3,4-dihydro-5-hexyl-2H-pyrrole | 116437-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3,4-dihydro-5-hexyl-2H-pyrrole
• 英文别名: 2-hexyl-1-pyrroline；5-hexyl-3,4-dihydro-2H-pyrrole
• CAS: 116437-48-0
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: IRBCXYVCZZHONL-UHFFFAOYSA-N

物化性质

• 沸点：
  212.0±9.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-5-hexyl-2H-pyrrole 在 (R,R,R)-bis(1-methyl-4,5,6,7-tetrahydroindene)titanium 、 氢气 作用下， 65.0 ℃ 、13.79 MPa 条件下， 生成 (R)-2-Hexyl-pyrrolidine
  参考文献：
  名称：

  Asymmetric titanocene-catalyzed hydrogenation of imines

  摘要：

  DOI：

  10.1021/ja00045a038
• 作为产物：
  描述：

  tert-butyl (N-(4-oxodecyl)amino)methanoate 在 sodium hydroxide 、 三氟乙酸 作用下， 生成 3,4-dihydro-5-hexyl-2H-pyrrole
  参考文献：
  名称：

  Organometallic ring-opening reactions of N-acyl and N-alkoxycarbonyl lactams. Synthesis of cyclic imines

  摘要：

  DOI：

  10.1021/jo00262a048

文献信息

• From Cycloalkanols to Heterocycles via Nitrogen Insertion
  作者：Alexander Sandvoß、Johannes M. Wahl

  DOI：10.1021/acs.orglett.3c02048

  日期：2023.8.11

  transition-metal-free nitrogen insertion provides access to a variety of medicinally relevant heterocycles such as pyrrolidenes, quinolines, and benzazepines (24 examples). Furthermore, combination with a photochemical Norrish–Yang-type cyclization allows an unprecedented access to indoles from ortho-substituted acetophenones.

  发现多种环醇通过O-异三叉基磺酰基羟胺进行氮插入。成功过程的关键是使用氟化醇溶剂，这可确保充分的底物活化，以允许与两亲性胺化剂结合。这种无过渡金属的氮插入提供了获得各种医学相关杂环的途径，例如吡咯烷、喹啉和苯并氮杂环（24 个例子）。此外，与光化学诺里什-杨型环化相结合，可以前所未有地从邻位取代的苯乙酮中获得吲哚。
• Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations
  作者：Christopher A. Willoughby、Stephen L. Buchwald

  DOI：10.1021/ja00099a012

  日期：1994.10

  The asymmetric hydrogenation of imines with a chiral titanocene catalyst derived from Brintzinger's ansatitanocene complex 1 proceeds to afford amines with good to excellent enantioselectivity. The catalyst is particularly effective for the reduction of cyclic imines. For these substrates enantiomeric excesses from 95 to 99% were achieved. For acyclic imines lower enantiomeric excesses were observed. The reason for this is likely due to the fact that the acyclic imines are mixtures of anti and syn isomers which interconvert during the reaction. The catalyst was found to be tolerant of many functional groups found in organic synthesis. Thus the reaction represents an effective method for the synthesis of chiral cyclic amines.
• GIOVANNINI, ARIANNA;SAVOIA, DIEGO;UMANI-RONCHI, ACHILLE, J. ORG. CHEM., 54,(1989) N, C. 228-234
  作者：GIOVANNINI, ARIANNA、SAVOIA, DIEGO、UMANI-RONCHI, ACHILLE

  DOI：——

  日期：——
• UTIMOTO, KIITIRO, PURE AND APPL. CHEM., 1983, 55, N 11, 1845-1852
  作者：UTIMOTO, KIITIRO

  DOI：——

  日期：——
• Organometallic ring-opening reactions of N-acyl and N-alkoxycarbonyl lactams. Synthesis of cyclic imines
  作者：Arianna Giovannini、Diego Savoia、Achille Umani-Ronchi

  DOI：10.1021/jo00262a048

  日期：1989.1