2-[hydroxy-(4-nitrophenyl)methyl]cyclopentanone

• 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]cyclopentanone
• 英文别名: (S)-2-((S)-hydroxy(3-nitrophenyl)methyl)cyclopentanone；(2S)-2-((S)-hydroxy(3-nitrophenyl)methyl)cyclopentan-1-one；(2S)-2-[(S)-hydroxy(3-nitrophenyl)methyl]cyclopentanone；(2S,1'S)-2-[hydroxy-(3-nitrophenyl)-methyl]-cyclopentanone；(2S,10S)-2-[hydroxy(3-nitrophenyl)methyl]cyclopentan-1-one；2-(hydroxyl-(3-nitrophenyl)methyl)-cyclopentan-1-one；2-(hydroxy(3-nitrophenyl)methyl)cyclopentan-1-one；2-[hydroxy(3-nitrophenyl)methyl]cyclopentanone；(2S)-2-[(S)-hydroxy-(3-nitrophenyl)methyl]cyclopentan-1-one
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: NARLCEZIFIKPSE-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  2-[hydroxy-(4-nitrophenyl)methyl]cyclopentanone 在 NH₂-Val-(D-Pro)-Gly-Leu-OH 、 苯甲酸 作用下， 以 乙醇 为溶剂， 反应 300.0h， 以10%的产率得到2-[hydroxy-(4-nitrophenyl)methyl]cyclopentanone
  参考文献：
  名称：

  Highly enantioselective biomimetic intramolecular dehydration: kinetic resolution of β-hydroxy ketones catalyzed by β-turn tetrapeptides

  摘要：

  Racemic beta-hydroxy ketones were kinetically resoluted into the enantiopure isomers and (E)-alpha,beta-unsaturated ketones using catalytic asymmetric intramolecular dehydration for the first time. Synthetic tetrapeptides were used to imitate fatty acid dehydratases to efficiently discriminate racemic beta-hydroxy ketones, enantioselectively catalyze the intramolecular dehydration, and result in highly enantioenriched beta-hydroxy and (E)-alpha,beta-unsaturated ketones in the environmentally benign process. Mechanistically, the high discrimination of the racemic substrates and successive enantioselective dehydration are highly dependent on the cooperative catalysis of the NH2 and COOH groups of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.087
• 作为产物：
  描述：

  间硝基苯甲醛 、 环戊酮 在 1,4-di(trans-4-tert-butyldiphenylsiloxy-L-prolinamide)butane 、 水 作用下， 反应 24.0h， 以96%的产率得到
  参考文献：
  名称：

  Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

  摘要：

  本研究介绍了五种新型 C2 对称有机催化剂的合成，这些催化剂可在不使用添加剂的情况下，以较低的催化剂负载量（1 摩尔%）促进水上不对称醛醇反应。每种催化剂都由两个二烯丙基酰胺单元组成，并由一个对称的烷基桥基连接，从而可以系统地调节催化位点的邻近性。通常情况下，本手稿中催化位点距离较近的催化剂在转化率（高达 >99%）、非对映异构体比率（4/96，同/反）和对映异构体过量（高达 97%）方面的反应效果最好。这种效果归因于在水包油界面的氢键作用下形成的手性口袋。

  DOI：

  10.1039/c3ob27250h

文献信息

• Highly Diastereo- and Enantioselective Aldol Reactions in Common Organic Solvents Using<i>N</i>-Arylprolinamides as Organocatalysts with Enhanced Acidity
  作者：Jarugu Narasimha Moorthy、Satyajit Saha

  DOI：10.1002/ejoc.200800960

  日期：2008.12.29

  steric crowding has been synthesized and its catalytic activity explored for enantioselective aldol reactions. In DMF containing 10 mol-% of TFA, all arylamides are found to catalyze the reaction between cyclohexanone and a variety of electrophilic aldehydes leading to aldols in excess of 90 % yield and >95 % enantioselectivity. The perfluorophenyl catalyst 8 is found to perform best with a broad substrate

  已经合成了一系列具有增加的 NH 酸度和空间拥挤的 N-芳基脯氨酰胺 1-8，并探索了其对对映选择性醛醇反应的催化活性。在含有 10 mol% TFA 的 DMF 中，发现所有芳基酰胺都能催化环己酮和各种亲电子醛之间的反应，导致醛醇的产率超过 90%，对映选择性大于 95%。与所有其他 N-芳基酰胺 1-7 相比，发现全氟苯基催化剂 8 在广泛的底物范围内表现最佳。结果表明，8 确实可以在高度非极性以及极性溶剂（包括盐水）中使用，以提供具有优异非对映选择性和对映选择性的高收率醛醇。对于不含额外立体中心和氢键位点的脯氨酰胺，对 8 观察到的结果是迄今为止报道的最好的结果之一。7 和 8 的分子结构，通过 X 射线晶体学确定并被认为反映了最稳定的构象，揭示了 N-芳环构象的显着差异；在 7 的情况下，芳环表现出与酰胺官能团共面的趋势，而在 8 的情况下，全氟苯环相对于官能团的酰胺平面几乎垂直扭曲。
• New simple and recyclable O-acylation serine derivatives as highly enantioselective catalysts for the large-scale asymmetric direct aldol reactions in the presence of water
  作者：Chuanlong Wu、Xiangkai Fu、Shi Li

  DOI：10.1016/j.tet.2011.03.083

  日期：2011.6

  products in high yields (up to 99%) and enantioselectivities (up to 99% ee). The catalyst 1b can be easily recovered and reused, and without significant decrease of enantioselectivity was observed for five cycles. This novel catalyst can be efficiently used in large-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry

  通过在室温下在三氟乙酸中将丝氨酸与酰氯合理结合，一步合成了新型的O-酰化丝氨酸衍生的有机催化剂。任何步骤均不涉及保护基团或色谱技术，某些组合的丝氨酸表面活性剂有机催化剂可介导酮与一系列芳香醛的直接羟醛反应，从而以高收率（高达99％）和对映选择性提供羟醛产物。 （最高99％ee）。催化剂1b可以容易地回收和再利用，并且在五个循环中未观察到对映选择性的显着降低。这种新催化剂可以有效地用于大规模反应，同时将对映选择性保持在同一水平，这为工业应用提供了很大的可能性。
• Highly efficient and solvent-free direct aldol reaction catalyzed by glucosamine-derived prolinamide
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1016/j.tetasy.2010.06.009

  日期：2010.8

  The catalytic activity of novel sugar-based prolinamides in the aldol reaction between ketones and aryl aldehydes has been examined. The prolinamide 1c was found to be an efficient organocatalyst for the asymmetric aldol reaction under solvent-free conditions. A variety of ketones and aldehydes were used as substrates and the corresponding aldol products were obtained in excellent chemical yields with

  已经研究了新型糖基脯氨酰胺在酮和芳基醛之间的醛醇缩合反应中的催化活性。发现脯氨酰胺1c是在无溶剂条件下不对称醛醇缩合反应的有效有机催化剂。多种酮和醛用作底物，并以优异的化学收率获得了相应的羟醛产物，同时具有很高的抗非对映选择性（高达99：1）和对映选择性（高达> 99％）。
• l-Valine Dipeptide Organocatalysts with Two Amide Units for the Direct Asymmetric Aldol Reaction in Brine
  作者：Wenbo Huang、Hua Tian、Hao Xu、Liangyu Zheng、Qingwen Liu、Suoqin Zhang

  DOI：10.1007/s10562-011-0589-z

  日期：2011.6

  a primary amine group and two amide units have been developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. When 2,4-dinitrophenol (DNP) was used as an acidic additive, the catalyzed reactions of various aldehydes and ketones gave the corresponding aldol products with moderate to high enantioselectivities (up to 95%) and diastereoselectivities

  一系列含有伯胺基团和两个酰胺单元的缬氨酸二肽有机催化剂已被开发并在 4-硝基苯甲醛和环己酮的直接不对称分子间醛醇反应中进行评估。当使用 2,4-二硝基苯酚 (DNP) 作为酸性添加剂时，各种醛和酮的催化反应得到相应的醛醇产物，具有中到高的对映选择性（高达 95%）和非对映选择性（高达 >99/1， anti/syn) 在 3c 存在于盐水中。图形摘要。
• Simple and inexpensive threonine-based organocatalysts as highly active and recoverable catalysts for large-scale asymmetric direct stoichiometric aldol reactions on water
  作者：Chuanlong Wu、Xiaoqin Long、Shi Li、Xiangkai Fu

  DOI：10.1016/j.tetasy.2012.02.023

  日期：2012.3

  direct asymmetric stoichiometric aldol reaction on water by using variable amounts of water. These threonine-based organocatalyst were simple, inexpensive, highly active and could be synthesized on a large-scale. Among them, the threonine-based organocatalyst 1a is applicable to the stoichiometric reactions of a wide range of aromatic and heteroaromatic aldehydes with ketones, with the aldol products

  通过使用可变量的水，筛选了九种O-酰化苏氨酸，其负载量为0.5–5 mol％，可用于在水中直接不对称化学计量的羟醛直接反应。这些基于苏氨酸的有机催化剂简单，廉价，活性高，可以大规模合成。其中，基于苏氨酸的有机催化剂1a适用于多种芳香族和杂芳香族醛与酮的化学计量反应，所制得的醛醇产物的反/合成比高达99：1 ，ee大于99％。苏氨酸基有机催化剂1a可以容易地回收和再利用，并且在六个循环后仅观察到对映选择性的轻微降低。该新的基于苏氨酸的有机催化剂1a可以有效地用于大规模反应，同时将对映选择性保持在相同水平，这为工业应用提供了很大的可能性。