4-(2-Oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline | 146041-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(2-Oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-(1,2,3,4-Tetrahydroquinolin-4-yl)pyrrolidin-2-one
• CAS: 146041-90-9
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: PVDVYUUMBNKLDR-UHFFFAOYSA-N

物化性质

• 沸点：
  406.7±44.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-Oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.34h， 生成 1-(N-ethyl-N-methylamino)-7-(pyrrolidin-1-yl)julolidine
  参考文献：
  名称：

  使用苯并三唑方法方便地合成Julolidines。

  摘要：

  N，N-双[（苯并三唑-1-基）甲基]苯胺（2）与1-乙烯基吡咯烷-2-酮的反应得到非对映异构体1,7-双（2-氧代吡咯烷-1-基）-1假核苷的混合物在用LAH还原3后，分离出主要的1,7-二（吡咯烷-1-基）氟尿烷（4）的反式非对映异构体。2与乙基乙烯基醚的反应主要产生反式1,7-二（苯并三唑-1-基）甲氧萘啶（11）。由四氢喹啉15逐步合成可得到在C-1和C-7上具有两个不同取代基的聚甲基吡啶。1-[（（苯并三唑-1-基）甲基] -1，2，3，4-四氢喹啉（25）与可烯醇化的醛的反应得到四氢喹啉26-29的混合物，经氢化钠处理后将其转变成单一的聚idine啶产品，LAH或苯基溴化镁。1,2,3的反应

  DOI：

  10.1021/jo9519118
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 N-(1H-苯并三唑-1-基甲基)苯胺 在 对甲苯磺酸 作用下， 以65%的产率得到4-(2-Oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Additions of 1-(aminomethyl)benzotriazoles to enamines, enamides, and vinyl ethers: novel routes to 1,3-diamines and tetrahydroquinolines

  摘要：

  New methods for the synthesis of 1,3-diamines and of 4-substituted tetrahydroquinolines are described in which the key step is the addition of the condensation products derived from amines, aldehydes, and benzotriazole to enamines, enamides, and vinyl ethers.

  DOI：

  10.1021/jo00056a006

文献信息

• Reactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2-Azabutadienes. Synthesis of 1,2, 3,4-Tetrahydroquinolines and 1,2-Dihydroquinolines via a Hetero Diels-Alder Reaction
  作者：William H. Pearson、Wen-Kui Fang

  DOI：10.1002/ijch.199700007

  日期：——

  rearrangement of benzylic azides and (2) the intermolecular Schmidt reactions of azides XN3 (X = aliphatic) with benzylic carbocations derived from benzylic alcohols ArCH(R)OH. The iminium ions ArN+(X)=CHR behave as cationic 2-azabutadienes in the presence of alkenes and alkynes, producing 1,2, 3,4-tetrahydroquinolines and 1,2-dihydroquinolines by a hetero Diels–Alder reaction.

  报道了两种生成ArN +（X）= CHR（X = H或烷基，R = H或烷基）类型的亚胺离子的方法：（1）布朗斯台德酸促进的苄基叠氮化物重排和（2 ）叠氮化物XN 3（X =脂族基）与衍生自苄基醇ArCH（OH）的苄基碳阳离子的分子间Schmidt反应。亚胺离子ArN +（X）= CHR在烯烃和炔烃的存在下表现为阳离子2-氮杂丁二烯，通过杂Diels-Alder反应生成1,2，3,4-四氢喹啉和1,2-二氢喹啉。
• Reactions of N-Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinylamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00118a014

  日期：1995.6

  Reactions of N-alkyl-N-phenyl-1H-benzotriazole-1-methanamines 1 with N-vinyl-2-pyrrolidinone and with N-vinyl-N-methylacetamide give 4-(2-pyrrolidinon-1-yl)- and 4-(N-methylacetamido-N-yl)-1,2,3 ,4-tetrahydroquinolines (5 and 32), respectively. In a reaction with N-vinyl-2-pyrrolidinone, alpha-alkyl (11) and alpha-aryl(18) derivatives of 1 stereoselectively give cis-2,4-disubstituted tetrahydroquinolines 16 and 21, respectively. The 2-pyrrolidinon-1-yl and acetamido-N-yl substituents in the products are reduced with lithium aluminum hydride to the corresponding amino groups. Similar reactions of N-phenyl-1H-benzotriazole-1-methanamines 1 with 9-vinylcarbazole (40) lead to the corresponding 4-(carbazol-9-yl)-1,2,3,4-tetrahydroquinolines (41 and 42) and/or analogous 4-(benzotriazol-1-yl) or 4-(benzotriazol-2-yl) derivatives (37, 38, 43, and 44), depending on the nature of the starting material and the reaction conditions. By commencing with aniline derivatives in which the nitrogen atom is built into a heterocyclic system, this method allows for the addition of a another ring to the system, as exemplified by the conversion of phenothiazine into 46 and [3,1]benzoxazine into 49, 52, and 53.