(R)-2-((S)-1-(furan-3-yl)-2-nitroethyl)cyclohexanone

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

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 、 3-(2-nitrovinyl)furan 在 (S)-1-(pyrrolidine-2-ylmethyl)-1H-pyrazole 、 三氟乙酸 作用下， 反应 18.0h， 生成 (S)-2-((R)-1-(furan-3-yl)-2-nitroethyl)cyclohexanone 、 (R)-2-((S)-1-(furan-3-yl)-2-nitroethyl)cyclohexanone
  参考文献：
  名称：

  A chiral pyrrolidine-pyrazole catalyst for the enantioselective Michael addition of carbonyls to nitroolefins

  摘要：

  An enantioselective Michael reaction of carbonyl compounds to nitroolefins has been accomplished using a novel chiral pyrrolidine-pyrazole catalyst. This newly prepared catalyst was found to be very effective in providing good yields as well as good diastereo- and enantio-selectivities. The mechanism of the reaction has also been substantiated by mass spectral studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.010

文献信息

• 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.
• Pyrrolidine-oxyimides: new chiral catalysts for enantioselective Michael addition of ketones to nitroolefins in water
  作者：Togapur Pavan Kumar、Laghuvarapu Radhika、Kothapalli Haribabu、Veerjala Naveen Kumar

  DOI：10.1016/j.tetasy.2014.10.014

  日期：2014.12

  A new class of proline based organocatalysts 'pyrrolidine-oxyimides' were designed and synthesized from L-proline and hydroxyimides by employing a simple reaction protocol. These catalysts were found to be efficient in promoting asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were obtained with catalyst 1a under additive-free conditions employing water as the reaction medium. (C) 2014 Elsevier Ltd. All rights reserved.
• Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts
  作者：Chandan K. Mahato、Mrinalkanti Kundu、Animesh Pramanik

  DOI：10.1016/j.tetasy.2017.03.002

  日期：2017.4

  New chiral organocatalysts are envisaged based on a pyrrolidine-pyridone conjugate and synthesized from commercially available proline employing standard protocols. These catalysts were found to be useful for asymmetric Michael additions of ketones to nitroolefins to afford the desired products in very good yields (up to 98%) with excellent diastereo- and enantioselectivities (>97:3 syn/anti and up to 98% ee) in very short reaction time compared with the existing reports. (C) 2017 Elsevier Ltd. All rights reserved.
• Pyrrolidine-HOBt: an oxytriazole catalyst for the enantioselective Michael addition of cyclohexanone to nitroolefins in water
  作者：Togapur Pavan Kumar、Sthanikam Siva Prasad、Kothapalli Haribabu、Veerjala Naveen Kumar、Cirandur Suresh Reddy

  DOI：10.1016/j.tetasy.2016.08.006

  日期：2016.12

  A new analogue of the proline derived organocatalyst 'pyrrolidine-HOBt' has been designed and synthesized from L-prolinol and hydroxybenzotriazole (HOBt) employing a simple reaction protocol. The catalyst was found to be effective in promoting the asymmetric Michael addition of cyclohexanone to nitroolefins using water as the reaction medium. The reaction products gamma-nitrocarbonyls are obtained in good yields and stereoselectivities. (C) 2016 Elsevier Ltd. All rights reserved.