(+/-)-syn-2-nitro-1-phenyl-1,3-propanediol | 5285-85-8

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-syn-2-nitro-1-phenyl-1,3-propanediol
• 英文别名: (1RS,2RS)-2-nitro-1-phenyl-propane-1,3-diol；(1RS,2RS)-2-Nitro-1-phenyl-propan-1,3-diol；(R*,R*)-(1)-2-Nitro-1-phenylpropane-1,3-diol；(1S,2S)-2-nitro-1-phenylpropane-1,3-diol
• CAS: 5285-85-8
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: KAPBNJZOLYDLQK-IUCAKERBSA-N

物化性质

• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  (+/-)-syn-2-nitro-1-phenyl-1,3-propanediol 在 sodium acetate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 4-nitro-3-phenyl-4-pentenoic acid-methylester
  参考文献：
  名称：

  硝基烯烃的三氟乙酰氧基-苯基硒代区域选择性制备硝基烯丙醇衍生物及其作为多种偶联剂的用途

  摘要：

  在以前的论文中已经表明，具有烯丙基离去基团的硝基烯烃2-硝基-2-丙烯-1-醇（NPP，1）的新戊酸酯可以用作通用的多重偶联试剂。本贡献描述了在烯丙基碳骨架的1-位和/或3-位取代的NPP类似物的制备。硝基脂族化学的标准方法很容易提供对称取代的衍生物，例如环己烯（7）和茚基（8），而非对称衍生物则不容易制备，例如苯基NPP 9。现在，通过将烯丙基新戊酰氧基引入硝基烯烃的区域选择性方法极大地改善了这种情况：在四步序列的第一步中，在硝基烯烃双键之间添加了苯基硒基和三氟乙酰氧基（10→11），然后，3 ·醚化（→14）。-用取代的NPP型试剂对各种亲核试剂进行硝基烯丙基化的产物16-34的区域选择性制备证明了这些多重偶联试剂的广泛应用范围。由于硝基的大量转化，这些试剂提供了无NO 2-取代基的各种结构的途径，请参见。参见图2和3。讨论了NPP衍生物的反应机理。

  DOI：

  10.1016/s0040-4020(01)96725-0
• 作为产物：
  描述：

  (1RS,2RS)-1,3-diacetoxy-2-nitro-1-phenyl-propane 在 盐酸 、 丙酮 作用下， 生成 (+/-)-syn-2-nitro-1-phenyl-1,3-propanediol
  参考文献：
  名称：

  Fodor et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1955, p. 441,445; engl. Ausg. S. 391, 394

  摘要：

  DOI：

文献信息

• Synthesis and reactions of substituted nitro-allylating reagents
  作者：Paul Knochel、Dieter Seebach

  DOI：10.1016/s0040-4039(00)87737-0

  日期：——
• l-2-Nitro-1,3-alkanediols by stereoselective addition of nitroethanol to aldehydes. On the asymmetric electrophilic addition to double bonds
  作者：Martin Eyer、Dieter Seebach

  DOI：10.1021/ja00298a033

  日期：1985.6
• Quantitative Evaluation of the Catalytic Activity of Dendrimers with Only One Active Center at the Core:  Application to the Nitroaldol (Henry) Reaction
  作者：Aizpea Zubia、Fernando P. Cossío、Iñaki Morao、Marina Rieumont、Xabier Lopez

  DOI：10.1021/ja039888s

  日期：2004.4.28

  One reference tertiary amine and three families of structurally related trialkylamines and dendrimers have been synthesized, characterized, and studied by molecular dynamics simulations. The catalytic activity of these amines in the nitroaldol (Henry) reaction between 2-nitroethanol and benzaldehyde has been measured by FT-IR spectroscopy. It is found that, in this kind of molecule with only one catalytic center at the core, the efficiency of the catalytic process decreases with the size and/or the degree of ramification of the dendrimer. According to these results, there is a linear departure from the behavior predicted by the hard sphere collision theory (HSCT) as the size of the dendrimer increases. Therefore, the behavior of structurally related dendrimers can be quantified in terms of their molecular weight and reagent accessible surfaces.
• Dendritic Catalysts for the Nitroaldol (Henry) Reaction
  作者：Iñaki Morao、Fernando P Cossío

  DOI：10.1016/s0040-4039(97)01477-9

  日期：1997.9

  Dendritic molecules with a single triethylene amine core surrounded by hyperbranched polyether sectors catalyze the nitroaldol reaction between aromatic aldehydes and nitroalkanes. (C) 1997 Elsevier Science Ltd.
• Configurational analysis of diastereomeric open-chain and cyclic nitro-substituted diols by NMR spectroscopy
  作者：P. Sohár、Gy. Mikite、I. Pelczer、Á. Kovács、A. Kis-Tamás

  DOI：10.1002/mrc.1270221109

  日期：1984.11

  AbstractNitro‐substituted 1,3‐dioxanes and pyrans with potential biological activity were synthesized. The relative configurations of the threo and erythro isomers of 2‐nitro‐1‐phenylpropane‐1,3‐diol (the starting materials) and of 5‐nitro‐2,4‐diphenyl‐1,3‐dioxane, the products formed with benzaldehyde, were determined by 1H and 13C NMR spectroscopy. Cinnamaldehyde and nitroethanol give a homologue of nitrophenylpropanediol, which exists as a mixture of two diastereomeric cyclic hemiacetals. After dissolving in CDCl3, the ratio of these components changes from approximately 10:1 to 3:2 in a few days. The ethyl acetal of the hemiacetal is stereohomogeneous, and the ethoxy group is axial to the pyran ring owing to the anomeric effect. This configuration was proved by two‐dimensional NMR measurement, permitting separate observation of the originally overlapping multiplets and direct reading of the H,H coupling constants.