(S)-2-((R)-1-(furan-3-yl)-2-nitroethyl)cyclohexanone | 1023279-53-9

• 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: (S)-2-((R)-1-(furan-3-yl)-2-nitroethyl)cyclohexanone
• 英文别名: (2S)-2-[(1R)-1-(furan-3-yl)-2-nitroethyl]cyclohexan-1-one
• CAS: 1023279-53-9
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: JBAOVYDUOVKERP-QWRGUYRKSA-N

物化性质

• 熔点：
  61-63 °C
• 沸点：
  385.4±22.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环己酮 、 1-(3-呋喃基)-2-硝基乙烯 在 (S)-2-((diphenylphosphoryl)methyl)pyrrolidine 作用下， 反应 13.0h， 以98%的产率得到(S)-2-((R)-1-(furan-3-yl)-2-nitroethyl)cyclohexanone
  参考文献：
  名称：

  有机催化剂的合理设计：环酮对硝基烯烃的高度立体选择性迈克尔加成

  摘要：

  已经开发了一种出色的有机催化剂，该催化剂以优异的立体选择性（98：2至> 99：1 dr，92％至> 99％ee）促进将环酮不对称迈克尔加成至硝基烯烃，并提供了各种类型的合成的光学活性硝基烷衍生物和生物学重要性。在室温下极其简单和实用的操作程序增加了该反应的吸引力。

  DOI：

  10.1021/ol900330p

文献信息

• Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction
  作者：Chandan K. Mahato、Sayan Mukherjee、Mrinalkanti Kundu、Animesh Pramanik

  DOI：10.1021/acs.joc.8b02393

  日期：2019.1.18

  Pyrrolidine-oxadiazolone based organocatalysts are envisaged, synthesized, and utilized for asymmetric Michael reactions. Results of the investigations suggest that some of the catalysts are indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to 99%) in high chemical yields (up to 97%) often in short reaction time. As an extension, one enantiopure Michael adduct has been utilized to

  设想，合成并基于吡咯烷-恶二唑酮的有机催化剂用于不对称迈克尔反应。研究结果表明，某些催化剂在短时间反应中通常以高化学收率（高达97％）的确对立体选择性1,4共轭迈克尔加成反应（dr：> 97：3，ee高达99％）有效。时间。作为扩展，已使用一种对映纯迈克尔加合物来合成旋光的八氢吲哚。
• Prolinol Sulfinyl Ester Derivatives: Organocatalytic Michael Addition of Ketones to Nitroolefins under Neat Conditions
  作者：Guofu Zhong、Xiaofei Zeng

  DOI：10.1055/s-0029-1216637

  日期：——

  Highly enantioselective and diastereoselective Michael addition of ketones to nitroolefins catalyzed by prolinol sulfinyl ester was achieved in excellent yields under solvent-free conditions at room temperature. catalysis - asymmetric synthesis - ketones - sulfinates - Michael additions - nitro compounds

  在室温下在无溶剂条件下以优异的收率实现了将酮高度地对映选择性和非对映选择性地将迈克尔加成到硝基烯烃上。 催化-不对称合成-酮-亚磺酸盐-迈克尔加成-硝基化合物
• l-Prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins
  作者：Pei Juan Chua、Bin Tan、Xiaofei Zeng、Guofu Zhong

  DOI：10.1016/j.bmcl.2009.03.076

  日期：2009.7

  versatile catalysts in many reactions, l-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first l-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13–>99:1) and enantioselectivities (82–96%).

  尽管已经证明许多手性胺例如1-脯氨酸及其衍生物在许多反应中是通用催化剂，但是1-脯氨醇很少用作反应的有机催化剂。在本文中，我们报道了第一升-prolinol催化不对称迈克尔加成的环己酮在苯甲酸的存在nitroolefins得到迈克尔加成物具有高非对映选择性（87：13-> 99：1）和对映选择性（82-96％）。
• Chiral pyrrolidine–triazole conjugate catalyst for asymmetric Michael and Aldol reactions
  作者：S. Chandrasekhar、Bhoopendra Tiwari、Bibhuti B. Parida、Ch. Raji Reddy

  DOI：10.1016/j.tetasy.2008.01.033

  日期：2008.3

  A new pyrrolidine-triazole conjugate organocatalyst is synthesized using a Huisgen 1,3-dipolar cycloaddition reaction. The application of this catalyst in an asymmetric Michael addition and in an Aldol reaction is described, showing good catalytic activity. The reactions proceeded to give the products in good yield and in a highly selective manner. (C) 2008 Elsevier Ltd. All rights reserved.
• Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins
  作者：Togapur Pavan Kumar、Sirinyam Venugopal Balaji

  DOI：10.1016/j.tetasy.2014.02.003

  日期：2014.3

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.