(3S,4S)-3,4-dihydroxy-4-(2-nitrophenyl)butan-2-one | 1160859-92-6

• 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: (3S,4S)-3,4-dihydroxy-4-(2-nitrophenyl)butan-2-one
• 英文别名: (3S,4S)-4-(2-nitrophenyl)-3,4-dihydroxybutan-2-one
• CAS: 1160859-92-6
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: XAPHDBGLNQPKIJ-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟基丙酮 、 邻硝基苯甲醛 在 NH₂-Val-(D-Pro)-Gly-Leu-OH 、 S-1,1'-联-2-萘酚 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 (3S,4S)-3,4-dihydroxy-4-(2-nitrophenyl)butan-2-one 、 4-(2-nitrophenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  N-伯胺-末端β-Turn四肽作为有机催化剂用于高度对映选择性的醛醇缩合反应

  摘要：

  设计并合成了四肽，该四肽包含一个终止的伯胺和构象受限的d -Pro-Gly或d -Pro-Aib（2-氨基异丁酸）链段作为强β-转核元素，并通过N-模块二肽与溶液中的C模块二肽。它们首先被用于催化羟醛反应，并被发现是有效的转化催化剂。四肽Val- d -Pro-Gly-Leu-OH（1g）是最佳的有机催化剂。结果表明，在密集的β转角构象，通过CD和NOESY光谱表明，促成了（ř）-丙酮中的丙酮反应具有较高的对映选择性，而急剧变化的构象应有助于1,2-二氯乙烷（DCE）中反应的低对映选择性和（S）产物。羟基丙酮反应中的不对称诱导不受溶剂的影响，在MeCN中添加1克添加剂（S）-BINOL可达到主要的反产物。

  DOI：

  10.1021/jo9005766

文献信息

• Direct asymmetric aldol condensation catalyzed by aziridine semicarbazide zinc(II) complexes
  作者：Adam M. Pieczonka、Stanisław Leśniak、Michał Rachwalski

  DOI：10.1016/j.tetlet.2014.02.131

  日期：2014.4

  Previously obtained semicarbazides derived from N-triphenylmethyl-aziridine-2-carbohydrazide were explored as ligands in Zn(II) catalyzed diastereo- and enantioselective direct aldol reactions. Complexes of aziridine-semicarbazides with Zn(II) were efficient catalysts in reactions of acetone and hydroxyacetone with NO2-substituted aromatic aldehydes in the presence of water.

  在锌（II）催化的非对映和对映选择性直接醛醇缩合反应中，探索了从N-三苯基甲基-氮丙啶-2-碳酰肼衍生的先前获得的氨基脲作为配体。氮丙啶-氨基脲与Zn（II）的配合物是丙酮和羟基丙酮与NO 2取代的芳香醛在水存在下反应的有效催化剂。
• Additive-controlled regioselective direct asymmetric aldol reaction of hydroxyacetone and aldehyde
  作者：Ling-yan Liu、Bing Wang、Yunna Zhu、Wei-xing Chang、Jing Li

  DOI：10.1016/j.tetasy.2013.03.018

  日期：2013.5

  developed for the direct asymmetric aldol reaction of hydroxyacetone and various aldehydes with moderate to high yields and high enantioselectivities. More importantly, this regioselective reaction could be easily regulated by changing the additives in the presence of the same organocatalyst 1b, to afford the normal 1,2-diol adducts and the disfavoured 1,4-diol products, respectively, in a highly regioselective

  已经开发了由1-脯氨酸和1-缬氨酸制备的结构简单的二肽衍生物1b，用于羟丙酮和各种醛的直接不对称醛醇缩合反应，具有中等至高收率和高对映选择性。更重要的是，可以通过在相同的有机催化剂1b的存在下改变添加剂来轻松地调节区域选择性反应，从而以高度区域选择性的方式分别提供正构1,2-二醇加合物和不利的1,4-二醇产物。还提出了可能的反应机理。
• Simple and practical direct asymmetric aldol reaction of hydroxyacetone catalyzed by 9-amino Cinchona alkaloid tartrates
  作者：Paweł Czarnecki、Agnieszka Plutecka、Jacek Gawroński、Karol Kacprzak

  DOI：10.1039/c1gc15064b

  日期：——

  procedure for the direct aldol reaction of unprotected acetol and activated aromatic aldehydes catalyzed by 9-amino-9-epi-Cinchona ditartrates is presented. The protocol presented avoids the use of problematic solvents and toxic reagents as well as chromatographic purification of the products – instead a simple extraction has been applied for the isolation of pure aldols from the reaction mixture. This

  一种新的有机催化方法，用于未保护基的直接羟醛反应 丙酮醇 和活化的芳烃 醛类 由...催化 9-氨基-9-外延-金鸡纳介绍了酒石酸氢盐。提出的协议避免了使用有问题的溶剂 和有毒试剂以及色谱 纯化 产品–而不是简单的 萃取已用于从反应混合物中分离纯羟醛。这个催化该系统专门为线性羟醛提供定量的收率，并具有高达90％ee的良好的顺-非对映选择性和对映选择性。通过单一且可靠的方法，可以轻松完成对映体过量的顺式对映体的进一步纯化，最高可达到ee的99％结晶。指某东西的用途辛可宁 或者 奎宁-衍生的 催化剂允许获得其绝对构型由决定的顺式醇的两个对映体的对映体X射线衍射。使用廉价和可再生化学品的操作方便且可扩展的有机催化程序–两者丙酮醇 和 催化剂，提供了一种可持续的绿色方式来合成许多α-酮-合成-二醇。
• Simple, inexpensive, and facile l-prolinamide used as a recyclable organocatalyst for highly efficient large-scale asymmetric direct aldol reactions
  作者：Jiangwei Xu、Xiangkai Fu、Chuanlong Wu、Xiaoyan Hu

  DOI：10.1016/j.tetasy.2011.05.008

  日期：2011.4

  In order to discover a simple, inexpensive, and efficient route to obtain highly enantiomerically enriched anti-aldol products for applications in industry, a series of prolinamides 1-5 with different carbocyclic rings have been synthesized from achiral cycloalkylamine, and prolinamides 6-9 have been synthesized from aniline with different substituents. The organocatalysts obtained catalyzed the asymmetric aldol reaction and showed that no matter carbocyclic rings or aromatic rings were found to play a significant role in the formation of the aldol products. Moreover, the prolinamide 6 exhibited efficient catalytic activity in the asymmetric aldol reaction only with 5 mol % catalyst loading and 4 equiv of ketone, and afforded aldol products in high diastereoselectivity (up to anti/syn 99:1) and enantioselectivity (99%) and significantly enhanced the reaction yield (99%). These results were much better than L-proline-3-nitroanilide which had the strongest electron-withdrawing group on the aromatic ring. Furthermore, catalyst 6 can be easily recovered and reused, without a significant decrease of enantioselectivity after five cycles. This inexpensive, simple, and recyclable 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. (C) 2011 Elsevier Ltd. All rights reserved.