(R)-5-Nonyl-2-pyrrolidinone | 139617-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-5-Nonyl-2-pyrrolidinone
• 英文别名: (5R)-5-nonylpyrrolidin-2-one
• CAS: 139617-38-2
• 化学式: C₁₃H₂₅NO
• 分子量: 211.348
• InChiKey: NSGPXHNKOBMYEP-GFCCVEGCSA-N

物化性质

• 沸点：
  351.0±11.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-5-Nonyl-2-pyrrolidinone 在 正丁基锂 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.0h， 生成 (R)-N-Methoxycarbonyl-5-nonyl-2-pyrrolidinone
  参考文献：
  名称：

  Unprecedented Facial Diastereoselectivity in the Paternò-Büchi Reaction of a Chiral Dihydropyrrole—A Short Total Synthesis of (+)-Preussin

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3400::aid-anie3400>3.0.co;2-3
• 作为产物：
  描述：

  L-焦谷氨醇 在 吡啶 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 21.0h， 生成 (R)-5-Nonyl-2-pyrrolidinone
  参考文献：
  名称：

  Unprecedented Facial Diastereoselectivity in the Paternò-Büchi Reaction of a Chiral Dihydropyrrole—A Short Total Synthesis of (+)-Preussin

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3400::aid-anie3400>3.0.co;2-3

文献信息

• Enantioselective syntheses of Monomorium minutum ant venom alkaloids : (5R)-2-(5-Hexenyl)-5-nonyl-3,4-dihydro-2H-pyrrole and (2R,5R)-2-(5-hexenyl)-5-nonylpyrrolidine from (s)-pyroglutamic acid.
  作者：S. Rosset、J.P. Célérier、G. Lhommet

  DOI：10.1016/0040-4039(91)80523-9

  日期：1991.12

  We describe enantioselective syntheses of 2,5-disubstituted pyrroline and pyrrolidine with unsaturated radical, starting from (S)-pyroglutamic acid.

  我们描述了从（S）-焦谷氨酸开始的具有不饱和基团的2,5-二取代的吡咯啉和吡咯烷的对映选择性合成。
• The Synthesis of (+)-Preussin and Related Pyrrolidinols by Diastereoselective Paternò-Büchi Reactions of Chiral 2-Substituted 2,3-Dihydropyrroles
  作者：Thorsten Bach、Harm Brummerhop、Klaus Harms

  DOI：10.1002/1521-3765(20001016)6:20<3838::aid-chem3838>3.0.co;2-1

  日期：2000.10.16

  The N-alkoxycarbonyl substituted 2,3-dihydropyrroles 3 and 8 are converted to 2-benzyl-3-pyrrolidinols by the Paterno-Buchi reaction followed by hydrogenolysis. Since the addition of the photoexcited benzaldehyde at the unsaturated heterocycle proceeds in a syn fashion, the benzyl group at C-2 and the hydroxy group at C-3 of the product are cis oriented. The simple and facial diastereoselectivities of the Paterno-Buchi reaction were studied more closely and the relative configuration of the products was elucidated. The thermodynamically less stable endo product is formed as a result of simple diastereoselection. The face differentiation in 2-substituted 2,3-dihydropyrroles is presumably due to the nonplanarity of these heterocycles, which forces attack of the carbonyl group on the face with the existing substituent. All-cis-pyrrolidinols are consequently formed after hydrogenolysis. Following this route, a total synthesis of the pyrrolidinol alkaloid (+)-preussin (1) was conducted, which yielded the target compound in a total yield of 11% over nine steps starting from L-pyroglutaminol (11).