4-hydroxy-3-methylidenenonan-2-one | 108762-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxy-3-methylidenenonan-2-one
• 英文别名: 4-hydroxy-3-methylenenonan-2-one
• CAS: 108762-27-2
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: XSKPTZTXVMVYQX-UHFFFAOYSA-N

物化性质

• 沸点：
  74-77 °C(Press: 0.5 Torr)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methylidenenonan-2-one 生成 2-壬烷酮,4-羟基-3-甲基-,(3R,4S)-
  参考文献：
  名称：

  UTAKA MASANORI; ONOUE SHINJI; TAKEDA AKIRA, CHEM. LETT.,(1987) N 5, 971-972

  摘要：

  DOI：
• 作为产物：
  描述：

  丁烯酮 、 正己醛 在 六氟异丙醇 、 1-十六烷基咪唑 作用下， 以 水 为溶剂， 反应 24.0h， 以62%的产率得到4-hydroxy-3-methylidenenonan-2-one
  参考文献：
  名称：

  Morita-Baylis-Hillman Reaction on Water without Organic Solvent, Assisted by a ‘Catalytic’ Amount of Amphiphilic Imidazole Derivatives

  摘要：

  可以使用两性N-烷基咪唑在无任何有机溶剂的情况下，以水作为溶剂进行Morita-Baylis-Hillman (MBH)反应。随着水的添加，该反应得以加速，这是在水存在下进行的第一个没有有机溶剂的“催化”MBH反应的例子。

  DOI：

  10.1055/s-0029-1216944

文献信息

• <i>N</i>-Alkylimidazole as Amphiphilic Organocatalyst: ‘Catalytic’ Morita-Baylis-Hillman Reaction on Water without Organic Solvent
  作者：Seijiro Matsubara、Keisuke Asano

  DOI：10.1055/s-0028-1087484

  日期：——

  In the presence of water, a Morita-Baylis-Hillman reaction between methyl vinyl ketone and various aldehydes was performed with a catalytic amount of an imidazole carrying a hydrophobic group.

  在有水的情况下，甲基乙烯基酮和各种醛在带有疏水基团的咪唑催化下发生了 Morita-Baylis-Hillman 反应。
• Asymmetric Reduction of α-Methylene Ketones by Using Fermenting Baker’s Yeast. Preparation of Optically Active β-Hydroxy α-Methyl Ketones
  作者：Masanori Utaka、Shinji Onoue、Akira Takeda

  DOI：10.1246/cl.1987.971

  日期：1987.5.5

  Asymmetric reduction of 4-hydroxy-3-methylenealkan-2-ones with baker’s yeast afforded (3R,4S)-4-hydroxy-3-methylalkan-2-ones in >98% ee and the (3R,4R) isomers in 67→98% ee in ratios of 1:1–2.

  用面包酵母不对称还原 4-hydroxy-3-methylenealkan-2-ones 得到 (3R,4S)-4-hydroxy-3-methylalkan-2-ones > 98% ee 和 (3R,4R) 异构体在 67 →98% ee，比例为 1:1–2。
• Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
  作者：Bruno R.S. de Paula、Dávila S. Zampieri、J. Augusto R. Rodrigues、Paulo J.S. Moran

  DOI：10.1016/j.tetasy.2013.07.007

  日期：2013.9

  Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten-2-one (R = n-pentyl, phenyl, 2'- and 4'-chlorophenyl, 3'- and 4'-nitrophenyl, 4'-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae and Geotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.
• Sulpholane––A new solvent for the Baylis–Hillman reaction
  作者：Palakodety Radha Krishna、A. Manjuvani、V. Kannan、G.V.M. Sharma

  DOI：10.1016/j.tetlet.2003.11.137

  日期：2004.2

  Sulpholane, a commercially available solvent, is used for the first time as a new solvent for the Baylis-Hillman reaction tinder ambient conditions; a wide variety of olefins as well as aldehydes participate very efficiently resulting in good to excellent yields of products. Acrylamide also underwent the Baylis-Hillman reaction with 4-nitrobenzaldehyde under these reaction conditions. (C) 2003 Elsevier Ltd. All rights reserved.
• Basavaiah, Deevi; Gowriswari, Vellanki V. L.; Dharma Rao, Polisetti, Journal of Chemical Research, Miniprint, 1995, # 7, p. 1656 - 1673
  作者：Basavaiah, Deevi、Gowriswari, Vellanki V. L.、Dharma Rao, Polisetti、Bharathi, Tirumala K.

  DOI：——

  日期：——