O-[(R)-1-(pentafluorophenyl)-3-oxobutyl] N-(4-bromophenyl)carbamate | 1245927-15-4

• 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: O-[(R)-1-(pentafluorophenyl)-3-oxobutyl] N-(4-bromophenyl)carbamate
• 英文别名: [(1R)-3-oxo-1-(2,3,4,5,6-pentafluorophenyl)butyl] N-(4-bromophenyl)carbamate
• CAS: 1245927-15-4
• 化学式: C₁₇H₁₁BrF₅NO₃
• 分子量: 452.175
• InChiKey: UGZYJGZCIXGXFP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-4-hydroxy-4-(pentafluorophenyl)-butan-2-one 、 4-溴异氰酸苯酯 以 氯仿 为溶剂， 反应 120.0h， 以95%的产率得到O-[(R)-1-(pentafluorophenyl)-3-oxobutyl] N-(4-bromophenyl)carbamate
  参考文献：
  名称：

  Cyclic carbonates as sustainable solvents for proline-catalysed aldol reactions

  摘要：

  Ethylene and propylene carbonates, which can be prepared from epoxides and carbon dioxide, are effective solvents for the proline-catalysed, 100% atom economical, asymmetric aldol reaction between enolisable and non-enolisable carbonyl compounds. The optimal cyclic carbonate to use for a particular aldol reaction along with the need for water as a cosolvent appear to be determined by the polarities of the various components present in the reaction mixture. Both cyclic and acyclic ketones can be used as the enamine precursor and react best with electron-deficient aldehydes, such as 4-nitrobenzaldehyde and pentafluorobenzaldehyde. Chemical yields of up to 99%, diastereoselectivities of up to 100% and enantioselectivities of up to 99% can be obtained. The relative and/or absolute configuration of three of the aldol products are determined unambiguously by X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.051

文献信息

• Cyclic carbonates as sustainable solvents for proline-catalysed aldol reactions
  作者：William Clegg、Ross W. Harrington、Michael North、Francesca Pizzato、Pedro Villuendas

  DOI：10.1016/j.tetasy.2010.03.051

  日期：2010.5

  Ethylene and propylene carbonates, which can be prepared from epoxides and carbon dioxide, are effective solvents for the proline-catalysed, 100% atom economical, asymmetric aldol reaction between enolisable and non-enolisable carbonyl compounds. The optimal cyclic carbonate to use for a particular aldol reaction along with the need for water as a cosolvent appear to be determined by the polarities of the various components present in the reaction mixture. Both cyclic and acyclic ketones can be used as the enamine precursor and react best with electron-deficient aldehydes, such as 4-nitrobenzaldehyde and pentafluorobenzaldehyde. Chemical yields of up to 99%, diastereoselectivities of up to 100% and enantioselectivities of up to 99% can be obtained. The relative and/or absolute configuration of three of the aldol products are determined unambiguously by X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.