(4R)-4-methylnonanenitrile | 162691-74-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (4R)-4-methylnonanenitrile
• 英文别名: (R)-4-methylnonanenitrile
• CAS: 162691-74-9
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: BSOVYGCDOIDGLT-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R)-4-methylnonanenitrile 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 (R)-4-methyl-1-nonanol
  参考文献：
  名称：

  Synthesis of the Mealworm Tenebrio molitor L. Pheromone

  摘要：

  Diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with 3-(bromomethyl)but-3-enoate, followed by reduction with zinc, gave homoallylic alcohol which was subjected to lactonization. Opening of the lactone ring in the latter afforded methyl (3S)-5,5-dimethoxy-3-methylpentanoate with a high yield and enantioselectivity. This compound is a valuable intermediate product in the synthesis of pheromone of the mealworm beetleTenebrio molitorL., a pest of stored cereals.

  DOI：

  10.1134/s1070428020060056
• 作为产物：
  描述：

  methyl (R)-5,5-dimethoxy-3-methylpentanoate 在 lithium aluminium tetrahydride 、 四溴化碳 、 4-甲基苯磺酸吡啶 、 magnesium 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 15.0h， 生成 (4R)-4-methylnonanenitrile
  参考文献：
  名称：

  Synthesis of the Mealworm Tenebrio molitor L. Pheromone

  摘要：

  Diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with 3-(bromomethyl)but-3-enoate, followed by reduction with zinc, gave homoallylic alcohol which was subjected to lactonization. Opening of the lactone ring in the latter afforded methyl (3S)-5,5-dimethoxy-3-methylpentanoate with a high yield and enantioselectivity. This compound is a valuable intermediate product in the synthesis of pheromone of the mealworm beetleTenebrio molitorL., a pest of stored cereals.

  DOI：

  10.1134/s1070428020060056

文献信息

• Stereoselective Synthesis of Sex Pheromone (R)-4-Methyl-1-Nonanol: Non-Cross-Linked Polystyrene Supported Oxazolidinone as a Chiral Auxiliary
  作者：Cuifen Lu、Donglai Li、Qiuyan Wang、Guichun Yang、Zuxing Chen

  DOI：10.1002/ejoc.200800758

  日期：2009.3

  (R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworm (Tenebrio Molitor L.), was synthesized by using non-cross-linked polystyrene supported oxazolidinone as a chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addition of an organocopper reagent to non-cross-linked polystyrene supported N-crotonoyoxazolidinone, and the target product was obtained in an overall

  (R)-4-Methyl-1-nonanol 是黄粉虫 (Tenebrio Molitor L.) 的性信息素，是通过使用非交联聚苯乙烯负载的恶唑烷酮作为手性助剂合成的。立体选择性合成是通过将有机铜试剂不对称迈克尔加成到非交联聚苯乙烯负载的 N-巴豆酰恶唑烷酮中来实现的，并且在七个步骤中以 41.8% 的总收率获得了目标产物，对映体过量为 98%。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Stereoselective synthesis of the sex pheromone of the yellow mealworm using (S)-4-benzyloxazolidinone as chiral auxiliary
  作者：D. L. Li、C. F. Lu、G. C. Yang、Z. X. Chen

  DOI：10.1007/s10600-010-9636-z

  日期：2010.7

  (R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworn (Tenebrio molitor L.), was synthesized with high stereoselectivity using (S)-4-benzyloxazolidinone as chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addition of organocopper reagent to N-crotoyloxazolidinone, and the target product was obtained in an overall yield of 41.8% over 7 steps.

  (R)-4-Methyl-1-nonanol 是黄粉蚧 (Tenebrio molitor L.) 的性信息素，使用 (S)-4-benzyloxazolidinone 作为手性助剂以高立体选择性合成。通过有机铜试剂与N-巴豆酰恶唑烷酮的不对称迈克尔加成实现立体选择性合成，7步得到目标产物，总收率为41.8%。
• Synthesis of the Mealworm Tenebrio molitor L. Pheromone
  作者：I. V. Mineeva

  DOI：10.1134/s1070428020060056

  日期：2020.6

  Diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with 3-(bromomethyl)but-3-enoate, followed by reduction with zinc, gave homoallylic alcohol which was subjected to lactonization. Opening of the lactone ring in the latter afforded methyl (3S)-5,5-dimethoxy-3-methylpentanoate with a high yield and enantioselectivity. This compound is a valuable intermediate product in the synthesis of pheromone of the mealworm beetleTenebrio molitorL., a pest of stored cereals.