2-<1-(1,2,3,4-tetrahydro)quinolino>acetophenone | 5653-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<1-(1,2,3,4-tetrahydro)quinolino>acetophenone
• 英文别名: 1,2,3,4-tetrahydro-1-phenacylquinoline；2-(3,4-dihydro-2H-[1]quinolyl)-1-phenyl-ethanone；2-(3,4-Dihydro-2H-[1]chinolyl)-1-phenyl-aethanon；2-(3,4-dihydro-2H-quinolin-1-yl)-1-phenylethanone
• CAS: 5653-12-3
• 化学式: C₁₇H₁₇NO
• mdl: MFCD12645873
• 分子量: 251.328
• InChiKey: YXDGQXQPNSTFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<1-(1,2,3,4-tetrahydro)quinolino>acetophenone 以4%的产率得到
  参考文献：
  名称：

  HILL, J.;ZAKARIA, M. M.;MUMFORD, D., J. CHEM. SOC. PERKIN TRANS., 1983, N 10, 2455-2458

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-丙炔基)苯胺 在 2-二环己基膦-2′,4′,6′-三异丙基联苯金(I) 双(三氟甲烷磺酰)亚胺 、 二氢吡啶 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 2-<1-(1,2,3,4-tetrahydro)quinolino>acetophenone
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular Hydroarylation and Transfer Hydrogenation of N-Aryl Propargylamines to Construct Tetrahydroquinolines and 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolines

  摘要：

  DOI：

  10.1021/acs.joc.3c01214

文献信息

• NH₄PF₆-promoted cyclodehydration of α-amino carbonyl compounds: efficient synthesis of pyrrolo[3,2,1-ij]quinoline and indole derivatives
  作者：Xiao-Ming Ji、Shu-Juan Zhou、Chen-Liang Deng、Fan Chen、Ri-Yuan Tang

  DOI：10.1039/c4ra11168k

  日期：——

  NH4PF6 is an inexpensive, safe, and low-toxicity inorganic salt; it was found to promote the cyclodehydration of α-amino carbonyl compounds in the absence of metal reagents. This simple cyclodehydration strategy enables highly atom-economic formation of pyrrolo[3,2,1-ij]quinoline and indole derivatives, which are significant pharmacophores.

  NH 4 PF 6是一种廉价，安全且低毒的无机盐；发现在不存在金属试剂的情况下可促进α-氨基羰基化合物的环脱水。这种简单的环脱水策略使吡咯并[3,2,1- ij ]喹啉和吲哚衍生物具有很高的原子经济性，这是重要的药效团。
• Cyclometalated Ruthenium Catalyst Enables Selective Oxidation of <i>N</i>-Substituted Tetrahydroquinolines to Lactams
  作者：Monuranjan Konwar、Tapashi Das、Animesh Das

  DOI：10.1021/acs.orglett.3c04263

  日期：2024.2.16

  Herein, we report an unusual α-methylene oxidation of N-substituted tetrahydroquinoline to lactams using the cyclometalated Ru(II)-complex as a catalyst. Cyclic-α-methylene C–H bonds are selectively oxidized under the reaction conditions even in the presence of α-methyl or reactive α-methylene C–H bonds. This methodology is also useful in the late-stage functionalization of pharmaceuticals. Mechanistic

  在此，我们报道了使用环金属化 Ru(II)-络合物作为催化剂， N-取代的四氢喹啉发生不寻常的 α-亚甲基氧化成内酰胺的情况。即使存在 α-甲基或反应性 α-亚甲基 C-H 键，环状 α-亚甲基 C-H 键也会在反应条件下被选择性氧化。这种方法在药物的后期功能化中也很有用。机理研究表明，高价Ru(VI)-顺式-二氧代物质在控制选择性方面发挥着重要作用。
• Kunckell, Chemische Berichte, 1897, vol. 30, p. 576
  作者：Kunckell

  DOI：——

  日期：——
• Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones
  作者：Eric Brown、Antoine Lézé、Joël Touet

  DOI：10.1016/0957-4166(96)00245-5

  日期：1996.7

  LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six alpha-aminophenones 4-9 into the corresponding optically active beta-aminoalcohols 10-15 whose ee's were in the range 40-97% after chromatography and recrystallization. The asymmetric reduction of the ortho-dimethylaminobenzophenone 18, using the same reducing agents afforded the enantiomerically pure benzhydrols (R)-(-)-19 and (S)-(+)-19, respectively, and in 86-100% yields. The ortho-aminobenzhydrol (S)-(+)-20 and a-fluorenyl ethanol (R)-(+)-23 and (S)-(-)-23 were similarly obtained from the corresponding ketones 17 and 25, respectively. The latter carbinols were obtained in an enantiomerically pure state after recrystallization. Copyright (C) 1996 Elsevier Science Ltd
• Hill, John; Zakaria, Marwan M.; Mumford, David, Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2455 - 2458
  作者：Hill, John、Zakaria, Marwan M.、Mumford, David

  DOI：——

  日期：——