3-nitromethyl-pentan-3-ol | 156544-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-nitromethyl-pentan-3-ol
• 英文别名: 3-(Nitromethyl)pentan-3-ol
• CAS: 156544-56-8
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: YLBJVOGWRMXWET-UHFFFAOYSA-N

物化性质

• 沸点：
  72.5-73 °C(Press: 1 Torr)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 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：

  3-nitromethyl-pentan-3-ol 在 硫酸 、 potassium methanolate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 2-ethyl-1-nitrobut-1-ene
  参考文献：
  名称：

  从 β-硝基叔醇合成 DI-和三取代 α-硝基烯烃的便捷两步法

  摘要：

  摘要 根据 R2 的性质，用乙酸酐和 1 当量的甲醇钾或叔丁醇处理由 α-亚硝基锂加成到酮中得到的叔 β-硝基醇 I，得到良好的 α-硝基烯烃 III产量。

  DOI：

  10.1080/00397919608003835
• 作为产物：
  描述：

  硝基甲烷 、 3-戊酮 在 P(i-PrNCH₂CH₂)3N 、 magnesium sulfate 作用下， 反应 3.0h， 以67%的产率得到3-nitromethyl-pentan-3-ol
  参考文献：
  名称：

  P(RNCH₂CH₂)₃N:  An Efficient Promoter for the Nitroaldol (Henry) Reaction

  摘要：

  The use of catalytic amounts of the proazaphosphatranes P(MeNCH2CH2)(3)N, P(i-PrNCH2CH2)(3)N and P(HNCH2CN2)(i-PrNCH2CH2)(2)N as nonionic bases in the reaction of nitroalkanes with carbonyl compounds is reported. The reaction proceeds at room temperature in the presence of 2.2 equiv of magnesium sulfate to produce the corresponding beta-nitroalkanols in generally superior yields. Aldehydes react quantitatively in 5-60 min, whereas ketones require up to 3 h to react with nitromethane and up to 7 h for the reaction of ketones with higher nitroalkanes.

  DOI：

  10.1021/jo9818733

文献信息

• Synthesis of new proazaphosphatranes and their application in organic synthesis
  作者：Philip B. Kisanga、John G. Verkade

  DOI：10.1016/s0040-4020(00)01016-4

  日期：2001.1

  We report herein the synthesis of the new proazaphosphatrane strong bases P(RNCH2CH2)(3)N (R=Me3CCH2, Me2CHCH2) and P(HNCH2CH2)(2)NCH2CH2N-i-Pr (1g). The new azaphosphatranes [HP(RNCH2CH2)(3)N]Cl (R=Me3CCH2, Me2CHCH2)have P-N-ax distances of 2.047 and 1.958 Angstrom, respectively. We also report the synthesis of the tetramine precursor proazaphosphatrane 1g [namely, (H2NCH2CH2)(2)NCH2CH2NH-i-Pr] in 41% yield and the use of a complexation-extraction technique to separate it from a mixture containing the di- and tri-isopropyl substituted analogs. Using a P-31 NMR technique, we report the pK(a) value for 1gH(+) (34.49). The catalytic properties of three bases P(RNCH2CH2)(3)N (R=i-Pr, Piv, i-Bu) are compared in the synthesis of several beta -hydroxy nitriles, beta -nitroalkanols, alpha,beta -unsaturated esters and for the Michael addition of allyl alcohol to alpha,beta -unsaturate ketones. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Golding, Peter; Powell, Joy L.; Ridd, John H., Journal of the Chemical Society. Perkin transactions II, 1996, # 5, p. 813 - 820
  作者：Golding, Peter、Powell, Joy L.、Ridd, John H.

  DOI：——

  日期：——
• Porter; Wood, Journal of the Institute of Petroleum, 1951, vol. 37, p. 388,391
  作者：Porter、Wood

  DOI：——

  日期：——
• Michel,J. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964, vol. 258, p. 6171 - 6174
  作者：Michel,J. et al.

  DOI：——

  日期：——
• P(RNCH₂CH₂)₃N:  An Efficient Promoter for the Nitroaldol (Henry) Reaction
  作者：Philip B. Kisanga、John G. Verkade

  DOI：10.1021/jo9818733

  日期：1999.6.1

  The use of catalytic amounts of the proazaphosphatranes P(MeNCH2CH2)(3)N, P(i-PrNCH2CH2)(3)N and P(HNCH2CN2)(i-PrNCH2CH2)(2)N as nonionic bases in the reaction of nitroalkanes with carbonyl compounds is reported. The reaction proceeds at room temperature in the presence of 2.2 equiv of magnesium sulfate to produce the corresponding beta-nitroalkanols in generally superior yields. Aldehydes react quantitatively in 5-60 min, whereas ketones require up to 3 h to react with nitromethane and up to 7 h for the reaction of ketones with higher nitroalkanes.