(R)-1-[2-nitro-1-(thiophen-2-yl)ethyl]cyclopentanecarbaldehyde | 1198362-27-4

• 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: (R)-1-[2-nitro-1-(thiophen-2-yl)ethyl]cyclopentanecarbaldehyde
• 英文别名: 2-cyclopentanyl-4-nitro-3-(thiophen-2-yl)butanal；1-[(1R)-2-nitro-1-thiophen-2-ylethyl]cyclopentane-1-carbaldehyde
• CAS: 1198362-27-4
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: MXAFYJCNHDWODW-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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 、 环戊基甲醛 在 (S)-1-(pyrrolidine-2-ylmethyl)-1H-pyrazole 、 苯甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 36.33h， 以89%的产率得到
  参考文献：
  名称：

  吡咯烷-吡唑催化的α，α-二取代醛对硝基烯烃的对映选择性迈克尔加成

  摘要：

  为α的不对称催化Michael加成的高效的协议，α二取代的醛与吡咯烷吡唑nitroolefins进行说明。期望的产物γ-nitrocarbonyl化合物具有全碳季中心，是在良好的产率和高对映选择性的水平的无溶剂反应条件下获得的，使用苯甲酸作为添加剂。

  DOI：

  10.1016/j.tetasy.2014.06.009

文献信息

• Enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins catalyzed by a pyrrolidine-pyrazole
  作者：Togapur Pavan Kumar、Kothapalli Haribabu

  DOI：10.1016/j.tetasy.2014.06.009

  日期：2014.8

  efficient protocol for the asymmetric catalytic Michael additions of α,α-disubstituted aldehydes to nitroolefins with a pyrrolidine-pyrazole is described. The desired products γ-nitrocarbonyl compounds possessing an all-carbon quaternary center, were obtained in good yields and with high levels of enantioselectivities under solvent-free reaction conditions, employing benzoic acid as an additive.

  为α的不对称催化Michael加成的高效的协议，α二取代的醛与吡咯烷吡唑nitroolefins进行说明。期望的产物γ-nitrocarbonyl化合物具有全碳季中心，是在良好的产率和高对映选择性的水平的无溶剂反应条件下获得的，使用苯甲酸作为添加剂。
• Pyrrolidine–oxyimide catalyzed asymmetric Michael addition of α,α-disubstituted aldehydes to nitroolefins
  作者：Togapur Pavan Kumar

  DOI：10.1016/j.tetasy.2015.07.009

  日期：2015.9

  Organocatalytic enantioselective Michael addition of α,α-disubstituted aldehydes onto nitroolefins using pyrrolidine–oxyimide catalyst was reported. The reaction works effectively under neat conditions with 15 mol % of catalyst and 10 mol % of p-nitrobenzoic acid as an additive at 0 °C; this results in the formation of Michael adducts possessing an all-carbon quaternary center with good yields and

  报道了使用吡咯烷-氧酰亚胺催化剂将α，α-二取代醛有机催化对映选择性迈克尔加成到硝基烯烃上。该反应在纯净条件下在0°C下以15 mol％的催化剂和10 mol％的对硝基苯甲酸为添加剂可有效地进行；这导致形成具有全碳四元中心并具有良好收率和对映选择性的迈克尔加合物。
• Pyrrolidinyl-Camphor Derivatives as a New Class of Organocatalyst for Direct Asymmetric Michael Addition of Aldehydes and Ketones to β-Nitroalkenes
  作者：Ying-Fang Ting、Chihliang Chang、Raju Jannapu Reddy、Dhananjay R. Magar、Kwunmin Chen

  DOI：10.1002/chem.201000483

  日期：——

  Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl–camphor derivatives (7 a–h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical α,α‐disubstituted aldehydes to β‐nitroalkenes. When this asymmetric transformation was catalyzed by organocatalyst 7 f, the desired Michael adducts were obtained in

  已经开发了实用且方便的合成路线来合成新型的吡咯烷基-樟脑衍生物（7 a–h）。筛选出这些新型化合物作为催化剂，将对称的α，α-二取代醛直接迈克尔加成至β-硝基烯烃。当该非对称转变是由有机催化剂催化的7 F，在高的化学产率得到所需的迈克尔加合物，具有高至优良的立体选择性（高达98：2非对映比（DR）和99％对映体过量（EE））。催化体系的范围已扩大到涵盖各种醛和酮作为供体来源。合成的应用由（S）-香茅醛，具有高立体选择性。
• Pyrrolidine-Camphor Derivative as an Organocatalyst for Asymmetic Michael Additions of α,α-Disubstituted Aldehydes to β-Nitroalkenes: Construction of Quaternary Carbon-Bearing Aldehydes under Solvent-Free Conditions
  作者：Chihliang Chang、Ssu-Hsien Li、Raju Jannapu Reddy、Kwunmin Chen

  DOI：10.1002/adsc.200800771

  日期：2009.6

  Abstractmagnified imageA novel pyrrolidine‐camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α‐disubstituted aldehydes with β‐nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent‐free conditions provided the desired Michael product possessing an all‐carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).
• 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.