(2S,1'R)-2-[1'-hydroxy-1'-(4-nitrophenyl)methyl]-4-tert-butylcyclohexanone | 1187618-63-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,1'R)-2-[1'-hydroxy-1'-(4-nitrophenyl)methyl]-4-tert-butylcyclohexanone
• 英文别名: (2S)-4-tert-butyl-2-[(R)-hydroxy-(4-nitrophenyl)methyl]cyclohexan-1-one
• CAS: 1187618-63-8
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: MJKIGGVYMRBFNA-TUJLOAKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 4-叔丁基环己酮 在 碳酸丙烯酯 、 水 、 L-脯氨酸 作用下， 反应 24.0h， 以58%的产率得到(2S,1'R)-2-[1'-hydroxy-1'-(4-nitrophenyl)methyl]-4-tert-butylcyclohexanone
  参考文献：
  名称：

  A Chiral Solvent Effect in Asymmetric Organocatalysis

  摘要：

  Proline-catalyzed aldol reactions between enolizable ketones and aromatic aldehydes can be carried out in propylene carbonate. When enantiomerically pure propylene carbonate is used, the combination of (R)-proline and (R)-propylene carbonate constitutes a matched pair, while (S)-proline and (R)-propylene carbonate constitutes a mismatched pair.

  DOI：

  10.1021/ol1007313

文献信息

• Amino Acid Catalysed Aldol Reactions in Cyclic Carbonate Solvents
  作者：Michael North、Maria Morcillo、Pedro Villuendas

  DOI：10.1055/s-0030-1260038

  日期：2011.6

  Ethylene and propylene carbonates are shown to be alternative polar aprotic solvents for cross-aldol reactions catalysed by the primary amino acids (S)-phenylalanine and (S)-tryptophan. In contrast to the corresponding proline-catalysed reactions, both enantiomers of these naturally occurring, primary amino acids are available at low cost. The optimal catalyst and solvent combination needs to be determined on a substrate by substrate basis.

  研究表明，乙烯和碳酸丙烯酯是初级氨基酸 (S)-phenylalanine 和 (S)-tryptophan 催化的交醛反应的替代极性无水溶剂。与相应的脯氨酸催化反应不同的是，这些天然存在的初级氨基酸的两种对映体都可以低成本获得。催化剂和溶剂的最佳组合需要根据不同的底物来确定。
• Banerjee, Mainak; Das, Sunirban; Yoon, Minyoung, Journal of the American Chemical Society, 2009, vol. 131, p. 7524 - 7525
  作者：Banerjee, Mainak、Das, Sunirban、Yoon, Minyoung、Choi, Hee Jung、Hyun, Myung Ho、et al.

  DOI：——

  日期：——
• 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.