1-hydroxy-2-methyl-1-(4-nitrophenyl)pentan-3-one

• 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: 1-hydroxy-2-methyl-1-(4-nitrophenyl)pentan-3-one
• 英文别名: (1S,2S)-1-hydroxy-2-methyl-1-(4-nitrophenyl)pentan-3-one
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: OFSNTJXABKDNRR-PELKAZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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 、 3-戊酮 在 (1'R,2'R)-6-(2'-aminocyclohexyl)-6,7-dihydro-5H-dibenzo[c,e]azepine triflate 、 间硝基苯甲酸 作用下， 反应 30.0h， 生成 1-hydroxy-2-methyl-1-(4-nitrophenyl)pentan-3-one 、 1-hydroxy-2-methyl-1-(4-nitrophenyl)pentan-3-one
  参考文献：
  名称：

  使用对苯二氮杂[ c，e ]氮杂有机催化剂的高度对映体选择性羟醛反应

  摘要：

  描述了具有对位二苯并[ c，e ] a庚环的手性伯叔二胺盐的四步合成。结果表明，这种盐的3.5–5 mol％能够促进环己酮与一系列芳香醛之间的高度对映选择性的交叉羟醛反应。在所有情况下，羟醛缩合反应继续进行高非对映选择性的反-aldol产品。还描述了涉及其他环状酮和非环状酮的交叉醇醛缩合反应的结果。所有涉及环状酮的例子都会导致对抗羟醛产物的选择性，而发现非环状酮有利于合成-aldol产品。还讨论了手性伯叔二胺盐在醛醇缩合反应催化中的作用。

  DOI：

  10.1016/j.tet.2011.09.101

文献信息

• Direct Asymmetric Aldol Reaction Catalyzed by C2-Symmetrical Chiral Primary Amine Organocatalysts
  作者：Gong-Jian Zhu、Chao-Shan Da、Ya-Ning Jia、Xiao Ma、Lei Yi

  DOI：10.2174/157017810790533904

  日期：2010.1.1

  C-2-symmetrical chiral primary amines were synthesized from chiral BINOL and diamines. Then their catalytic activities in the asymmetric aldol reactions were evaluated, and the result indicated that 1c was the optimal organocatalyst. The reaction of a variety of aromatic aldehydes with aliphatic ketones, catalyzed by 20 mol % 1c in the addition of benzoic acid in carbon tetrachloride, afforded the aldol products

  从手性 BINOL 和二胺合成了三种新型 C-2 对称手性伯胺。然后评估了它们在不对称醛醇反应中的催化活性，结果表明1c是最佳的有机催化剂。在四氯化碳中加入苯甲酸，在 20 mol % 1c 的催化下，多种芳香醛与脂肪族酮反应得到高产率（高达 92%）和良好的对映选择性（高达 71%）的醛醇产物.
• The application of a structurally simple, recyclable, and large-scale l-prolinamide catalyst for asymmetric aldol reactions
  作者：Zhi Guan、Yuan Luo、Bao-Qiang Zhang、Krystal Heinen、Da-Cheng Yang、Yan-Hong He

  DOI：10.1016/j.tetasy.2014.04.009

  日期：2014.5

  With heterocyclic ketones or cyclohexanone, the aldol reactions gave products in high yields and with respectable enantioselectivities (87–99% ee) and diastereoselectivities (up to >99:1 anti/syn). The catalyst could be recycled and reused up to seven times resulting in good yields and with good selectivities. This catalyst is also efficient in large-scale reactions with the enantioselectivities remaining

  一个高效，双功能催化剂脯氨酰胺，其由手性脯氨酸和的反式-cyclohexanediamine部分，准备和各种酮类和醛类的直接不对称羟醛缩合反应进行评价。该催化剂对含氧，硫或氮的杂环酮显示出令人印象深刻的催化活性，但尚未充分探索。基板范围还覆盖环状和无环酮。与杂环酮或环己酮，醛醇缩合反应，得到的产品在高收率和对映选择性尊敬（87-99％ee）和非对映选择性（高达> 99：1反/顺）。该催化剂可再循环和再利用起来，导致良好的收益率七次，具有良好的选择性。该催化剂也与保持在相同的水平在实验规模的反应对映选择性的大规模反应高效。
• A Simple Primary−Tertiary Diamine−Brønsted Acid Catalyst for Asymmetric Direct Aldol Reactions of Linear Aliphatic Ketones
  作者：Sanzhong Luo、Hui Xu、Jiuyuan Li、Long Zhang、Jin-Pei Cheng

  DOI：10.1021/ja069372j

  日期：2007.3.1

  regio- and diastereoselectivity and enantioselectivity under ambient temperature. Significantly, the reactions accommodate the synthetically important but challenging substrates, such as linear aliphatic ketones, with high regioselectivity and unprecedented syn diastereoselectivity. These results are in sharp contrast with the secondary amine mediated similar reactions wherein anti diastereoselectivity

  与已充分探索的带有仲胺的烯胺催化相比，开发高效的基于烯胺的伯胺催化剂直到最近仍然是一个难以捉摸的目标。我们在本文中提出了一种简单的手性伯-叔二胺 1d 与 TfOH 结合用作有效的基于烯胺的伯胺催化剂。1d-TfOH催化体系可以有效催化不对称直接醛醇反应，底物范围广，在环境温度下具有高区域选择性和非对映选择性以及对映选择性。值得注意的是，这些反应适应了合成上重要但具有挑战性的底物，例如线性脂肪族酮，具有高区域选择性和前所未有的顺式非对映选择性。
• Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by l-tryptophan in the presence of water
  作者：Zhaoqin Jiang、Hui Yang、Xiao Han、Jie Luo、Ming Wah Wong、Yixin Lu

  DOI：10.1039/b921460g

  日期：——

  Primary amino acids and their derivatives were investigated as catalysts for the direct asymmetric aldol reactions between ketones and aldehydes in the presence of water, and L-tryptophan was shown to be the best catalyst. Solvent effects, substrate scope and the influence of water on the reactions were investigated. Quantum chemical calculations were performed to understand the origin of the observed

  研究了伯氨基酸及其衍生物作为在水存在下酮与醛之间直接不对称醛醇缩合反应的催化剂，L-色氨酸是最好的催化剂。研究了溶剂效应，底物范围和水对反应的影响。进行量子化学计算以了解观察到的立体选择性的起源。
• Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts
  作者：Debarshi Sinha、Tanmay Mandal、Sanjib Gogoi、Joshua J. Goldman、John Cong-gui Zhao

  DOI：10.1002/cjoc.201200639

  日期：2012.9.27

  are amino acids and cinchona alkaloid derivatives, leads to the direct formation of the desired organocatalysts without any synthesis. These modularly designed organocatalysts (MDOs) may be used for catalyzed asymmetric aldol reaction. Depending on structure of the aldehyde substrates, the corresponding aldol products may be obtained in mediocre to excellent ee values (up to 92% ee) with moderate diastereoselectivities

  氨基酸和金鸡纳生物碱衍生物等预催化剂模块的自组装可直接形成所需的有机催化剂，而无需任何合成。这些模块化设计的有机催化剂（MDO）可用于催化不对称的羟醛反应。取决于醛底物的结构，可以以中等的非对映选择性（高达79:21 dr）以中等至优异的ee值（高达92％ee）获得相应的羟醛产物。