(S)-1-nitro-nonan-2-ol | 927651-11-4

• 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: (S)-1-nitro-nonan-2-ol
• 英文别名: (2S)-1-Nitrononan-2-OL
• CAS: 927651-11-4
• 化学式: C₉H₁₉NO₃
• 分子量: 189.255
• InChiKey: VQBXYLSXCORZGJ-VIFPVBQESA-N

物化性质

• 沸点：
  291.7±23.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

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 copper diacetate DAT₂ 作用下， 以 乙醇 为溶剂， 反应 40.0h， 以78%的产率得到(S)-1-nitro-nonan-2-ol
  参考文献：
  名称：

  新型手性铜配合物催化的高度对映选择性的硝基羟醛反应。

  摘要：

  描述了DATs / Cu催化剂用于对映选择性硝基羟醛反应的显着通用性；记录了一系列醛的优异的立体诱导水平（ee 81-99％，17个实例），并证明了采用本催化体系作为制备高度官能化的四氢异喹啉的关键步骤的可能性。

  DOI：

  10.1039/b613019d

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.
• Highly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes
  作者：Marco Bandini、Fabio Piccinelli、Simona Tommasi、Achille Umani-Ronchi、Caterina Ventrici

  DOI：10.1039/b613019d

  日期：——

  Remarkable generality in scope of DATs/Cu catalysts for enantioselective nitroaldol reaction is described; excellent levels of stereoinduction are recorded for a range of aldehydes (ee 81-99%, 17 examples) and the possibility to employ the present catalytic system as the key step for the preparation of highly functionalized tetrahydro-isoquinolines is demonstrated.

  描述了DATs / Cu催化剂用于对映选择性硝基羟醛反应的显着通用性；记录了一系列醛的优异的立体诱导水平（ee 81-99％，17个实例），并证明了采用本催化体系作为制备高度官能化的四氢异喹啉的关键步骤的可能性。