2-yl)phenyl]-2,2,2-trifluoroethyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 在 盐酸 、 sodium hydroxide 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 15.0h， 生成 dibenzyl (S)-5-{2-[(2,2,2-trifluoro-1-methoxyethyl)phenyl]}-1,2,6,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-3,5-dicarboxylate
  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：

  1-[2-(1,3-dioxolan-2-yl)phenyl]-2,2,2-trifluoro-1-ethanone 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (1S)-1-[2-(1,3-dioxolan-2-yl)phenyl]-2,2,2-trifluoroethyl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  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