(R)-(-)-1-nitrononan-2-ol

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (R)-(-)-1-nitrononan-2-ol
• 英文别名: (2R)-1-nitrononan-2-ol
• 化学式: C₉H₁₉NO₃
• 分子量: 189.255
• InChiKey: VQBXYLSXCORZGJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 正辛醛 在 4-methyl-N-[(1R)-2-{[(1S,2S)-2-{[(2R)-2-(4-methylbenzenesulfonamido)-2-phenylethyl]amino}-1,2-diphenylethy]amino}-1-phenylethyl]benzene-1-sulfonamido 、 copper(II) acetate monohydrate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以99%的产率得到(R)-(-)-1-nitrononan-2-ol
  参考文献：
  名称：

  高效的双（磺酰胺）-二胺配体：对映选择性铜催化亨利反应的独特手性骨架

  摘要：

  壁橱里的骷髅！作为独特的手性骨架，新开发的双（磺酰胺）-二胺同时含有二胺和双（磺酰胺）部分，是不对称Cu（OAc）2催化硝基甲烷与醛之间的亨利反应的高效配体。室温下催化剂负载低（请参阅方案）。脂族和芳族醛均具有高达99％ee的出色对映选择性 。

  DOI：

  10.1002/chem.201000964

文献信息

• Catalytic asymmetric nitroaldol (Henry) reactions with copper(II)/cyclopropane-based bisoxazoline complexes
  作者：Jianyou Mao、Xin Nie、Min Wang、Qian Wang、Bing Zheng、Qinghua Bian、Jiangchun Zhong

  DOI：10.1016/j.tetasy.2012.06.014

  日期：2012.7

  A series of cyclopropane-based bisoxazolines were synthesized from (R)- and (S)-amino alcohols, and applied to copper-catalyzed enantioselective nitroaldol reactions between nitromethane and various aldehydes. The reactions generated beta-hydroxy nitroalkanes in high yields (97%) and with good enantioselectivities (up to 87% ee). The effects of the oxazoline stereocenters constructed in the Henry reactions were also studied. (C) 2012 Elsevier Ltd. All rights reserved.
• The synthesis of chiral tridentate ligands from l -proline and their application in the copper(II)-catalyzed enantioselective Henry reaction
  作者：Daqian Xu、Qiangsheng Sun、Zhengjun Quan、Wei Sun、Xicun Wang

  DOI：10.1016/j.tetasy.2017.05.013

  日期：2017.7

  A series of chiral tridentate ligands derived from readily available enantiopure L-proline were designed and synthesized. The ligands together with Cu(OAc)(2) were successfully used in asymmetric Henry reactions. Various structurally divergent aldehydes and nitromethane were converted into versatile beta-nitro alcohols in MeOH at room temperature with very good yields (up to 85%) and enantioselectivities (up to 86%). (C) 2017 Elsevier Ltd. All rights reserved.
• Recoverable PEG-Supported Copper Catalyst for Highly Stereocontrolled Nitroaldol Condensation
  作者：Marco Bandini、Maurizio Benaglia、Riccardo Sinisi、Simona Tommasi、Achille Umani-Ronchi

  DOI：10.1021/ol070636w

  日期：2007.5.1

  A new poly(ethylene glycol)-modified DAT2-Cu(OAc)(2) complex smoothly catalyzes a base-free nitroaldol condensation in a highly enantioselective manner (ee up to 93%) also in reagent-grade solvent and in the presence of air. Effective recovery and recycling (up to five runs) of supported catalysts are documented.
• Enantioselective Henry reaction catalyzed by trianglamine–Cu(OAc)2 complex under solvent-free conditions
  作者：Koichi Tanaka、Satoshi Hachiken

  DOI：10.1016/j.tetlet.2008.02.113

  日期：2008.4

  Chiral trianglamine-Cu(OAc)(2) complex was found to be an efficient catalyst for enantioselective Henry reaction between nitromethane and various aldehydes to provide beta-hydroxynitoroalkanes with high enantiomeric excesses under solvent-free conditions. (c) 2008 Elsevier Ltd. All rights reserved.
• Effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward asymmetric nitroaldol reactions
  作者：Masanam Kannan、Tharmalingam Punniyamurthy

  DOI：10.1016/j.tetasy.2014.07.013

  日期：2014.10

  The synthesis and effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward nitroaldol reactions of nitromethane with various aldehydes have been described. The salan complexes exhibit superior results compared to the salalen and salalan complexes; the nature of the N,N-substituents is crucial for the enantioselectivity of the target nitroaldol products. (C) 2014 Elsevier Ltd. All rights reserved.