(R)-(-)-4-hydroxynonanenitrile | 136118-33-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-4-hydroxynonanenitrile
• 英文别名: (4R)-4-hydroxynonanenitrile
• CAS: 136118-33-7
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: FIEQCVFGYSICRN-SECBINFHSA-N

物化性质

• 沸点：
  281.8±23.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-4-hydroxynonanenitrile 在 氢氧化钾 作用下， 以 2-甲基-2-丁醇 为溶剂， 以0.134 g的产率得到4-hydroxynonanoic acid
  参考文献：
  名称：

  Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone

  摘要：

  Regiospecific C-5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C-6- substitution product. A stereoselective synthetic scheme for (+)-gamma-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.

  DOI：

  10.1023/b:conc.0000018110.36123.f2
• 作为产物：
  描述：

  (R)-(E)-(-)-4-Hydroxy-2-nonenenitrile 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 36.0h， 以97%的产率得到(R)-(-)-4-hydroxynonanenitrile
  参考文献：
  名称：

  Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone

  摘要：

  Regiospecific C-5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C-6- substitution product. A stereoselective synthetic scheme for (+)-gamma-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.

  DOI：

  10.1023/b:conc.0000018110.36123.f2

文献信息

• Bakers' Yeast Reduction of γ and δ Ketonitriles: Intermediates for the Synthesis of (S)-5-Hexanolide and Other Chiral Lactones
  作者：Aravamudan Gopalan、Richard Lucero、Hollie Jacobs、Kent Berryman

  DOI：10.1080/00397919108021279

  日期：1991.6

  yeast carefully studied. Both 4-oxopentanenitrile and 5-oxohexanenitrile are reduced in moderate yields to the corresponding (S) alcohols of high ee while other substrates gave products of varying optical purities. These alcohols are useful intermediates for the preparation of chiral lactones, including the synthetically important (S)(−)-4-methylbutyrolactone and (S)-(−)-5-hexanolide.

  摘要 已经合成了许多 γ 和 δ 酮腈，并仔细研究了它们用面包酵母的还原。4-氧代戊腈和 5-氧代己腈均以中等产率还原为相应的高 ee (S) 醇，而其他底物产生不同光学纯度的产物。这些醇是制备手性内酯的有用中间体，包括合成重要的 (S)(-)-4-甲基丁内酯和 (S)-(-)-5-己内酯。
• Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone
  作者：F. A. Valeev、E. V. Gorobets、I. P. Tsypysheva、G. Sh. Singizova、L. Kh. Kalimullina、M. G. Safarov、O. V. Shitikova、M. S. Miftakhov

  DOI：10.1023/b:conc.0000018110.36123.f2

  日期：2003.11

  Regiospecific C-5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C-6- substitution product. A stereoselective synthetic scheme for (+)-gamma-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.