(R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanol | 1415666-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanol
• 英文别名: 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanol；(1R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2,2,2-trifluoroethan-1-ol；(1R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2,2,2-trifluoroethanol
• CAS: 1415666-70-4
• 化学式: C₁₀H₉F₃O₃
• 分子量: 234.175
• InChiKey: QBFYQMMKZRQMBH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-苯并二恶烷-6-甲醛 在 [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper (I) fluoride 、 N-(3,5-ditrifluoromethylbenzyl)quinidinium bromide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.17h， 生成 (R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanol 、 (S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanol
  参考文献：
  名称：

  Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt

  摘要：

  已经开发了一种针对醛类的通用对映选择性三氟甲基化反应，使用(IPr)CuF和奎宁衍生的四价铵盐作为协同催化剂。因此，广泛的芳香醛被转化为相应的产物，产率高达92%，对映体过剩率（ee）为81%，催化剂用量为2摩尔百分比。显著增强的活性和对映选择性源于活性[(IPr)CuCF3]的初始生成以及其他铜物种的额外配位活化。

  DOI：

  10.1039/c2ob26827b

文献信息

• The enantioselective trifluoromethylation of aromatic aldehydes by quaternary ammonium bromide and (IPr)CuF at low catalyst loading
  作者：Shaoxiang Wu、Jiyi Guo、Muhammad Sohail、Chengyao Cao、Fu-Xue Chen

  DOI：10.1016/j.jfluchem.2013.01.027

  日期：2013.4

  A general catalytic enantioselective trifluoromethylation of aromatic aldehydes using (IPr)CuF and quinidine-derived quaternary ammonium salt as catalysts has been developed. A wide range of aromatic aldehydes are converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. (C) 2013 Elsevier B.V. All rights reserved.
• Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt
  作者：Shaoxiang Wu、Wei Zeng、Qi Wang、Fu-Xue Chen

  DOI：10.1039/c2ob26827b

  日期：——

  A general enantioselective trifluoromethylation of aldehydes has been developed using (IPr)CuF and quinidine-derived quaternary ammonium salt as the cooperative catalyst. Thus, a wide range of aromatic aldehydes have been converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. The greatly enhanced activity and enantioselectivity result from the initiative generation of active [(IPr)CuCF3] as well as additional coordination activation of other copper species.

  已经开发了一种针对醛类的通用对映选择性三氟甲基化反应，使用(IPr)CuF和奎宁衍生的四价铵盐作为协同催化剂。因此，广泛的芳香醛被转化为相应的产物，产率高达92%，对映体过剩率（ee）为81%，催化剂用量为2摩尔百分比。显著增强的活性和对映选择性源于活性[(IPr)CuCF3]的初始生成以及其他铜物种的额外配位活化。