2,4-dimethyl-1-nitropentan-2-ol | 882041-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dimethyl-1-nitropentan-2-ol
• 英文别名: 2,4-dimethyl-1-nitro-2-pentanol
• CAS: 882041-34-1
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: JYPKKZLZLXBBPG-UHFFFAOYSA-N

物化性质

• 沸点：
  243.8±23.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  2,4-dimethyl-1-nitropentan-2-ol 在 (S)-La-Li₃-(binaphthoxide)3 、 C₄₂H₃₆LaLi₃O₁₂ 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以40%的产率得到(R)-2,4-dimethyl-1-nitro-2-pentanol
  参考文献：
  名称：

  Mixed La–Li heterobimetallic complexes for tertiary nitroaldol resolution

  摘要：

  Full details of the kinetic resolution of tertiary nitroaldols derived from simple ketones are described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. Using a 2:1 mixture of La-Li-3-(binaphthoxide 1a)(3) complex (LLB) and La-Li-3-(biphenoxide 1e)(3) complex, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Transformations of products were also investigated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.031
• 作为产物：
  描述：

  硝基甲烷 、 4-甲基-2-戊酮 在 三乙烯二胺 、 lithium bromide 作用下， 反应 0.08h， 以63%的产率得到2,4-dimethyl-1-nitropentan-2-ol
  参考文献：
  名称：

  Rapid Microwave-Assisted Henry Reaction in Solvent-Free Processes

  摘要：

  在微波辐照下研究了硝基甲烷与一系列羰基化合物的无溶剂亨利反应。通过使用不同的碱和路易斯酸，在微波条件下实现了醛类化合物的无溶剂硝基甲醇反应，并得到了相应的高产率加合物。特别是在类似条件下，使用 1,4-二氮杂双环[2.2.2]辛烷（DABCO）作为硝基甲醛醇反应的反应底物，可以得到相应的加合物，且收率中等至良好。

  DOI：

  10.1055/s-2006-932449

文献信息

• Mixed La−Li Heterobimetallic Complexes for Tertiary Nitroaldol Resolution
  作者：Shin-ya Tosaki、Keiichi Hara、Vijay Gnanadesikan、Hiroyuki Morimoto、Shinji Harada、Mari Sugita、Noriyuki Yamagiwa、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja064858l

  日期：2006.9.1

  A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield.
• Mixed La–Li heterobimetallic complexes for tertiary nitroaldol resolution
  作者：Keiichi Hara、Shin-ya Tosaki、Vijay Gnanadesikan、Hiroyuki Morimoto、Shinji Harada、Mari Sugita、Noriyuki Yamagiwa、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2009.02.031

  日期：2009.6

  Full details of the kinetic resolution of tertiary nitroaldols derived from simple ketones are described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. Using a 2:1 mixture of La-Li-3-(binaphthoxide 1a)(3) complex (LLB) and La-Li-3-(biphenoxide 1e)(3) complex, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Transformations of products were also investigated. (C) 2009 Elsevier Ltd. All rights reserved.
• Rapid Microwave-Assisted Henry Reaction in Solvent-Free Processes
  作者：Zhiyong Wang、Changsheng Gan、Xing Chen、Guoyin Lai

  DOI：10.1055/s-2006-932449

  日期：——

  The solvent-free Henry reactions of nitromethane with a series of carbonyl compounds were studied under microwave irradiation. By using different bases and Lewis acids, the solvent-free nitroaldol reaction of aldehydes were realized under microwave condition, affording the corresponding adducts with high yields. Particularly, aliphatic ketones, which were hardly carried out this reaction, could be the reaction substrates in the nitroaldol reactions by employment of 1,4-diazabicyclo[2.2.2]octane (DABCO) under a similar conditions, giving the corresponding adducts with moderate to good yields.

  在微波辐照下研究了硝基甲烷与一系列羰基化合物的无溶剂亨利反应。通过使用不同的碱和路易斯酸，在微波条件下实现了醛类化合物的无溶剂硝基甲醇反应，并得到了相应的高产率加合物。特别是在类似条件下，使用 1,4-二氮杂双环[2.2.2]辛烷（DABCO）作为硝基甲醛醇反应的反应底物，可以得到相应的加合物，且收率中等至良好。