2-(hydroxy(4-nitrophenyl)methyl)cyclobutanone

• 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: 2-(hydroxy(4-nitrophenyl)methyl)cyclobutanone
• 英文别名: 2-[hydroxy-(4-nitrophenyl)methyl]cyclobutan-1-one
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: MUGCRBQKEJGGEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  环丁酮 、 对硝基苯甲醛 在 (S)-N-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-6-yl)-prolinamide trifluoroacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.08h， 以10.345%的产率得到
  参考文献：
  名称：

  氨基尿嘧啶的脯氨酰胺，可通过互补模块修饰的有机催化剂

  摘要：

  带有氨基尿嘧啶的脯氨酰胺有机催化剂具有增强的NH酸度，额外的氢键供体以及通过沃森-克里克配对与互补模块自组装的特点。每个模块都会影响反应的选择性，特别是2,6-二氨基吡啶对反应的选择性有益。

  DOI：

  10.1002/ejoc.201800886

文献信息

• Highly efficient primary amine organocatalysts for the direct asymmetric aldol reaction in brine
  作者：Xiao Ma、Chao-Shan Da、Lei Yi、Ya-Ning Jia、Qi-Peng Guo、Li-Ping Che、Feng-Chun Wu、Jun-Rui Wang、Wei-Ping Li

  DOI：10.1016/j.tetasy.2009.05.032

  日期：2009.7

  amine organocatalysts, derived from natural primary amino acids, in combination with 2,4-dinitrophenol (DNP) have proven to be efficient in the presence of brine without further addition of organic solvents. The system formed by 1f and DNP was the most efficient one; it can catalyze the direct aldol reaction with a broad range of ketones and aromatic aldehydes, giving the corresponding aldol products

  由六种衍生自天然伯氨基酸的伯胺有机催化剂与2,4-二硝基苯酚（DNP）组合而成的有机催化系统已证明在盐水存在下无需进一步添加有机溶剂即可有效。由1f和DNP组成的系统是最有效的系统。它可以与广泛的酮和芳族醛催化直接的羟醛反应，以高收率提供相应的羟醛产物，具有高达近乎完美的非对映体和对映体选择性（最高99/1顺/反，对映体> 99％ee）。
• Antibody-catalyzed decarboxylation and aldol reactions using a primary amine molecule as a functionalized small nonprotein component
  作者：Fumihiro Ishikawa、Kouki Uno、Masao Nishikawa、Takeshi Tsumuraya、Ikuo Fujii

  DOI：10.1016/j.bmc.2013.09.015

  日期：2013.11

  Catalytic antibody 27C1 bears binding sites for both a substrate-and a functionalized small nonprotein component in the active site. We investigated the possibility of exploiting imine and enamine intermediates using a primary amine molecule into the active site of antibody 27C1. The antibody catalyzed beta-keto acid decarboxylation with a rate enhancement (k(cat)/K-m/k(uncat)) of 140,000, as well as highly regioselective cross-aldol reactions of ketones and p-nitrobenzaldehyde. These studies provide new strategies for the generation of catalytic antibodies possessing binding sites for functionalized components. (C) 2013 Elsevier Ltd. All rights reserved.
• Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine
  作者：Hua Tian、Jun-long Gao、Hao Xu、Liang-Yu Zheng、Wen-Bo Huang、Qing-Wen Liu、Suo-Qin Zhang

  DOI：10.1016/j.tetasy.2011.06.017

  日期：2011.5

  Simple N-proline-based dipeptides with two N-H groups in combination with 2,4-dinitrophenol (DNP) catalyze the direct asymmetric aldol reactions of aldehydes with a broad range of ketones to furnish the corresponding aldol products in high yields (up to 99%) and with high enantioselectivities (up to 97%) and diastereoselectivities (up to > 99:1, anti/syn) at room temperature and in brine. (C) 2011 Elsevier Ltd. All rights reserved.
• Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules
  作者：Karen M. Ruíz-Pérez、Beatriz Quiroz-García、Marcos Hernández-Rodríguez

  DOI：10.1002/ejoc.201800886

  日期：2018.11.8

  Prolinamide organocatalysts with aminouracils have the features of enhanced NH acidity, an additional hydrogen‐bond donor and the self‐assembly with complementary modules by Watson–Crick pairing. Each module affects the selectivity of the reaction and particularly 2,6‐diaminopyridine is beneficial to the selectivity in the reaction.

  带有氨基尿嘧啶的脯氨酰胺有机催化剂具有增强的NH酸度，额外的氢键供体以及通过沃森-克里克配对与互补模块自组装的特点。每个模块都会影响反应的选择性，特别是2,6-二氨基吡啶对反应的选择性有益。