(R)-3-(1-(naphthalen-1-yl)-2-nitroethyl)pentane-2,4-dione | 189952-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-3-(1-(naphthalen-1-yl)-2-nitroethyl)pentane-2,4-dione
• 英文别名: 3-[(1R)-1-naphthalen-1-yl-2-nitroethyl]pentane-2,4-dione
• CAS: 189952-23-6
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: DITOVBPXHUACNS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  β-(1-naphthyl)nitroethylene 、 乙酰丙酮 在 (2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-(3-((1R,2R)-2-(dimethylamino)cyclohexyl)thioureido)tetrahydro-2H-pyran-3,4,5-triyl triacetate 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以97%的产率得到(R)-3-(1-(naphthalen-1-yl)-2-nitroethyl)pentane-2,4-dione
  参考文献：
  名称：

  糖衍生的双功能硫脲有机催化乙酰丙酮与硝基烯烃的不对称迈克尔加成

  摘要：

  带有糖基支架和叔氨基的双功能手性硫脲有机催化剂被证明是乙酰丙酮与硝基烯烃不对称迈克尔加成的有效有机催化剂。相应的加合物以良好到极好的收率获得，具有极好的对映选择性（高达 96% ee）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800555

文献信息

• Bifunctional Thioureas with α-Trifluoromethyl or Methyl Groups: Comparison of Catalytic Performance in Michael Additions
  作者：Eddy I. Jiménez、Wilmer E. Vallejo Narváez、Carlos A. Román-Chavarría、Josue Vazquez-Chavez、Tomás Rocha-Rinza、Marcos Hernández-Rodríguez

  DOI：10.1021/acs.joc.6b01063

  日期：2016.9.2

  Thioureas are an important scaffold in organocatalysis because of their ability to form hydrogen bonds that activate substrates and fix them in a defined position, which allows a given reaction to occur. Structures that enhance the acidity of the thiourea are usually used to increase the hydrogen-bonding properties, such as 3,5-bis(trifluoromethyl)phenyl and boronate ureas. Herein, we report the synthesis

  硫脲是有机催化中的重要支架，因为它们能够形成氢键，从而激活底物并将其固定在确定的位置，从而使给定的反应发生。通常使用增强硫脲酸度的结构来增加氢键合性能，例如3,5-双（三氟甲基）苯基和硼酸酯脲。本文中，我们报道了具有手性部分的双功能硫脲的合成，该手性部分包括三氟甲基或甲基。他们在代表性的迈克尔加成反应中的催化性能用于比较甲基上氟化的电子效应。观察到的关于产量和ee值的差异不能仅归因于不同的空间环境；理论结果表明在相应的过渡态内有明显的相互作用。计算得出的过渡态表明，氟化催化剂具有更强的N–H···O和C–H···F氢键，而非氟化体系则具有C–H···π接触。这些结果表明，各种氢键相互作用对于确定硫脲有机催化的产率和选择性很重要。这些细节可以在催化剂设计中进一步利用。
• Doubly stereocontrolled asymmetric Michael addition of acetylacetone to nitroolefins promoted by an isosteviol-derived bifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Li-juan Huo、Xiang Gao、Jing-chao Tao

  DOI：10.1016/j.tetasy.2012.03.020

  日期：2012.4

  A novel class of chiral bifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a tertiary amino group was designed and prepared. The thioureas were proven to be effective for catalyzing the doubly stereocontrolled asymmetric Michael addition between acetylacetone and nitroolefins. The corresponding adducts were obtained in high yields (up to 95%) and with good to excellent enantioselectivities

  设计并制备了一类新型的手性双官能硫脲，该手性双官能硫脲带有手性亲脂性拜亚烷骨架和叔氨基。硫脲被证明可有效催化乙酰丙酮和硝基烯烃之间的双立体控制的不对称迈克尔加成反应。相应的加合物以高收率（最高95％）和良好至优异的对映选择性（最高97％）获得。此外，乙酰乙酸叔丁酯与反式-β-硝基苯乙烯的反应也顺利进行，具有良好的对映选择性。
• Ferrocene as a scaffold for effective bifunctional amine–thiourea organocatalysts
  作者：Wei Yao、Ming Chen、Xueying Liu、Ru Jiang、Shengyong Zhang、Weiping Chen

  DOI：10.1039/c4cy00199k

  日期：——

  This work demonstrates that ferrocene could be an excellent scaffold for chiral organocatalysts.

  这项工作表明，二茂铁可以作为手性有机催化剂的优秀支架。
• Azetidine-derived bifunctional organocatalysts for Michael reactions
  作者：Laurence Menguy、François Couty

  DOI：10.1016/j.tetasy.2010.08.003

  日期：2010.10

  2-Cyano azetidines, easily accessible from beta-amino alcohols, are precursors of stereodefined homochiral azetidinic or pyrrolidinic 1,2-diamines. A small library of these original diamines was screened as precatalysts for the enantioselective addition of 1,3-dicarbonyl compounds onto beta-nitro styrenes. An azetidinic diamine derived from (-)-ephedrine and derivatized as a thiourea was found to catalyze the conjugate addition of acetylacetone with good levels of enantioselectivities (up to 84% ee). Interestingly, the absolute configuration of the Michael adduct depends on the nature of the 1,3 dicarbonyl nucleophile (diethyl malonate or acetylacetone), which is indicative of a different mechanism involved in the reaction of these two nucleophiles. (C) 2010 Elsevier Ltd. All rights reserved.