2-acetyl-2-(2-nitro-1-phenylethyl)cyclopentan-1-one | 834917-49-6

• 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: 2-acetyl-2-(2-nitro-1-phenylethyl)cyclopentan-1-one
• 英文别名: (2S)-2-Acetyl-2-[(1S)-2-nitro-1-phenylethyl]cyclopentan-1-one；(2S)-2-acetyl-2-[(1S)-2-nitro-1-phenylethyl]cyclopentan-1-one
• CAS: 834917-49-6
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: GQBWRJIXLLOVME-DZGCQCFKSA-N

物化性质

• 熔点：
  107-109 °C(Solv: methanol (67-56-1))
• 沸点：
  444.3±35.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  2-乙酰基环戊酮 、 β-硝基苯乙烯 在 N-[（1R，2R）-2-（二甲基氨基）环己基]-N''-[（1R，2S）-2-羟基-1,2-二苯乙基]硫脲 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以96%的产率得到2-acetyl-2-(2-nitro-1-phenylethyl)cyclopentan-1-one
  参考文献：
  名称：

  带有多个氢键供体的微调有机催化剂，用于通过迈克尔反应构建相邻的四级和三级立体中心。

  摘要：

  DOI：

  10.1002/chem.200801420

文献信息

• Novel chiral hydrogen bond donor catalysts based on a 4,5-diaminoxanthene scaffold: application to enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes
  作者：Tetsuhiro Nemoto、Kazumichi Obuchi、Shinji Tamura、Takashi Fukuyama、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2010.12.067

  日期：2011.3

  Novel chiral hydrogen bond donor catalysts based on a 4,5-diamino-9,9′-dimethylxanthene skeleton were designed and synthesized. Among the phenylurea-amide hybrid molecules prepared from various natural/unnatural chiral amino acids, the phenylalanine-derived catalyst, and the proline-derived catalyst were successfully applied to enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes

  设计并合成了一种基于4,5-二氨基-9,9'-二甲基x吨骨架的新型手性氢键供体催化剂。在由各种天然/非天然手性氨基酸制备的苯基脲-酰胺杂化分子中，苯丙氨酸衍生的催化剂和脯氨酸衍生的催化剂成功地用于将1，3-二羰基化合物对硝基烯烃的对映选择性共轭加成。使用2-乙酰基环戊酮和2-甲氧基羰基环戊酮作为前手性亲核试剂，向β-芳基硝基链烯的不对称共轭加成反应具有良好的非对映选择性，从而提供了具有全碳四元立体中心的相应产物，收率高达95％ee。
• Ephedrine- and Pseudoephedrine-Derived Thioureas in Asymmetric Michael Additions of Keto Esters and Diketones to Nitroalkenes
  作者：Carsten Bolm、Angelika Flock、Anke Krebs

  DOI：10.1055/s-0029-1219582

  日期：2010.5

  Ephedrine-derived bifunctional thioureas have been synthesized and applied as organocatalysts in Michael additions of 1,3-dicarbonyl compounds to nitroalkenes.

  麻黄碱衍生的双功能硫脲已被合成并用作有机催化剂，用于 1,3-二羰基化合物与硝基烯烃的迈克尔加成反应。
• Recyclable Chiral Bifunctional Thioureas Derived from [60]Fullerene and Their Use as Highly Efficient Organocatalysts for the Asymmetric Nitro-Michael Reaction
  作者：José M. Andrés、Miguel González、Alicia Maestro、Daniel Naharro、Rafael Pedrosa

  DOI：10.1002/ejoc.201601640

  日期：2017.5.18

  Three novel fullerothioureas derived from natural valine, phenylalanine, and tert-leucine have been prepared by Prato's reaction of [60]fullerene and the corresponding aldehydes. These hybrids have been used as organocatalysts in a typical stereoselective nitro-Michael addition reaction under homogeneous and neat conditions. The catalysts are easily recoverable by filtration, and are recyclable for

  已经通过 [60] 富勒烯和相应醛的 Prato 反应制备了三种源自天然缬氨酸、苯丙氨酸和叔亮氨酸的新型富勒硫脲。这些杂化物已在均相和纯条件下用作典型立体选择性硝基-迈克尔加成反应的有机催化剂。催化剂很容易通过过滤回收，并且至少可以回收五次。通过使用低至 0.5 mol% 的催化剂负载量，以优异的产率和立体选择性获得了加成产物。
• Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts
  作者：Jeremiah P. Malerich、Koji Hagihara、Viresh H. Rawal

  DOI：10.1021/ja805693p

  日期：2008.11.5

  dominant platform for hydrogen bond promoted asymmetric catalysts. A large number of reactions, reported in scores of publications, have been successfully promoted by chiral thioureas. The present paper reports the use of squaramides as a highly effective new scaffold for the development of chiral hydrogen bond donor catalysts. Squaramide catalysts are very simple to prepare. The (-)-cinchonine modified

  硫脲代表了氢键促进的不对称催化剂的主要平台。手性硫脲已经成功地促进了大量反应，在许多出版物中都有报道。本论文报道了使用方酸酰胺作为开发手性氢键供体催化剂的高效新型支架。方酸酰胺催化剂的制备非常简单。(-)-辛可宁改性方酸酰胺 (5) 很容易通过方酸甲酯通过两步法制备，即使在催化剂负载量低至 0.1 mol% 的情况下，对于 1 的共轭加成反应也显示出是一种有效的催化剂。 ,3-二羰基化合物转化为 β-硝基苯乙烯。以高产率和优异的对映选择性获得加成产物。
• Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
  作者：José M Andrés、Miriam Ceballos、Alicia Maestro、Isabel Sanz、Rafael Pedrosa

  DOI：10.3762/bjoc.12.61

  日期：——

  The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the length of the tether linking the chiral thiourea to the polymer. The best results were obtained with the thiourea derived from (L)-valine and 1,6-hexanediamine. The catalysts can be used in only 2 mol % loading, and reused for at least four cycles in neat conditions. The ball milling promoted additions also worked very well.

  不同支撑的双官能硫脲在磺酰基聚苯乙烯树脂上的催化活性已经在不同亲核试剂对反式-β-硝基苯乙烯衍生物的硝基迈克尔加成中进行了研究。催化剂的活性取决于将手性硫脲与聚合物连接的链长度。最佳结果是使用由(L)-缬氨酸和1,6-己二胺衍生的硫脲得到的。催化剂可以在仅2%的负载下使用，并在纯净条件下至少重复使用四个周期。球磨促进的加成也非常有效。