2-(hydroxy(4-nitrophenyl)methyl)cycloheptanone | 1305197-04-9

• 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)cycloheptanone
• 英文别名: (2R,1'R)-2-[hydroxy-(4-nitrophenyl)-methyl]-cycloheptanone；2-(hydroxy(4-nitrophenyl)methyl)cycloheptan-1-one；(2R,1'R)-2-(hydroxy(4-nitrophenyl)methyl)cycloheptan-1-one；(R)-2-((R)-hydroxy(4-nitrophenyl)methyl)cycloheptanone；(2R)-2-[(R)-hydroxy-(4-nitrophenyl)methyl]cycloheptan-1-one
• CAS: 1305197-04-9
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: XIYPQAZIVNVHJP-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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 、 环庚酮 在 2,4-二硝基酚 、 C₁₃H₁₈N₄O₂ 、 sodium chloride 作用下， 以 水 为溶剂， 反应 24.0h， 生成 2-(hydroxy(4-nitrophenyl)methyl)cycloheptanone 、 2-(hydroxy(4-nitrophenyl)methyl)cycloheptanone
  参考文献：
  名称：

  Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2011.06.017

文献信息

• Asymmetric Aldol Reaction Catalyzed by the Anion of an Ionic Liquid
  作者：Vincent Gauchot、Andreea R. Schmitzer

  DOI：10.1021/jo300737u

  日期：2012.6.1

  its applications as a catalyst for the asymmetric aldol reaction. By performing the aldol reaction in [Bmim]NTf2 as a solvent, we report excellent isolated yields of the aldol product (up to 99%), as well as modest to excellent selectivities (dr superior to 99:1. ee up to 89%). Mechanistic insights and the origins of the selectivity of the aldol reaction are discussed on the basis of the results obtained

  本文中，我们报道了衍生自反式-1-羟基脯氨酸的手性咪唑盐的合成及其作为不对称羟醛反应的催化剂的应用。通过在[Bmim] NTf 2中作为溶剂进行羟醛反应，我们报告了羟醛产物的优良分离产率（高达99％），以及中等至优异的选择性（dr优于99：1 ee高达89） ％）。基于两种具有不同氢键电势的​​催化咪唑盐获得的结果，讨论了机械学见解和醛醇缩合反应选择性的起源。
• 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
  作者：Sergio Rossi、Tiziana Benincori、Laura Maria Raimondi、Maurizio Benaglia

  DOI：10.1055/s-0039-1690777

  日期：2020.4

  This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride)

  该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
• 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。
• Highly enantioselective aldol reactions catalyzed by reusable upper rim-functionalized calix[4]arene-based l -proline organocatalyst in aqueous conditions
  作者：Zheng-Yi Li、Yuan Chen、Chong-Qian Zheng、Yue Yin、Liang Wang、Xiao-Qiang Sun

  DOI：10.1016/j.tet.2016.11.052

  日期：2017.1

  l-Proline derivatives have been synthesized and employed for the enantioselective aldol reactions between cyclic ketones and aromatic aldehydes in the presence of water. Good to excellent yields (up to 96%), enantioselectivities (up to 99% ee), as well as diastereoselectivities (up to 99:1 dr) were obtained under the optimal reaction conditions. Detailed experiments clearly showed that the hydrophobic

  合成了一系列上边缘官能化的杯[4]芳烃基的1-脯氨酸衍生物，并将其用于在水存在下环状酮与芳族醛之间的对映选择性羟醛反应。在最佳反应条件下，获得了优良的产率（高达96％），对映选择性（高达99％ee）和非对映选择性（高达99：1 dr）。详细的实验清楚地表明，疏水杯芳烃平台不仅有助于良好的反应性和对映选择性，而且还表现出尺寸选择性催化功能。而且，有机催化剂可以容易地回收并再用于几次运行而对映选择性没有明显损失。
• L-t-Leucine-Catalyzed Direct Asymmetric Aldol Reaction of Cyclic Ketones
  作者：Takuya Kanemitsu、Atsushi Umehara、Michiko Miyazaki、Kazuhiro Nagata、Takashi Itoh

  DOI：10.1002/ejoc.201001413

  日期：2011.2

  L-t-Leucine-catalyzed direct asymmetric aldol reactions are described. In the aldol reaction of p-nitrobenzaldehyde with a cyclic ketone at room temperature, L-t-leucine exhibits catalytic activity resulting in moderate to high diastereo- and enantioselectivity. Use of cycloheptanone or cyclooctanone as a substrate resulted in production of the syn selective product.

  描述了 Lt-亮氨酸催化的直接不对称醛醇反应。在室温下对硝基苯甲醛与环酮的羟醛反应中，Lt-亮氨酸表现出催化活性，导致中等到高的非对映选择性和对映选择性。使用环庚酮或环辛酮作为底物导致产生顺式选择性产物。