(S)-3-ethyl-2-methyl-1-nitro-2-pentanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-ethyl-2-methyl-1-nitro-2-pentanol
• 英文别名: 3-ethyl-2-methyl-1-nitro-2-pentanol；(2S)-3-ethyl-2-methyl-1-nitropentan-2-ol
• 化学式: C₈H₁₇NO₃
• 分子量: 175.228
• InChiKey: SYOVDLREENPUBL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  3-ethyl-2-methyl-1-nitro-2-pentanol 在 (S)-La-Li₃-(binaphthoxide)3 、 C₄₂H₃₆LaLi₃O₁₂ 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-3-ethyl-2-methyl-1-nitro-2-pentanol 、 (R)-3-ethyl-2-methyl-1-nitro-2-pentanol 、 3-乙基-2-戊酮
  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

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.