(2R)-2-[(S)-2-nitro-1-(thiophen-2-yl)ethyl]pentanal

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2R)-2-[(S)-2-nitro-1-(thiophen-2-yl)ethyl]pentanal
• 英文别名: (R)-2-((S)-2-nitro-1-(thiophen-2-yl)ethyl)pentanal；(2R)-2-[(1R)-2-nitro-1-thiophen-2-ylethyl]pentanal
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: LFPLOYSWIQUDET-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-硝基乙烯基噻吩 、 正戊醛 在 (2S,4R)-4-hydroxy-N-[(S)-1-hydroxy-1,1,3-triphenylpropan-2-yl]pyrrolidine-2-carboxamide 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以96%的产率得到(2R)-2-[(S)-2-nitro-1-(thiophen-2-yl)ethyl]pentanal
  参考文献：
  名称：

  Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions

  摘要：

  4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.122

文献信息

• Unique β‐Turn Peptoid Structures and Their Application as Asymmetric Catalysts
  作者：Chandra Mohan Darapaneni、Pritam Ghosh、Totan Ghosh、Galia Maayan

  DOI：10.1002/chem.202000595

  日期：2020.8.3

  Peptoids, N‐substituted glycine oligomers, represent an important class of peptidomimetics that can fold into three‐dimensional structures in solution. Most of the folded peptoid structures, however, resemble helices, and this can limit their applications, specifically in asymmetric catalysis. In this work, for the first time, unique examples of pyrrolidine‐based β‐turn‐like peptoids are described

  类肽，N-取代的甘氨酸低聚物，代表了一类重要的拟肽，可以在溶液中折叠成三维结构。然而，大多数折叠的类肽结构类似于螺旋，这可能限制了它们的应用，特别是在不对称催化中。在这项工作中，首次描述了吡咯烷类β-turn类肽的独特实例，并在固态，单晶X射线分析和溶液中通过圆二色光谱进行了表征。此外，还证明了它们通过在水中的不对称迈克尔反应产生γ-硝基醛的高效和对映选择性催化活性。新的β-turn-like类肽的结构性质和DFT-D3计算，
• Enantioselective Michael addition of aldehydes to nitroolefins catalyzed by pyrrolidine-HOBt
  作者：Togapur Pavan Kumar、Mohammad Abdul Sattar、Sthanikam Siva Prasad、Kothapalli Haribabu、Cirandur Suresh Reddy

  DOI：10.1016/j.tetasy.2017.02.005

  日期：2017.3

  The oxytriazole catalyst "pyrrolidine-HOBt" developed for asymmetric Michael addition of cyclohexanone to nitroolefins is now evaluated for the asymmetric Michael addition of aldehydes to nitroolefins under similar reaction conditions. The results of this study indicate that, the oxytriazole catalyst "pyrrolidine-HOBt" is equally effective in promoting the Michael addition of aldehydes to nitroolefins on employing benzoic acid as an additive. The desired products, gamma-nitrocarbonyl compounds were obtained in good yields and high enantioselectivities. (C) 2017 Elsevier Ltd. All rights reserved.
• Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Simpletrans-4-Hydroxyprolylamide
  作者：Claudio Palomo、Silvia Vera、Antonia Mielgo、Enrique Gómez-Bengoa

  DOI：10.1002/anie.200602207

  日期：2006.9.11
• Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by a pyrrolidine–pyrazole
  作者：Togapur Pavan Kumar

  DOI：10.1016/j.tetasy.2014.07.005

  日期：2014.10

  An effective protocol for the stereoselective Michael addition of aldehydes to nitroolefins using pyrrolidine-pyrazole as an organocatalyst is described. The catalytic cycle was found to be productive in terms of yield and selectivity, when performed under solvent-free reaction conditions and employing 15 mol % of catalyst and 10 mol % of benzoic acid at room temperature. (C) 2014 Elsevier Ltd. All rights reserved.
• Organocatalytic activity of 4-hydroxy-prolinamide alcohol with different noncovalent coordination sites in asymmetric Michael and direct aldol reactions
  作者：Yuko Okuyama、Hiroto Nakano、Yuki Watanabe、Mika Makabe、Mitsuhiro Takeshita、Koji Uwai、Chizuko Kabuto、Eunsang Kwon

  DOI：10.1016/j.tetlet.2008.10.122

  日期：2009.1

  4-Hydroxy-prolinamide alcohol with different noncoordination sites as a molecule showed excellent asymmetric catalytic activity in both the Michael reaction (up to 98% ee) and the direct aldol reaction (up to >99% ee), and the catalyzing reactions with high enantioselectivity are supported by a DFT theoretical study of their transition state. (C) 2008 Elsevier Ltd. All rights reserved.